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DOI: 10.1055/s-0041-1737340
Silver-Catalyzed One-Pot Biarylamination of Quinones with Arylamines: Access to N-Arylamine-Functionalized p-Iminoquinone Derivatives
We are grateful for the financial support from the project supported by National College Students Innovation and Entrepreneurship Training Program (Grant No. 202114389016 and 202114389005), the Foundation of Chengdu Normal University Talent Introduction Research Funding (2021YJRC202020), and Chengdu Normal University Project (2021CS21ZCY02).
Abstract
Concise one-pot biarylamination of quinones with arylamines was developed to synthesize N-arylamine-functionalized p-iminoquinones derivatives. The approach employed AgOAc as the catalyst and (NH4)2S2O8 as the oxidant in the presence of 3-chlorophenylboronic acid, giving a series of N-arylamine-functionalized p-iminoquinone derivatives in moderate to good yields whereas reaction in the absence of the 3-chlorophenylboronic acid, gave a series of N-arylamine-functionalized 1,4-naphthoquinone derivatives. This catalytic approach represents a step-economic and convenient strategy for the difunctionalization of quinones.
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Key words
silver-catalyzed - biarylamination - quinones - arylamines - N-arylamine-functionalized p-iminoquinonesQuinone derivatives play significant roles of pharmacological activities in biological systems and exhibit a wide range in developing functional materials, owing to their electron transport properties and unique structure.[1] It is worth noting that iminoquinones are important color dyes[2] and a core structure in some natural products (Figure [1]).[3] Iminoquinones intercalating with DNA[4] are the biological components and key abiotic. Many hybrid materials provided new avenues for molecular sensor,[5] drug delivery,[6] and ligands.[7] Iminoquinones represent the frontier research for the design and generation of molecular complexity.[8] Iminoquinones are usually obtained by oxidation of aniline derivatives.[9] Although, many methods have been used for the synthesis of iminoquinones, these methods require prior synthesis of substrates, multistep reaction procedures, and generally suffer from low yields and poor substrate adaptability and the need for stoichiometric promoters.
There is no general route to access iminoquinone from a single substrate. In recent years, scientific progress in atom-economy and step-economy have been made in the bifunctionalization of the quinone substrate. For example, in 2002, Theodorakis and co-workers reported thioetherification and alkylation of quinones via photochemical decarboxylation of thiocarbonyl derivatives (Scheme [1a]).[10] In 2019, Chen and co-workers developed a copper-catalyzed one-pot three-component thioamination of quinones with amines and thiols (Scheme [1b]).[11] Very recently, in 2021, Wang and co-workers reported a copper-catalyzed one-pot amine-alkylation of quinones with amines and alkanes with DTBP for the first time.[12] From the above reports, it can be seen that one-pot difunctionalization of quinones is rare. Despite the significant progress, the direct biarylamination of quinones with arylamines in a one-pot manner has not yet been reported.
Inspired by these results and our continuous interest in the functionalization of quinones, we herein report a silver-catalyzed one-pot biarylamination of quinones with arylamines toward N-arylamine functionalized p-iminoquinone derivatives from commercially available starting materials using AgOAc as the catalyst and (NH4)2S2O8 as the oxidant in the presence of 3-chlorophenylboronic acid.
The reaction conditions were first optimized by using 1,4-naphthoquinone (1a) and aniline (2a) as the template substrates. As shown in Table [1], the model reaction employed AgOAc (20 mol%) as the catalyst and (NH4)2S2O8 (2.0 equiv) as the oxidant in the presence of 3-chlorophenylboronic acid (1.5 equiv) in DCE (2 mL) as the solvent at 100 °C for 6 hours, giving the desired product of N-arylamine functionalized p-iminoquinone 3a in a yield of 83% (Table [1], entry 1). Subsequently, the effects of different metal catalysts on the reaction were investigated. For instance, AgOTf, Cu(OAc)2, CoCl2, Pd(OAc)2, and FeCl3 were applied as catalysts for the one-pot reaction, respectively (entries 2–6). Among those, AgOAc displayed the highest activity, and the yield of 3a was 83% (entry 1). Next, the oxidant was screened. (NH4)2S2O8 proved to be more efficient than others, such as K2S2O8, Oxone, di-tert-butyl peroxide (DTBP) or tert-butyl peroxybenzoate (TBPB) (entries 7–10). The use of DCE as a solvent was crucial, as the reaction gave poor results in other solvents such as toluene, DCM, DMF, or MeOH (entries 11–14). We further optimized the equivalence of 2a to 3 and 3.5 equivalents, and the reaction yield increased to 93% of 3a (entry 15). Finally, using AgOAc as the catalyst and (NH4)2S2O8 as the oxidant in the absence of the 3-chlorophenylboronic acid, gave the desired product of N-arylamine-functionalized 1,4-naphthoquinone 4a in a yield of 86% (entry 17).
a Reaction conditions: 1,4-naphthoquinone (1a; 0.3 mmol), aniline (2a; mmol), catalyst (20 mol%), oxidant (0.6 mmol, 2.0 equiv), 3-chlorophenylboronic acid (1.5 equiv), solvent (2.0 mL), 100 °C, sealed tube for 6 h.
b Isolated yields; NR = no reaction.
c Reaction carried out in the absence of 3-chlorophenylboronic acid.
