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DOI: 10.1055/a-1988-5764
Palladium-Catalyzed Transfer Hydrogenation and Acetylation of N-Heteroarenes with Sodium Hydride as the Reductant
This work was supported by the National Natural Science Foundation of China (22271206 and 22071053), Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission, grant 2021 Sci & Tech 03-28), East China University of Science and Technology, the ‘111’ Project and PAPD (A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions).
Abstract
An efficient and convenient palladium-catalyzed reductive system by employing sodium hydride as the hydrogen donor and acetic anhydride as an activator has been developed for transfer hydrogenation and acetylation of a wide range of N-heteroarenes including quinoline, phthalazine, quinoxaline, phenazine, phenanthridine, and indole. Moreover, acridine substrates could be directly reduced without the use of acetic anhydride. This protocol provides a simple method for the preparation of various saturated N-heterocycles.
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Nitrogen heterocycles such as 1,2,3,4-tetrahydroquinoline (THQ) and indoline are widely occurring privileged structures existing in many natural products, pharmaceuticals, agrochemicals, and fragrances;[1] for example, schistosomicide agent oxamniquine,[2] antibacterial agent flumequine,[3] alkaloid galipinine,[4] CETP inhibitor torcetrapib,[5] (+)-yatakemycin,[6] and others. Nowadays a great number of methods have been developed to prepare these saturated N-heterocycles.[7] [8] Among the strategies, direct reduction of the corresponding unsaturated N-heteroarenes provides an efficient and concise way to access this kind of compounds.[8] In this field, catalytic hydrogenation and transfer hydrogenation play equally important roles to achieve the chemoselective reduction processes. For catalytic hydrogenation, it has been well-established using molecular hydrogen under the catalysis of various transition metals such as Rh,[9] Ru,[10] Ir,[11] Pt,[12] Pd,[13] Co,[14] Ni,[15] Fe,[16] Mo,[17] and even the very recently reported Mn[18] by Beller group and Liu group. One of the disadvantages for catalytic hydrogenation lies in the use of flammable and high-pressure hydrogen gas. Alternatively, transfer hydrogenation could be operated under relatively milder and safer reaction conditions by employing suitable hydrogen donors as reductant. To this end, great efforts have been devoted to investigating and evaluating diverse reducing agents, with several of them identified to exhibit good reactivities in hydrogenation of a wide range of N-heteroaromatic structures. The successful reducers developed to date include formic acid,[19] hydrosilanes,[20] hydroboranes,[21] Hantzsch ester,[22] alcohols,[23] and ammonia borane[24] (Scheme [1a]). Nevertheless, the exploration of new hydrogen donors for facile, mild and selective reduction of various N-heteroarenes is still desirable.
Traditionally, sodium hydride (NaH) is employed as a Brønsted base for deprotonation of acidic substrates. Our group has revealed that NaH could be activated as a reductant under the catalysis of palladium salt, to achieve a series of reduction reactions including debenzylation and deallylation,[25a] 1,4-conjugate reductions of α,β-unsaturated carbonyl compounds,[25b] and hydrodehalogenations of organic halides[25c] (Scheme [1b]). As our continuing work in this area, we report herein the reduction of several kinds of N-heteroarenes through transfer hydrogenation with the NaH/Pd reductive system. Particularly, the preparation of acetylated product could be achieved by this method (Scheme [1c]).
We began the initial investigation with quinoline (1a) as the model substrate. It should be noted that the addition of acetic anhydride was necessary to form reactive quinolinium species in situ, thus affording acetylated THQ 2a as the final product (Table [1]). The reaction was first performed with NaH (6.0 equiv) and Ac2O (2.0 equiv) in 1,4-dioxane at 60 °C in the presence of 10 mol% of various transition metal catalysts (Table [1], entries 1–7). Although ruthenium, rhodium, nickel, and iron were incapable of promoting the reaction (entries 1-4), to our delight, the use of three palladium catalysts could generate the desired product 2a in 38–60% yields (entries 5–7). The loading of Ac2O was then optimized (entries 7–11), giving the best yield (98%) when five equivalents of Ac2O was used (entry 11). A survey of the reaction medium indicated that 1,4-dioxane was still the choice of solvent (entries 11–14). Further optimization by adjusting the dosage of NaH failed to improve the efficiency of the reaction (entries 15–18). Eventually, screening of the catalyst loading (entries 19–21) and reaction temperature (entries 22, 23) could not provide better result than entry 11. Notably, scale-up of 1a to one gram level by using 5 mol% PdCl2 as the catalyst gave product 2a in 79% yield (entry 24).
a Reaction conditions, unless otherwise specified: NaH (4.0–8.0 equiv) and catalyst (10 mol%) in solvent (1.0 mL) was stirred at rt for 5 min before Ac2O and 1a (0.5 mmol) in solvent (0.5 mL) was added, and then the reaction was stirred at 60 °C for 12 h.
b NR: No reaction.
c PdCl2 (5 mol%) was used.
d PdCl2 (20 mol%) was used.
e The reaction was conducted at 40 °C.
f The reaction was conducted at 80 °C.
g Quinoline (1a; 8 mmol, 1.03 g) and PdCl2 (5 mol%) were used.
With the optimal reaction conditions in hand, we investigated the substrate scope of the transfer hydrogenation reaction (Scheme [2]). The scope of the N-heteroarenes was quite broad. Quinolines 1a–1j, phthalazine (1k), quinoxaline (1l), phenazine (1m), phenanthridines 1n–p, and indoles 1q–u are all suitable substrates for this reaction. The quinolines having different substituents at various positions were first surveyed. It was found that MeO, F, Ph, ArO, Me2N, and Me groups could survive under the reaction conditions to afford the desired products 2a–j in moderate to excellent yields. Notably, sterically hindered 3-phenylquinoline reacted well to give the 3-phenyl Ac-THQ 2h in 35% yield. When phthalazine (1k) was subjected to the standard reaction conditions, only one C=N bond was selectively reduced to generate compound 2k as the single product. By comparison, treatment of quinoxaline (1l) with NaH/Ac2O/PdCl2 gave the diacetylated product 2l with both C=N moieties completely reduced. Interestingly, phenazine (1m) underwent the reaction smoothly to deliver a monoacetylated product 2m in high yield. In addition, three phenanthridine substrates 1n–1p and five indole substrates 1q–u were tested, providing the corresponding acetylated reduction products 2n–u in low to high yields. The reason for low to moderate yields of 2p–u was due to the incomplete conversion of the starting materials 1p–u. Some N-heteroarenes could not match the reductive system. For example, when pyridine (1v), isoquinoline (1w), and 2-methylquinoline (1x) were used as the substrates, no desired product was detected under the reaction conditions, probably because it is difficult for dearomatization of these structures.
a Reaction conditions: NaH (2.2–4.0 equiv) and catalyst (10 mol%) in solvent (1.0 mL) was stirred at rt for 5 min before 3a (0.3 mmol) was added, then the reaction was stirred at 60 °C for the specified time.
We found that acridine was easier to be reduced than N-heteroarenes listed in Scheme [2]. As a result, no acetic anhydride was required to promote the reduction of acridine. In order to establish the optimal reaction conditions, some experiments were carried out using NaH (4 equiv) in DMF (Table [2]). Different from the reduction of quinoline, several transition metals including palladium could catalyze the direct reduction of acridine, such as CoCl2·6H2O (10% yield, Table [2], entry 1), RhCl3·3H2O (58% yield, entry 2) and RuCl3·3H2O (57% yield, entry 3). Nevertheless, after screening several palladium salts, Pd(OAc)2 was identified as the best catalyst, producing 9,10-dihydroacridine 4a in 75% yield (entry 7). Further optimization of the solvent and loading of NaH improved the reaction yield to 96% (entry 13).
Next, the generality of the reaction was evaluated. As shown in Scheme [3, a] range of acridines bearing Me, MeO, and MeS substituents could participate in the process to afford products 4a–i in 41–96% yields. The limitation of the method was also realized. That is, some reducible functional groups, such as Br, Cl, CN, CHO, and BnO, were not compatible with the reaction conditions, usually leading to the generation of a complex reaction mixture.
Based on our experimental results and previous literature reports,[19] a proposed reaction mechanism is shown in Scheme [4]. First, quinoline 1a was acetylated by Ac2O to give quinolinium 5, which underwent the 1,4-addition reaction with Pd-H complex to afford the dihydroquinoline intermediate 6. Isomerization of the double bond in 6 and the following 1,2-addition generated the final product 2a. By comparison, in the case of acridine, the 1,4-reductive addition of 3a could directly provide 9,10-dihydroacridine 4a.
In summary, we have developed a reductive system by employing NaH as hydrogen donor and palladium as catalyst, which was used here for transfer hydrogenation of a wide range of N-heteroarenes including quinoline, phthalazine, quinoxaline, phenazine, phenanthridine, indole, and acridine, generating the corresponding acetylated reduction products or direct reduction products in acceptable to excellent yields. All reagents used in the reaction are readily available in a chemical laboratory, therefore providing a simple method for the preparation of saturated N-heterocycles.
Unless otherwise indicated, all glassware was oven dried by a heat gun before use and all reactions were performed under an atmosphere of N2. All solvents were distilled from appropriate drying agents prior to use. All reagents were used as received from commercial suppliers, unless otherwise stated. Reaction progress was monitored by TLC performed on glass plates coated with silica gel GF254 with 0.2 mm thickness. Chromatograms were visualized by fluorescence quenching with UV light at 254 nm or by staining using aq KMnO4. Flash column chromatography was performed using silica gel 60 (200–300 mesh). Mass spectra were obtained using a TOF MS instrument ESI source. All 1H and 13C NMR spectra were recorded on Bruker AV-400 or AV-600, and Agilent AV-400 spectrometers. Spectra were referenced using the residual solvent peaks of the respective solvent: CDCl3 (δ = 7.26 for 1H NMR and δ = 77.16 for 13C NMR), DMSO-d 6 (δ = 2.50 for 1H NMR and δ = 39.52 for 13C NMR). Coupling constants J were quoted in Hz. 1H NMR spectroscopy splitting patterns were designated as singlet (s), doublet (d), triplet (t). Splitting patterns that could not be interpreted or easily visualized were designated as multiplet (m).
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Reduction and Acetylation of Various N-Heteroarenes; General Procedure
A mixture of NaH (60% dispersion in mineral oil; 120.0 mg, 3.0 mmol,) and PdCl2 (9.0 mg, 0.05 mmol) in 1,4-dioxane (1 mL) was stirred at rt for 5 min before Ac2O (237 μL, 2.5 mmol) and N-heteroarene 1 (0.5 mmol) in 1,4-dioxane (0.5 mL) were added. After that, the mixture was warmed to 60 °C. After stirring for 12 h, to the mixture was added sat. aq NH4Cl (3 mL) at 0 °C. The resulting mixture was then extracted with EtOAc (3 × 3 mL). The combined extracts were dried (Na2SO4) and concentrated under vacuum. The resulting residue was purified by silica gel chromatography affording the desired hydrogenated Ac-N-heteroarene 2.
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1-(3,4-Dihydroquinolin-1(2H)-yl)ethan-1-one (2a)
Following the general procedure, the title compound was obtained as a yellow oil; yield: 85.7 mg (98%).
Following the general procedure, when 1a (1.03 g, 8 mmol) was used in this reaction, 2a was obtained in 79% (1.11 g) yield.
1H NMR (400 MHz, CDCl3): δ = 7.23–7.09 (m, 4 H), 3.79 (t, J = 5.9 Hz, 2 H), 2.71 (t, J = 6.0 Hz, 2 H), 2.23 (s, 3 H), 2.02–1.86 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 170. 2, 139.4, 133.8, 128.5, 126.2, 125.3, 124.7, 43.0, 27.0, 24.2, 23.3.
The 1H and 13C NMR of 2a are consistent with the reported spectra.[26]
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1-(6-Methoxy-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2b)
Similar to the general procedure, the reaction was performed at 80 °C for 24 h and the title compound was obtained as a yellow oil; yield: 63.4 mg (62%).
1H NMR (400 MHz, CDCl3): δ = 6.99 (s, 1 H), 6.81–6.63 (m, 2 H), 3.84–3.73 (m, 2 H), 3.79 (s, 3 H), 2.67 (t, J = 6.4 Hz, 2 H), 2.18 (s, 3 H), 1.98–1.88 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 170.1, 157.1, 135.3, 132.7, 125.5, 113.4, 111.5, 55.5, 42.5, 27.2, 24.0, 23.0.
HRMS (ESI): m/z [M + H]+ calcd for C12H16NO2: 206.1181; found: 206.1185.
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1-(6-Fluoro-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2c)
Similar to the general procedure, the reaction was performed at 60 °C for 24 h and the title compound was obtained as a colorless oil; yield: 58.3 mg (60%).
1H NMR (400 MHz, CDCl3): δ = 7.04 (s, 1 H), 6.93–6.78 (m, 2 H), 3.77 (t, J = 6.2 Hz, 2 H), 2.71 (t, J = 6.4 Hz, 2 H), 2.20 (s, 3 H), 2.05–1.84 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 169.9, 159.9 (d, J = 245.4 Hz), 135.5 126.0, 114.9 (d, J = 22.2 Hz), 112.8 (d, J = 22.5 Hz), 42.4, 27.0 (d, J = 1.1 Hz), 23.8, 23.0.
HRMS (ESI): m/z [M + H]+ calcd for C11H13FNO: 194.0981; found: 194.0984.
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1-(5-Phenyl-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2d)
Similar to the general procedure, the reaction was performed at 60 °C for 24 h and the title compound was obtained as a yellow oil; yield: 105.7 mg (84%).
1H NMR (400 MHz, CDCl3): δ = 7.49–7.21 (m, 7 H), 7.13 (d, J = 6.7 Hz, 1 H), 3.79 (t, J = 6.5 Hz, 2 H), 2.59 (t, J = 6.2 Hz, 2 H), 2.26 (s, 3 H), 1.93–1.77 (m, 2 H).
13C NMR (151 MHz, CDCl3): δ = 170.4, 141.5, 140.6, 139.8, 132.7, 129.4, 128.4, 127.3, 126.8, 125.8, 124.2, 42.8, 24.9, 24.6, 23.3.
HRMS (ESI): m/z [M + H]+ calcd for C17H18NO: 252.1388; found: 252.1391.
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1-(5-(3-Methoxyphenoxy)-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2e)
Similar to the general procedure, the reaction was performed at 60 °C for 24 h and the title compound was obtained as a yellow solid; yield: 141.7 mg (95%).
1H NMR (400 MHz, CDCl3): δ = 7.21 (t, J = 8.5 Hz, 1 H), 7.14 (t, J = 8.0 Hz, 2 H), 6.75 (d, J = 8.3 Hz, 1 H), 6.63 (d, J = 7.8 Hz, 1 H), 6.51 (s, 2 H), 3.83–3.73 (m, 2 H), 3.78 (s, 3 H), 2.73 (t, J = 6.8 Hz, 2 H), 2.28 (s, 3 H), 2.01–1.87 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 170.1, 161.1, 158.7, 154.0, 140.9, 130.3, 126.3, 124.3, 120.4, 115.8, 109.9, 108.4, 104.0, 55.5, 43.5, 23.5, 23.4, 21.1.
HRMS (ESI): m/z [M + H]+ calcd for C18H20NO3: 298.1443; found: 298.1357.