Based on the aforementioned optimized conditions, we evaluated the scope of quinones 1 and variously substituted anilines 2 (Scheme [2]).
A variety of substituted anilines were compatible with the Ag-catalyzed biarylamination, regardless of the electronic properties of the anilines affording the products 3a–k. The structure of the N-arylamine-functionalized p-iminoquinone 3a was confirmed by X-ray crystal structure analysis. Notably, the gram-scale synthesis afforded 1.47 g of 3a in 91% yield. Although ortho-monosubstituted aromatic amines are sterically challenging even for biarylamination, the ortho-substituted anilines underwent reactions successfully to give the corresponding aminated products 3l–o. The disubstituted anilines with diverse electronic properties smoothly afforded the desired products 3p–r. The result indicated that aniline with electron-donating substituents exhibited more reactivity than those with electron-withdrawing substituents. Unfortunately, only a trace amount of the desired difunctionalization product was detected when aliphatic amines were used. We have also investigated the substrate scope of quinones. Benzoquinone and anthraquinone was also employed, affording corresponding product 3s and 3t in 71% and 82% yield, respectively.
The approach was employed using AgOAc as the catalyst and (NH4)2S2O8 as the oxidant in the absence of the 3-chlorophenylboronic acid to give N-arylamine-functionalized 1,4-naphthoquinones 4. The reaction scope was next examined by using 1,4-naphthoquinone (1a) with different substituted anilines as a model substrate (Scheme 3). In a 5 mmol scale reaction, 4a could be obtained in 85% yield. Various anilines with steric nature and different electronic were tolerated under the reaction conditions to afford 2-amino-1,4-naphthoquinones 4a–d in moderate to high yields (75–86%).
Naphthylamine was also a suitable reaction partner to give the expected coupling product 4f. Especially, heteroanilines and aliphatic amines were amenable under our reaction conditions and provided the corresponding products 4g, 4h, and 4i in high yields (83–88%). The secondary amine such as morpholine as a substrate showed good reactivity affording the corresponding product 4j in 81% yield.
Control experiments were conducted to clarify the biarylamination reaction pathway (Scheme [4]). The reaction of model compounds 1,4-naphthoquinone (1a) and aniline (2a ) generated the aminated product 4a in 32% yield with (NH4)2S2O8 (Scheme [4a]) and in 43% yield with AgOAc (Scheme [4b]), while the aminated product 4a was obtained in 86% yield with (NH4)2S2O8 and AgOAc (Scheme [4c]), which means that (NH4)2S2O8 and AgOAc can promote the amination reaction. Subsequently, 3a was obtained in 87% yield with the reaction of compound 4a and aniline (2a) under the standard conditions (Scheme [4d]), while 4a was not obtained in the absence of 3-chlorophenylboronic acid (Scheme [4e]). Moreover, 3a was obtained in 89% yield by the reaction of compound 4a and aniline (2a) in the presence of 3-chlorophenylboronic acid (Scheme [4f]). This showed that acid played an important role in this transformation.
On the basis of this and previous reports,[13] a possible reaction mechanism is proposed (Scheme [5]). Initially, the Michael addition of 1,4-naphthoquinone (1a) and aniline (2a) in the presence of AgOAc gives the intermediate A, which is immediately oxidized to intermediate 4a by (NH4)2S2O8. Subsequently, the reaction is probably the Brønsted acid activation of N-arylamine-functionalized 1,4-naphthoquinone (4a) by 3-chlorophenylboronic acid. Finally, the aniline 2a would undergo nucleophilic addition with 4a to give desired product 3a.
In conclusion, we have successfully demonstrated silver-catalyzed one-pot biarylamination of quinones with various arylamines to accomplish the N-arylamine-functionalized p-iminoquinone derivatives. The approach employed AgOAc as the catalyst and (NH4)2S2O8 as the green oxidant in the presence of 3-chlorophenylboronic acid, giving a series of N-arylamine-functionalized p-iminoquinone derivatives in moderate to good yields, whereas reaction in the absence of the 3-chlorophenylboronic acid gave a series of N-arylamine-functionalized 1,4-naphthoquinone derivatives. The significant aspects of our work allow modest functional group tolerance, including electron-donating and electron-withdrawing groups, under the current methodology.