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1-(6-(3-(Dimethylamino)phenyl)-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2f)
Similar to the general procedure, the reaction was performed at 60 °C for 16 h and the title compound was obtained as a yellow solid; yield: 132.6 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 7.47–7.35 (m, 2 H), 7.34–7.06 (m, 2 H), 6.95–6.86 (m, 2 H), 6.74 (d, J = 6.9 Hz, 1 H), 3.82 (t, J = 6.4 Hz, 2 H), 3.01 (s, 6 H), 2.79 (t, J = 6.2 Hz, 2 H), 2.28 (s, 3 H), 2.05–1.95 (m, 2 H).
13C NMR (151 MHz, CDCl3): δ = 170.2, 151.0, 141.5, 139.2, 138.4, 133.7, 129.5, 127.3, 125.0, 124.8, 115.7, 111.8, 111.3, 43.0, 40.8, 27.2, 24.2, 23.4.
HRMS (ESI): m/z [M + H]+ calcd for C19H23N2O: 295.1810; found: 295.1806.
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1-(6-(2-Methoxyphenyl)-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2g)
Similar to the general procedure, the reaction was performed at 60 °C for 16 h and the title compound was obtained as a yellow oil; yield: 121.1 mg (86%).
1H NMR (400 MHz, CDCl3): δ = 7.42–7.08 (m, 5 H), 7.06–6.95 (m, 2 H), 3.88–3.78 (m, 2 H), 3.83 (s, 3 H), 2.77 (t, J = 6.0 Hz, 2 H), 2.29 (s, 3 H), 2.05–1.93 (m, 2 H).
13C NMR (151 MHz, CDCl3): δ = 170.3, 156.5, 138.2, 135.5, 130.9, 129.9, 129.6, 128.8, 127.4, 124.1, 121.0, 111.3, 55.7, 43.0, 27.2, 24.2, 23.4.
HRMS (ESI): m/z [M + H]+ calcd for C18H20NO2: 282.1494; found: 282.1495.
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1-(3-Phenyl-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2h)
Similar to the general procedure, the reaction was performed at 60 °C for 24 h and the title compound was obtained as a yellow oil; yield: 44.3 mg (35%).
1H NMR (400 MHz, CDCl3): δ = 7.34 (t, J = 7.2 Hz, 2 H), 7.33–7.12 (m, 7 H), 4.31–4.10 (m, 1 H), 3.77–3.59 (m, 1 H), 3.20–3.02 (m, 2 H), 3.03–2.87 (m, 1 H), 2.21 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 170.2, 142.9, 139.1, 128.83, 128.82, 127.3, 127.1, 126.3, 125.3, 124.6, 49.7, 41.8, 34.8, 23.2.
HRMS (ESI): m/z [M + H]+ calcd for C17H18NO: 252.1388; found: 252.1389.
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1-(7-(p-Tolyl)-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2i)
Similar to the general procedure, the reaction was performed at 60 °C for 24 h and the title compound was obtained as a colorless oil; yield: 128.2 mg (97%).
1H NMR (400 MHz, CDCl3): δ = 7.51–7.39 (m, 2 H), 7.38–7.33 (m, 1 H), 7.32–7.18 (m, 4 H), 3.83 (t, J = 6.1 Hz, 2 H), 2.76 (t, J = 6.0 Hz, 2 H), 2.40 (s, 3 H), 2.30 (s, 3 H), 2.05–1.94 (m, 2 H).
13C NMR (151 MHz, CDCl3): δ = 170.2, 139.4, 137.7, 137.3, 129.7, 128.9, 128.1, 126.9, 123.8, 123.2, 114.4, 42.9, 26.7, 24.2, 23.4, 21.2.
HRMS (ESI): m/z [M + H]+ calcd for C18H20NO: 266.1545; found: 266.1544.
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1-(7-(4-Methoxyphenyl)-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (2j)
Similar to the general procedure, the reaction was performed at 60 °C for 24 h and the title compound was obtained as a colorless oil; yield: 132.4 mg (94%).
1H NMR (400 MHz, CDCl3): δ = 7.56–7.39 (m, 2 H), 7.37–7.24 (m, 2 H), 7.19 (d, J = 7.6 Hz, 1 H), 7.12–6.78 (m, 2 H), 3.88–3.79 (m, 2 H), 3.85 (s, 3 H), 2.76 (t, J = 6.4 Hz, 2 H), 2.30 (s, 3 H), 2.04–1.93 (m, 2 H).
13C NMR (151 MHz, CDCl3): δ = 170.2, 159.4, 139.8, 139.1, 133.2, 131.8, 128.9, 128.1, 123.6, 123.0, 114.4, 55.5, 42.9, 26.7, 24.2, 23.4.
HRMS (ESI): m/z [M + H]+ calcd for C18H20NO2: 282.1494; found: 282.1497.
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1-(Phthalazin-2(1H)-yl)ethan-1-one (2k)
Similar to the general procedure, DMA instead of 1,4-dioxane was used and the reaction was performed at 60 °C for 24 h. The title compound was obtained as a white solid; yield: 73.8 mg (85%).
1H NMR (400 MHz, CDCl3): δ = 7.46 (s, 1 H), 7.45 –7.31 (m, 1 H), 7.31–7.26 (m, 1 H), 7.23 (d, J = 7.4 Hz, 1 H), 7.15 (d, J = 7.4 Hz, 1 H), 4.97 (s, 2 H), 2.35 (s, 3 H).
13C NMR (151 MHz, CDCl3): δ = 172.7, 141.1, 131.7, 130.1, 128.3, 126.2, 126.1, 124.1, 41.7, 21.2.
HRMS (ESI): m/z [M + H]+ calcd for C10H11N2O: 175.0871; found: 175.0879.
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1,1′-(2,3-Dihydroquinoxaline-1,4-diyl)bis(ethan-1-one) (2l)
Similar to the general procedure, the reaction was performed at 60 °C for 4 h and the title compound was obtained as a white solid; yield: 96.2 mg (88%).
1H NMR (400 MHz, CDCl3): δ = 7.48–7.02 (m, 4 H), 3.95 (s, 4 H), 2.26 (s, 6 H).
13C NMR (151 MHz, CDCl3): δ = 169.4, 134.1, 125.8, 124.9, 44.9, 22.9.
HRMS (ESI): m/z [M + H]+ calcd for C12H15N2O2: 219.1134; found: 219.1137.
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1-(Phenazin-5(10H)-yl)ethan-1-one (2m)
Similar to the general procedure, DME instead of 1,4-dioxane was used and the reaction was performed at 60 °C for 24 h. The title compound was obtained as a yellow oil; yield: 101.3 mg (90%).
1H NMR (400 MHz, DMSO-d 6): δ = 8.93 (s, 1 H), 7.24–6.81(m, 2 H), 7.10 (t, J = 7.3 Hz, 2 H), 6.90 (t, J = 7.5 Hz, 4 H), 2.10 (s, 3 H).
13C NMR (151 MHz, DMSO-d 6): δ = 169.5, 140.5, 126.5, 126.2, 125.4, 119.9, 114.2, 22.3.
The 1H and 13C NMR of 2m are consistent with the reported spectra.[27]
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1-(Phenanthridin-5(6H)-yl)ethan-1-one (2n)
Similar to the general procedure, DMA instead of 1,4-dioxane was used and the reaction was performed at 60 °C for 24 h. The title compound was obtained as a colorless oil; yield: 95.3 mg (85%).
1H NMR (400 MHz, CDCl3): δ = 7.82–7.76 (m, 2 H), 7.48–7.23 (m, 6 H), 4.94 (s, 2 H), 2.19 (s, 3 H).
13C NMR (151 MHz, CDCl3): δ = 169.6, 138.2, 135.3, 131.9, 129.9, 128.2, 127.9, 126.43, 126.35, 124.7, 124.6, 123.4, 45.1, 22.4.
The 1H and 13C NMR of 2n are consistent with the reported spectra.[28]
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1-(2-Methylphenanthridin-5(6H)-yl)ethan-1-one (2o)
Similar to the general procedure, the reaction was performed at 60 °C for 22 h and the title compound was obtained as a colorless oil; yield: 87.8 mg (74%).
1H NMR (400 MHz, CDCl3): δ = 7.77 (d, J = 7.6 Hz, 1 H), 7.60 (s, 1 H), 7.41–7.27 (m, 1 H), 7.27–7.26 (m, 2 H), 7.24–7.12 (m, 2 H), 4.92 (s, 2 H), 2.44 (s, 3 H), 2.17 (s, 3 H).
13C NMR (151 MHz, CDCl3): δ = 169.6, 136.1, 135.7, 135.3, 131.9, 129.6, 128.5, 128.03, 128.00, 126.3, 125.1, 124.4, 123.3, 45.1, 22.2, 21.3.
HRMS (ESI): m/z [M + H]+ calcd for C16H16NO: 238.1232; found: 238.1237.
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1-(2-Methoxyphenanthridin-5(6H)-yl)ethan-1-one (2p)
Similar to the general procedure, DMA instead of 1,4-dioxane was used and the reaction was performed at 60 °C for 32 h. The title compound was obtained as a colorless oil; yield: 63.7 mg (50%).
1H NMR (400 MHz, CDCl3): δ = 7.75 (d, J = 7.6 Hz, 1 H), 7.41–7.36 (m, 1 H), 7.36–7.26 (m, 3 H), 7.18 (d, J = 8.6 Hz, 1 H), 6.88 (d, J = 8.1 Hz, 1 H), 4.92 (s, 2 H), 3.90 (s, 3 H), 2.14 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 169.7, 158.0, 135.6, 131.9, 131.5, 131.1, 128.3, 128.1, 126.4, 125.7, 123.4, 113.3, 109.7, 55.7, 45.3, 22.2.
HRMS (ESI): m/z [M + H]+ calcd for C16H16NO2: 254.1181; found: 254.1178.
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1-(Indolin-1-yl)ethan-1-one (2q)
Similar to the general procedure, the reaction was performed at 60 °C for 36 h and the title compound was obtained as a colorless oil; yield: 55.1 mg (68%).
1H NMR (400 MHz, CDCl3): δ = 8.26–8.18 (m, 1 H), 7.25–7.14 (m, 2 H), 7.09–6.86 (m, 1 H), 4.04 (t, J = 8.5 Hz, 2 H), 3.19 (t, J = 8.4 Hz, 2 H), 2.22 (s, 3 H).
13C NMR (151 MHz, CDCl3): δ = 168.8, 143.0, 131.2, 127.6, 124.6, 123.6, 117.0, 48.8, 28.1, 24.3.
The 1H and 13C NMR of 2q are consistent with the reported spectra.[29]
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1-(6-Fluoroindolin-1-yl)ethan-1-one (2r)
Similar to the general procedure, the reaction was performed at 60 °C for 36 h and the title compound was obtained as a colorless oil; yield: 41.6 mg (46%).
1H NMR (400 MHz, CDCl3): δ = 7.96 (d, J = 10.4 Hz, 1 H), 7.11–6.99 (m, 1 H), 6.74–6.65 (m, 1 H), 4.09 (t, J = 8.4 Hz, 2 H), 3.15 (t, J = 8.3 Hz, 2 H), 2.22 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 169.0, 162.4 (d, J = 242.4 Hz), 144.1 (d, J = 12.0 Hz), 126.4 (d, J = 3.0 Hz), 124.9 (d, J = 10.0 Hz), 110.0 (d, J = 23.0 Hz), 105.1 (d, J = 28.0 Hz), 49.7, 27.4, 24.2.
The 1H and 13C NMR of 2r are consistent with the reported spectra.[29]
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1-(7-Methylindolin-1-yl)ethan-1-one (2s)
Similar to the general procedure, the reaction was performed at 60 °C for 36 h and the title compound was obtained as a colorless oil; yield: 29.3 mg (33%).
1H NMR (400 MHz, CDCl3): δ = 7.09–6.89 (m, 3 H), 4.08 (t, J = 7.1 Hz, 2 H), 3.02 (t, J = 7.1 Hz, 2 H), 2.27 (s, 6 H).
13C NMR (101 MHz, CDCl3): δ = 168.6, 141.7, 134.5, 129.9, 128.8, 125.2, 121.8, 51.2, 30.1, 23.8, 20.7.
The 1H and 13C NMR of 2s are consistent with the reported spectra.[30]
#
1-(3-Methylindolin-1-yl)ethan-1-one (2t)
Similar to the general procedure, the reaction was performed at 60 °C for 36 h and the title compound was obtained as a colorless oil; yield: 38.8 mg (44%).
1H NMR (400 MHz, CDCl3): δ = 8.19 (d, J = 8.0 Hz, 1 H), 7.23–7.14 (m, 2 H), 7.04 (t, J = 7.4 Hz, 1 H), 4.26–4.16 (m, 1 H), 3.62–3.45 (m, 2 H), 2.22 (s, 3 H), 1.36 (d, J = 6.7 Hz, 3 H).
13C NMR (101 MHz, CDCl3): δ = 168.7, 142.5, 136.4, 127.8, 123.8, 123.5, 117.0, 57.1, 34.9, 24.3, 20.4.
The 1H and 13C NMR of 2t are consistent with the reported spectra.[29]
#
1-(2-Methylindolin-1-yl)ethan-1-one (2u)
Similar to the general procedure, the reaction was performed at 60 °C for 36 h and the title compound was obtained as a colorless oil; yield: 6.2 mg (7%).
1H NMR (400 MHz, CDCl3): δ = 8.15 (d, J = 7.6 Hz, 1 H), 7.21–7.14 (m, 2 H), 7.04–6.97 (m, 1 H), 4.53–4.33 (m, 1 H), 3.45–3.32 (m, 1 H), 2.70–2.58 (m, 1 H), 2.26 (s, 3 H), 1.30–1.22 (m, 3 H).
13C NMR (101 MHz, CDCl3): δ = 168.3, 141.6, 130.3, 127.5, 124.9, 123.8, 117.9, 56.3, 36.4, 23.3, 21.7.
The 1H and 13C NMR of 2u are consistent with the reported spectra.[29]
#
Reduction of Acridines; General Procedure
A mixture of NaH (60% dispersion in mineral oil; 27 mg, 0.66 mmol) and Pd(OAc)2 (7.0 mg, 0.03 mmol) in DMF (1 mL) was stirred at rt for 5 min before acridine 3 (0.3 mmol) was added. After that, the mixture was warmed to 60 °C. After stirring for 24 h, to the mixture was added sat. aq NH4Cl (3 mL) at 0 °C. The resulting mixture was then extracted with EtOAc (3 × 3 mL). The combined extracts were dried (Na2SO4) and concentrated under vacuum. The resulting residue was purified by silica gel chromatography affording the desired hydrogenated acridine 4.
#
9,10-Dihydroacridine (4a)
Following the general procedure, the title compound was obtained as a yellow oil; yield: 51.8 mg (96%).
1H NMR (400 MHz, CDCl3): δ = 7.21–7.02 (m, 4 H), 6.86 (t, J = 7.3 Hz, 2 H), 6.68–6.56 (m, 2 H), 5.95 (s, 1 H), 4.06 (s, 2 H).
13C NMR (101 MHz, CDCl3): δ 140.2, 128.7, 127.1, 120.8, 120.2, 113.6, 31.5.
The 1H and 13C NMR of 4a are consistent with the reported spectra.[31]
#
9-Methyl-9,10-dihydroacridine (4b)
Following the general procedure, the title compound was obtained as a yellow oil; yield: 55.4 mg (95%).
1H NMR (400 MHz, CDCl3): δ = 7.17 (d, J = 7.4 Hz, 2 H), 7.10 (t, J = 7.4 Hz, 2 H), 6.90 (t, J = 7.3 Hz, 2 H), 6.71 (d, J = 7.9 Hz, 2 H), 6.04 (s, 1 H), 4.11 (q, J = 7.0 Hz, 1 H), 1.36 (d, J = 7.1 Hz, 3 H).
13C NMR (151 MHz, CDCl3): δ = 139.2, 128.3, 127.0, 125.8, 120.9, 113.6, 36.9, 26.6.
The 1H and 13C NMR of 4b are consistent with the reported spectra.[32]
#
4-Methyl-9,10-dihydroacridine (4c)
Similar to the general procedure, the reaction was performed at 60 °C for 22 h and the title compound was obtained as a yellow oil; yield: 52.5 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 7.23–7.02 (m, 2 H), 7.01–6.90 (m, 2 H), 6.89–6.81 (m, 1 H), 6.82–6.71 (m, 2 H), 5.91 (s, 1 H), 4.07 (s, 2 H), 2.27 (s, 3 H).
13C NMR (151 MHz, CDCl3): δ = 140.2, 138.4, 128.6, 128.4, 127.1, 126.6, 120.9, 120.5, 120.4, 120.2, 119.6, 114.0, 31.7, 17.0.
The 1H and 13C NMR of 4c are consistent with the reported spectra.[33]
#
3-Methyl-9,10-dihydroacridine (4d)
Similar to the general procedure, the reaction was performed at 60 °C for 23 h and the title compound was obtained as a yellow oil; yield: 42.6 mg (73%).
1H NMR (400 MHz, CDCl3): δ = 7.24–7.03 (m, 2 H), 7.02–6.99 (m, 1 H), 6.87–6.79 (m, 1 H), 6.74–6.07 (m, 2 H), 6.50 (s, 1 H), 5.89 (s, 1 H), 4.03 (s, 2 H), 2.28 (s, 3 H).
13C NMR (151 MHz, CDCl3): δ = 140.3, 140.1, 136.9, 128.8, 128.6, 127.0, 121.6, 120.6, 120.4, 117.2, 114.2, 113.6, 31.1, 21.3.
The 1H and 13C NMR of 4d are consistent with the reported spectra.[34]
#
1,3-Dimethyl-9,10-dihydroacridine (4e)
Similar to the general procedure, the reaction was performed at 60 °C for 26 h and the title compound was obtained as a yellow oil; yield: 37.8 mg (60%).
1H NMR (400 MHz, CDCl3): δ = 7.23–7.01 (m, 2 H), 6.89–6.77 (m, 1 H), 6.64–6.53 (m, 1 H), 6.55 (s, 1 H), 6.32 (s, 1 H), 5.82 (s, 1 H), 3.98 (s, 2 H), 2.37–2.16 (m, 6 H).
13C NMR (151 MHz, CDCl3): δ = 134.0, 139.7, 136.7, 136.4, 129.1, 127.1, 123.0, 120.3, 119.9, 115.6, 113.3, 112.1, 28.5, 21.1, 19.4.
HRMS (ESI): m/z [M + H]+ calcd for C15H16N: 210.1283; found: 210.1285.
#
2-Methoxy-9,10-dihydroacridine (4f)
Similar to the general procedure, the reaction was performed at 60 °C for 6 h and the title compound was obtained as a yellow oil; yield: 36.3 mg (57%).
1H NMR (400 MHz, CDCl3): δ = 7.16–7.05 (m, 2 H), 6.82–6.79 (m, 1 H), 6.73–6.58 (m, 4 H), 5.82 (s, 1 H), 4.04 (s, 2 H), 3.77 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 154.3, 140.7, 134.2, 128.7, 127.1, 121.2, 120.4, 119.4, 114.2, 114.1, 113.5, 112.8, 55.9, 31.9.
The 1H and 13C NMR of 4f are consistent with the reported spectra.[35]
#
1,3-Dimethoxy-9,10-dihydroacridine (4g)
Following the general procedure, the title compound was obtained as a yellow oil; yield: 38.1 mg (53%).
1H NMR (400 MHz, CDCl3): δ = 7.13–7.00 (m, 2 H), 6.86–6.76 (m, 1 H), 6.59 (d, J = 7.8 Hz, 1 H), 6.02 (d, J = 1.2 Hz, 1 H), 5.85 (s, 2 H), 3.95 (s, 2 H), 3.82 (s, 3 H), 3.78 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 159.8, 158.5, 141.0, 139.6, 129.3, 127.0, 120.7, 120.2, 113.5, 100.8, 91.3, 90.6, 55.6, 55.4, 24.9.
HRMS (ESI): m/z [M + H]+ calcd for C15H16NO2: 242.1181; found: 242.1188.
#
2-(Methylthio)-9,10-dihydroacridine (4h)
Similar to the general procedure, the reaction was performed at 60 °C for 36 h and the title compound was obtained as a yellow oil; yield: 37.6 mg (55%).
1H NMR (400 MHz, CDCl3): δ = 7.15–7.03 (m, 4 H), 6.86 (t, J = 7.1 Hz, 1 H), 6.71–6.57 (m, 2 H), 5.95 (s, 1 H), 4.04 (s, 2 H), 2.44 (s, 3 H).
13C NMR (151 MHz, CDCl3): δ = 139.9, 138.8, 129.8, 128.8, 128.3, 127.2, 120.9, 120.9, 119.8, 114.2, 113.6, 31.4, 18.5.
HRMS (ESI): m/z [M + H]+ calcd for C14H14NS: 228.0847; found: 228.0843.
#
1,3-Dimethoxy-6-methyl-9,10-dihydroacridine (4i)
Similar to the general procedure, the reaction was performed at 60 °C for 36 h and the title compound was obtained as a yellow oil; yield: 31.6 mg (41%).
1H NMR (400 MHz, CDCl3): δ = 6.98 (d, J = 7.5 Hz, 1 H), 6.64 (d, J = 7.5 Hz, 1 H), 6.42 (s, 1 H), 6.01 (d, J = 1.4 Hz, 1 H), 5.85–5.74 (m, 2 H), 3.91 (s, 2 H), 3.81 (s, 3 H), 3.77 (s, 3 H), 2.26 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 159.7, 158.6, 141.1, 139.4, 136.7, 129.2, 121.5, 117.2, 114.1, 101.0, 91.3, 90.5, 55.5, 55.4, 24.6, 21.2.
HRMS (ESI): m/z [M + H]+ calcd for C16H18NO2: 256.1338; found: 256.1342.
#
#
Conflict of Interest
The authors declare no conflict of interest.
Supporting Information
- Supporting information for this article is available online at https://doi-org.accesdistant.sorbonne-universite.fr/10.1055/a-1988-5764.
- Supporting Information
-
References
- 1a Zhang D, Song H, Qin Y. Acc. Chem. Res. 2011; 44: 447
- 1b Sridharan V, Suryavanshi PA, Menéndez JC. Chem. Rev. 2011; 111: 7157
- 1c Scott JD, Williams RM. Chem. Rev. 2002; 102: 1669
- 1d Katritzky R, Rachwal S, Rachwal B. Tetrahedron 1996; 52: 15031
- 1e Zhao X.-X, Guo L, Yang C, Xia W.-J. Synthesis 2021; 53: 1341
- 1f Lin Y, Li Z, Ma H, Wang Y, Wang X, Song S, Zhao L, Wu S, Tian S, Fu C, Luo L, Zhu F, He S, Zheng J, Zhang X. ChemMedChem 2020; 15: 1150
- 1g Ji X, Li Z. Med. Res. Rev. 2020; 40: 1519
- 1h Dong Y, Dong L, Chen J, Luo M, Fu X, Qiao C. Med. Chem. Res. 2018; 27: 1111
- 2 Filho RP, de Souza Menezes CM, Pinto PL. S, Paula GA, Brandt CA, da Silveira MA. B. Bioorg. Med. Chem. 2007; 15: 1229
- 3 Bálint J, Egri G, Fogassy E, Böcskei Z, Simon K, Gajáry A, Friesz A. Tetrahedron: Asymmetry 1999; 10: 1079
- 4 Rakotoson JH, Fabre N, Jacquemond-Collet I, Hanned-ouche S, Fourasté I, Moulis C. Planta Med. 1998; 64: 762
- 5 Guinó M, Phua PH, Caille JC, Hii KK. J. Org. Chem. 2007; 72: 6290
- 6 Okano K, Tokuyama H, Fukuyama T. J. Am. Chem. Soc. 2006; 128: 7136
- 7a Muthukrishnan I, Sridharan V, Menendez JC. Chem. Rev. 2019; 119: 5057
- 7b Bariwal J, Voskressensky LG, Van der Eycken EV. Chem. Soc. Rev. 2018; 47: 3831
- 7c Silva TS, Rodrigues JrM. T, Santos H, Zeoly LA, Almeida WP, Barcelos RC, Gomes RC, Fernandes FS, Coelho F. Tetrahedron 2019; 75: 2063
- 8a Zhou Y.-G. Acc. Chem. Res. 2007; 40: 1357
- 8b Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
- 8c He Y.-M, Song F.-T, Fan Q.-H. Top. Curr. Chem. 2013; 343: 145
- 8d Giustra ZX, Ishibash JS. A, Liu S.-Y. Coord. Chem. Rev. 2016; 314: 134
- 8e Yu Z.-K, Jin W.-W, Jiang Q.-B. Angew. Chem. Int. Ed. 2012; 51: 6060
- 8f Wiesenfeldt MP, Nairoukh Z, Dalton T, Glorius F. Angew. Chem. Int. Ed. 2019; 58: 10460
- 8g Glorius F. Org. Biomol. Chem. 2005; 3: 4171
- 8h Balakrishna B, Núñez-Rico JL, Vidal-Ferran A. Eur. J. Org. Chem. 2015; 5293
- 8i Chen Z.-P, Zhou Y.-G. Synthesis 2016; 48: 1769
- 9 Baralt E, Smith SJ, Hurwitz J, Horvath IT, Fish RH. J. Am. Chem. Soc. 1992; 114: 5187
- 10a Chatterjee B, Kalsi D, Kaithal A, Bordet A, Leitner W, Gunanathan C. Catal. Sci. Technol. 2020; 10: 5163
- 10b Ye TN, Li J, Kitana M, Hosono H. Green Chem. 2017; 19: 749
- 10c Ding Z.-Y, Wang T, He Y.-M, Chen F, Zhou H.-F, Fan Q.-H, Guo Q, Chan AS. C. Adv. Synth. Catal. 2013; 355: 3727
- 11a Dobereiner GE, Nova A, Schley ND, Hazari N, Miller SJ, Eisenstein O, Crabtree RH. J. Am. Chem. Soc. 2011; 133: 7547
- 11b Ji Y.-G, Wei K, Liu T, Wu L, Zhang W.-H. Adv. Synth. Catal. 2017; 359: 933
- 11c Vivancos A, Beller M, Albrecht M. ACS Catal. 2018; 8: 17
- 12a Kulkarni A, Zhou W, Török B. Org. Lett. 2011; 13: 5124
- 12b Xue X, Zeng M, Wang Y. Appl. Catal. A. 2018; 560: 37
- 13a Wang D.-S, Tang J, Zhou Y.-G, Chen M.-W, Yu C.-B, Duan Y, Jiang G.-F. Chem. Sci. 2011; 2: 803
- 13b Duan Y, Li L, Chen M.-W, Yu C.-B, Fan H.-J, Zhou Y.-G. J. Am. Chem. Soc. 2014; 136: 7688
- 13c Zhang Y, Zhu J, Xia YT, Sun XT, Wu L. Adv. Synth. Catal. 2016; 358: 3039
- 14a Xu R, Chakraborty S, Yuan H, Jones WD. ACS Catal. 2015; 5: 6350
- 14b Wei Z, Chen Y, Wang J, Su D, Tang M, Mao S, Wang Y. ACS Catal. 2016; 6: 5816
- 14c Adam R, Cabrero-Antonino JR, Spannenberg A, Junge K, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2017; 56: 3216
- 14d Sorribes I, Liu L, Doménech Carbó A, Corma A. ACS Catal. 2018; 8: 4545
- 14e Murugesan K, Chandrashekhar VG, Kreyenschulte C, Beller M, Jagadeesh RV. Angew. Chem. Int. Ed. 2020; 59: 17408
- 14f Hervochon J, Dorcet V, Junge K, Beller M, Fischmeister C. Catal. Sci. Technol. 2020; 10: 4820
- 15a Cho H, Torok F, Torok B. Org. Biomol. Chem. 2013; 11: 1209
- 15b Spadoni G, Bedini A, Lucarini S, Mari M, Caignard D, Boutin JA, Delagrange P, Lucini V, Scaglione F, Lodola A, Zanardi F, Pala D, Mor M, Rivara S. J. Med. Chem. 2015; 58: 7512
- 16 Sahoo B, Kreyenschulte C, Agostini G, Lund H, Bachmann S, Scalone M, Junge K, Beller M. Chem. Sci. 2018; 9: 8134
- 17 Zhu G, Pang K, Parkin G. J. Am. Chem. Soc. 2008; 130: 1564
- 18a Papa V, Cao Y, Spannenberg A, Junge K, Beller M. Nat. Catal. 2020; 3: 135
- 18b Liu C, Wang M, Liu S, Wang Y, Peng Y, Lan Y, Liu Q. Angew. Chem. Int. Ed. 2021; 60: 5108
- 19a Wu J, Wang C, Tang W, Pettman A, Xiao J. Chem. Eur. J. 2012; 18: 9525
- 19b Talwar D, Li HY, Durham E, Xiao J. Chem. Eur. J. 2015; 21: 5370
- 19c Tao L, Zhang Q, Li S.-S, Liu X, Liu Y.-M, Cao Y. Adv. Synth. Catal. 2015; 357: 753
- 19d Zhang L, Qiu R, Xue X, Pan Y, Xu C, Li H, Xu L. Adv. Synth. Catal. 2015; 357: 3529
- 19e Cabrero-Antonino JR, Adam R, Junge K, Jackstell R, Beller M. Catal. Sci. Technol. 2017; 7: 1981
- 19f Chen F, Sahoo B, Kreyenschulte C, Lund H, Zeng M, He L, Junge K, Beller M. Chem. Sci. 2017; 8: 6239
- 19g Guan R, Zhao H, Cao L, Jiang H, Zhang M. Org. Chem. Front. 2020; 8: 106
- 19h Ouyang L, Xia Y, Liao J, Miao R, Yang X, Luo R. ACS Omega 2021; 6: 10415
- 20a Yan M, Jin T, Chen Q, Ho HE, Fujita T, Chen L.-Y, Bao M, Chen M.-W, Asao N, Yamamoto Y. Org. Lett. 2013; 15: 1484
- 20b Liu ZY, Wen ZH, Wang XC. Angew. Chem. Int. Ed. 2017; 56: 5817
- 21a Xia Y, Sun X, Zhang L, Luo K, Wu L. Chem. Eur. J. 2016; 22: 17151
- 21b Xuan Q, Song Q. Org. Lett. 2016; 18: 4250
- 21c Yang C.-H, Chen X, Li H, Wei W, Yang Z, Chang J. Chem. Commun. 2018; 54: 8622
- 21d Pi D, Zhou H, Zhou Y, Liu Q, He R, Shen G, Uozumi Y. Tetrahedron 2018; 74: 2121
- 21e Zhou X.-Y, Chen X. Org. Biomol. Chem. 2021; 19: 548
- 22a He R, Cui P, Pi D, Sun Y, Zhou H. Tetrahedron Lett. 2017; 58: 3571
- 22b Pi D, Zhou H, Zhou Y, Liu Q, He R, Shen G, Uozumi Y. Tetrahedron 2018; 74: 2121
- 22c Bhattacharyya D, Nandi S, Adhikari P, Sarmah BK, Konwar M, Das A. Org. Biomol. Chem. 2020; 18: 1214
- 23a Alshakova ID, Gabidullin B, Nikonov GI. ChemCatChem 2018; 10: 4860
- 23b Wang Y, Huang Z, Leng X, Zhu H, Liu G, Huang Z. J. Am. Chem. Soc. 2018; 140: 4417
- 23c Grozavu A, Hepburn HB, Smith PJ, Potukuchi HK, Lindsay-Scott PJ, Donohoe TJ. Nat. Chem. 2019; 11: 242
- 23d Hepburn HB, Donohoe TJ. Chem. Eur. J. 2020; 26: 1963
- 23e Wu B, Yang J, Hu S.-B, Yu C.-B, Zhao Z.-B, Luo Y, Zhou Y.-G. Sci. China Chem. 2021; 64: 1743
- 24a Vermaak V, Vosloo HC. M, Swarts AJ. Adv. Synth. Catal. 2020; 362: 5788
- 24b Ding F, Zhang Y, Zhao R, Jiang Y, Bao RL.-Y, Lin K, Shi L. Chem. Commun. 2017; 53: 9262
- 24c Li S, Meng W, Du H. Org. Lett. 2017; 19: 2604
- 25a Mao Y, Liu Y, Hu Y, Wang L, Zhang S, Wang W. ACS Catal. 2018; 8: 3016
- 25b Liu Y, Mao Y, Hu Y, Gui J, Wang L, Wang W, Zhang S. Adv. Synth. Catal. 2019; 361: 1554
- 25c Gui J, Cai X, Chen L, Zhou Y, Zhu W, Jiang Y, Hu M, Chen X, Hu Y, Zhang S. Org. Chem. Front. 2021; 8: 4685
- 26 Bose A, Mal P. Chem. Commun. 2017; 53: 11368
- 27 Gujral J, Reddy TP, Gorachand B, Ramachary DB. ChemistrySelect 2018; 3: 7900
- 28 Shen Z, Ni Z, Mo S, Wang J, Zhu Y. Chem. Eur. J. 2012; 18: 4859
- 29 Jin N, Pan C, Zhang H, Xu P, Cheng Y, Zhu C. Adv. Synth. Catal. 2015; 357: 1149
- 30 Neufeldt SR, Seigerman CK, Sanford MS. Org. Lett. 2013; 15: 2302
- 31 Bhattacharyya D, Nandi S, Adhikari P, Sarmah BK, Konwar M, Das A. Org. Biomol. Chem. 2020; 18: 1214
- 32 Xia Y.-T, Sun X.-T, Zhang L, Luo K, Wu L. Chem. Eur. J. 2016; 22: 17151
- 33 Shamsi M, Baradarani MM, Afghan A, Joule JA. ARKIVOC 2011; (ix): 252
- 34 Cadogan JI. G, Hickson CL, Hutchison SH, McNab H. J. Chem. Soc., Perkin Trans. 1 1991; 377
- 35 Pintér Á, Klussmanna M. Adv. Synth. Catal. 2012; 354: 701
Corresponding Authors
Publication History
Received: 06 September 2022
Accepted after revision: 28 November 2022
Accepted Manuscript online:
28 November 2022
Article published online:
03 January 2023
© 2022. Thieme. All rights reserved
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-
References
- 1a Zhang D, Song H, Qin Y. Acc. Chem. Res. 2011; 44: 447
- 1b Sridharan V, Suryavanshi PA, Menéndez JC. Chem. Rev. 2011; 111: 7157
- 1c Scott JD, Williams RM. Chem. Rev. 2002; 102: 1669
- 1d Katritzky R, Rachwal S, Rachwal B. Tetrahedron 1996; 52: 15031
- 1e Zhao X.-X, Guo L, Yang C, Xia W.-J. Synthesis 2021; 53: 1341
- 1f Lin Y, Li Z, Ma H, Wang Y, Wang X, Song S, Zhao L, Wu S, Tian S, Fu C, Luo L, Zhu F, He S, Zheng J, Zhang X. ChemMedChem 2020; 15: 1150
- 1g Ji X, Li Z. Med. Res. Rev. 2020; 40: 1519
- 1h Dong Y, Dong L, Chen J, Luo M, Fu X, Qiao C. Med. Chem. Res. 2018; 27: 1111
- 2 Filho RP, de Souza Menezes CM, Pinto PL. S, Paula GA, Brandt CA, da Silveira MA. B. Bioorg. Med. Chem. 2007; 15: 1229
- 3 Bálint J, Egri G, Fogassy E, Böcskei Z, Simon K, Gajáry A, Friesz A. Tetrahedron: Asymmetry 1999; 10: 1079
- 4 Rakotoson JH, Fabre N, Jacquemond-Collet I, Hanned-ouche S, Fourasté I, Moulis C. Planta Med. 1998; 64: 762
- 5 Guinó M, Phua PH, Caille JC, Hii KK. J. Org. Chem. 2007; 72: 6290
- 6 Okano K, Tokuyama H, Fukuyama T. J. Am. Chem. Soc. 2006; 128: 7136
- 7a Muthukrishnan I, Sridharan V, Menendez JC. Chem. Rev. 2019; 119: 5057
- 7b Bariwal J, Voskressensky LG, Van der Eycken EV. Chem. Soc. Rev. 2018; 47: 3831
- 7c Silva TS, Rodrigues JrM. T, Santos H, Zeoly LA, Almeida WP, Barcelos RC, Gomes RC, Fernandes FS, Coelho F. Tetrahedron 2019; 75: 2063
- 8a Zhou Y.-G. Acc. Chem. Res. 2007; 40: 1357
- 8b Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
- 8c He Y.-M, Song F.-T, Fan Q.-H. Top. Curr. Chem. 2013; 343: 145
- 8d Giustra ZX, Ishibash JS. A, Liu S.-Y. Coord. Chem. Rev. 2016; 314: 134
- 8e Yu Z.-K, Jin W.-W, Jiang Q.-B. Angew. Chem. Int. Ed. 2012; 51: 6060
- 8f Wiesenfeldt MP, Nairoukh Z, Dalton T, Glorius F. Angew. Chem. Int. Ed. 2019; 58: 10460
- 8g Glorius F. Org. Biomol. Chem. 2005; 3: 4171
- 8h Balakrishna B, Núñez-Rico JL, Vidal-Ferran A. Eur. J. Org. Chem. 2015; 5293
- 8i Chen Z.-P, Zhou Y.-G. Synthesis 2016; 48: 1769
- 9 Baralt E, Smith SJ, Hurwitz J, Horvath IT, Fish RH. J. Am. Chem. Soc. 1992; 114: 5187
- 10a Chatterjee B, Kalsi D, Kaithal A, Bordet A, Leitner W, Gunanathan C. Catal. Sci. Technol. 2020; 10: 5163
- 10b Ye TN, Li J, Kitana M, Hosono H. Green Chem. 2017; 19: 749
- 10c Ding Z.-Y, Wang T, He Y.-M, Chen F, Zhou H.-F, Fan Q.-H, Guo Q, Chan AS. C. Adv. Synth. Catal. 2013; 355: 3727
- 11a Dobereiner GE, Nova A, Schley ND, Hazari N, Miller SJ, Eisenstein O, Crabtree RH. J. Am. Chem. Soc. 2011; 133: 7547
- 11b Ji Y.-G, Wei K, Liu T, Wu L, Zhang W.-H. Adv. Synth. Catal. 2017; 359: 933
- 11c Vivancos A, Beller M, Albrecht M. ACS Catal. 2018; 8: 17
- 12a Kulkarni A, Zhou W, Török B. Org. Lett. 2011; 13: 5124
- 12b Xue X, Zeng M, Wang Y. Appl. Catal. A. 2018; 560: 37
- 13a Wang D.-S, Tang J, Zhou Y.-G, Chen M.-W, Yu C.-B, Duan Y, Jiang G.-F. Chem. Sci. 2011; 2: 803
- 13b Duan Y, Li L, Chen M.-W, Yu C.-B, Fan H.-J, Zhou Y.-G. J. Am. Chem. Soc. 2014; 136: 7688
- 13c Zhang Y, Zhu J, Xia YT, Sun XT, Wu L. Adv. Synth. Catal. 2016; 358: 3039
- 14a Xu R, Chakraborty S, Yuan H, Jones WD. ACS Catal. 2015; 5: 6350
- 14b Wei Z, Chen Y, Wang J, Su D, Tang M, Mao S, Wang Y. ACS Catal. 2016; 6: 5816
- 14c Adam R, Cabrero-Antonino JR, Spannenberg A, Junge K, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2017; 56: 3216
- 14d Sorribes I, Liu L, Doménech Carbó A, Corma A. ACS Catal. 2018; 8: 4545
- 14e Murugesan K, Chandrashekhar VG, Kreyenschulte C, Beller M, Jagadeesh RV. Angew. Chem. Int. Ed. 2020; 59: 17408
- 14f Hervochon J, Dorcet V, Junge K, Beller M, Fischmeister C. Catal. Sci. Technol. 2020; 10: 4820
- 15a Cho H, Torok F, Torok B. Org. Biomol. Chem. 2013; 11: 1209
- 15b Spadoni G, Bedini A, Lucarini S, Mari M, Caignard D, Boutin JA, Delagrange P, Lucini V, Scaglione F, Lodola A, Zanardi F, Pala D, Mor M, Rivara S. J. Med. Chem. 2015; 58: 7512
- 16 Sahoo B, Kreyenschulte C, Agostini G, Lund H, Bachmann S, Scalone M, Junge K, Beller M. Chem. Sci. 2018; 9: 8134
- 17 Zhu G, Pang K, Parkin G. J. Am. Chem. Soc. 2008; 130: 1564
- 18a Papa V, Cao Y, Spannenberg A, Junge K, Beller M. Nat. Catal. 2020; 3: 135
- 18b Liu C, Wang M, Liu S, Wang Y, Peng Y, Lan Y, Liu Q. Angew. Chem. Int. Ed. 2021; 60: 5108
- 19a Wu J, Wang C, Tang W, Pettman A, Xiao J. Chem. Eur. J. 2012; 18: 9525
- 19b Talwar D, Li HY, Durham E, Xiao J. Chem. Eur. J. 2015; 21: 5370
- 19c Tao L, Zhang Q, Li S.-S, Liu X, Liu Y.-M, Cao Y. Adv. Synth. Catal. 2015; 357: 753
- 19d Zhang L, Qiu R, Xue X, Pan Y, Xu C, Li H, Xu L. Adv. Synth. Catal. 2015; 357: 3529
- 19e Cabrero-Antonino JR, Adam R, Junge K, Jackstell R, Beller M. Catal. Sci. Technol. 2017; 7: 1981
- 19f Chen F, Sahoo B, Kreyenschulte C, Lund H, Zeng M, He L, Junge K, Beller M. Chem. Sci. 2017; 8: 6239
- 19g Guan R, Zhao H, Cao L, Jiang H, Zhang M. Org. Chem. Front. 2020; 8: 106
- 19h Ouyang L, Xia Y, Liao J, Miao R, Yang X, Luo R. ACS Omega 2021; 6: 10415
- 20a Yan M, Jin T, Chen Q, Ho HE, Fujita T, Chen L.-Y, Bao M, Chen M.-W, Asao N, Yamamoto Y. Org. Lett. 2013; 15: 1484
- 20b Liu ZY, Wen ZH, Wang XC. Angew. Chem. Int. Ed. 2017; 56: 5817
- 21a Xia Y, Sun X, Zhang L, Luo K, Wu L. Chem. Eur. J. 2016; 22: 17151
- 21b Xuan Q, Song Q. Org. Lett. 2016; 18: 4250
- 21c Yang C.-H, Chen X, Li H, Wei W, Yang Z, Chang J. Chem. Commun. 2018; 54: 8622
- 21d Pi D, Zhou H, Zhou Y, Liu Q, He R, Shen G, Uozumi Y. Tetrahedron 2018; 74: 2121
- 21e Zhou X.-Y, Chen X. Org. Biomol. Chem. 2021; 19: 548
- 22a He R, Cui P, Pi D, Sun Y, Zhou H. Tetrahedron Lett. 2017; 58: 3571
- 22b Pi D, Zhou H, Zhou Y, Liu Q, He R, Shen G, Uozumi Y. Tetrahedron 2018; 74: 2121
- 22c Bhattacharyya D, Nandi S, Adhikari P, Sarmah BK, Konwar M, Das A. Org. Biomol. Chem. 2020; 18: 1214
- 23a Alshakova ID, Gabidullin B, Nikonov GI. ChemCatChem 2018; 10: 4860
- 23b Wang Y, Huang Z, Leng X, Zhu H, Liu G, Huang Z. J. Am. Chem. Soc. 2018; 140: 4417
- 23c Grozavu A, Hepburn HB, Smith PJ, Potukuchi HK, Lindsay-Scott PJ, Donohoe TJ. Nat. Chem. 2019; 11: 242
- 23d Hepburn HB, Donohoe TJ. Chem. Eur. J. 2020; 26: 1963
- 23e Wu B, Yang J, Hu S.-B, Yu C.-B, Zhao Z.-B, Luo Y, Zhou Y.-G. Sci. China Chem. 2021; 64: 1743
- 24a Vermaak V, Vosloo HC. M, Swarts AJ. Adv. Synth. Catal. 2020; 362: 5788
- 24b Ding F, Zhang Y, Zhao R, Jiang Y, Bao RL.-Y, Lin K, Shi L. Chem. Commun. 2017; 53: 9262
- 24c Li S, Meng W, Du H. Org. Lett. 2017; 19: 2604
- 25a Mao Y, Liu Y, Hu Y, Wang L, Zhang S, Wang W. ACS Catal. 2018; 8: 3016
- 25b Liu Y, Mao Y, Hu Y, Gui J, Wang L, Wang W, Zhang S. Adv. Synth. Catal. 2019; 361: 1554
- 25c Gui J, Cai X, Chen L, Zhou Y, Zhu W, Jiang Y, Hu M, Chen X, Hu Y, Zhang S. Org. Chem. Front. 2021; 8: 4685
- 26 Bose A, Mal P. Chem. Commun. 2017; 53: 11368
- 27 Gujral J, Reddy TP, Gorachand B, Ramachary DB. ChemistrySelect 2018; 3: 7900
- 28 Shen Z, Ni Z, Mo S, Wang J, Zhu Y. Chem. Eur. J. 2012; 18: 4859
- 29 Jin N, Pan C, Zhang H, Xu P, Cheng Y, Zhu C. Adv. Synth. Catal. 2015; 357: 1149
- 30 Neufeldt SR, Seigerman CK, Sanford MS. Org. Lett. 2013; 15: 2302
- 31 Bhattacharyya D, Nandi S, Adhikari P, Sarmah BK, Konwar M, Das A. Org. Biomol. Chem. 2020; 18: 1214
- 32 Xia Y.-T, Sun X.-T, Zhang L, Luo K, Wu L. Chem. Eur. J. 2016; 22: 17151
- 33 Shamsi M, Baradarani MM, Afghan A, Joule JA. ARKIVOC 2011; (ix): 252
- 34 Cadogan JI. G, Hickson CL, Hutchison SH, McNab H. J. Chem. Soc., Perkin Trans. 1 1991; 377
- 35 Pintér Á, Klussmanna M. Adv. Synth. Catal. 2012; 354: 701