Chemicals and analytical grade solvents were purchased from commercial suppliers and used without further purification unless otherwise stated. All reagents were weighed and handled in air at rt. Analytical TLC was performed on glass plates of Silica Gel GF–254 with detection by UV light (254 and 365 nm). Column chromatography was carried out on silica gel (200-300 mesh). 1H NMR spectra were recorded at 400 MHz and 13C NMR spectra were recorded at 101 MHz by using Agilent 400 MHz NMR spectrometer. Chemical shifts were calibrated using residual undeuterated solvent as an internal reference (1H NMR: CDCl3 7.26 ppm, DMSO-d 6 2.50 ppm, 13C NMR: CDCl3 77.16 ppm, DMSO-d 6 39.52 ppm). Data are reported as follows: chemical shift, multiplicity (standard abbreviations). Coupling constants (J) are reported in hertz (Hz). HRMS were performed on a Thermo Scientific LTQ Orbitrap XL instrument. Melting points were measured with micro melting point apparatus.
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N-Arylamine-Functionalized p-Iminoquinones 3; General Procedure
To a solution of 1,4-naphthoquinone 1 (0.3 mmol), AgOAc (0.06 mmol, 20 mol%), (NH4)2S2O8 (0.6 mmol, 2 equiv), and 3-chlorophenylboronic acid (0.45 mmol, 1.5 equiv) in DCE (2 mL) was added amine 2 (0.9 mmol, 3 equiv). The reaction mixture was stirred at 100 °C for 6 h. After the completion of the reaction (monitored by TLC), the mixture was quenched with brine (2 mL) and extracted with EtOAc (3 × 3 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography to give 3.
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N-Arylamine-Functionalized 1,4-Naphthoquinones 4; General Procedure
To a solution of 1,4-naphthoquinone 1 (0.3 mmol), AgOAc (0.06 mmol, 20 mol%), and (NH4)2S2O8 (0.6 mmol, 2 equiv) in DCE (2 mL) was added amine 2 (0.9 mmol, 3 equiv). The reaction mixture was stirred at 100 °C for 6 h. After the completion of the reaction (monitored by TLC), the mixture was quenched with brine (2 mL) and extracted with EtOAc (3 × 3 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography to give 4.
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(E)-2-(Phenylamino)-4-(phenylimino)naphthalen-1(4H)-one (3a)
Red solid; yield: 88.5 mg (93%); mp 134–136 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.74 (s, 1 H), 8.45 (d, J = 7.8 Hz, 1 H), 8.16 (d, J = 7.6 Hz, 1 H), 7.85 (t, J = 7.5 Hz, 1 H), 7.76 (t, J = 7.4 Hz, 1 H), 7.38 (t, J = 7.8 Hz, 2 H), 7.29–7.22 (m, 4 H), 7.10 (t, J = 7.4 Hz, 1 H), 7.03 (t, J = 7.0 Hz, 1 H), 6.93 (d, J = 7.5 Hz, 2 H), 6.45 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.52, 155.03, 151.29, 141.48, 139.31, 135.32, 134.04, 131.34, 130.60, 129.38, 129.15, 126.38, 125.20, 124.29, 122.58, 121.21, 109.93, 97.11.
HRMS: m/z calcd for C22H17N2O+ (M + H)+: 325.1341; found: 325.1342.
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(E)-2-[(4-Fluorophenyl)amino]-4-[(4-fluorophenyl)imino]naphthalen-1(4H)-one (3b)
Red solid; yield: 68.1 mg (63%); mp 201–203 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.79 (s, 1 H), 8.41 (d, J = 7.8 Hz, 1 H), 8.13 (d, J = 7.4 Hz, 1 H), 7.82 (dd, J = 10.9, 4.2 Hz, 1 H), 7.74 (t, J = 7.5 Hz, 1 H), 7.28–7.12 (m, 6 H), 6.95 (dd, J = 8.6, 5.1 Hz, 2 H), 6.30 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.43, 160.56, 160.14, 158.32, 156.535 (CF, 1 J C,F = 227.3 Hz), 147.51, 142.08, 135.52, 135.29, 134.07, 131.39, 130.55, 126.38, 125.19, 125.07, 124.99, 123.04 (CF, 3 J C,F = 8.1 Hz), 116.18 (CF, 2 J C,F = 22.6 Hz), 115.80.
19F NMR (376 MHz, DMSO-d 6): δ = 118.11, 119.93.
HRMS: m/z calcd for C22H15F2N2O+ (M + H)+: 361.1152; found: 361.1154.
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(E)-2-[(4-Chlorophenyl)amino]-4-[(4-chlorophenyl)imino]naphthalen-1(4H)-one (3c)
Red solid; yield: 76.5 mg (65%); mp 218–220 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.91 (s, 1 H), 8.40 (d, J = 7.8 Hz, 1 H), 8.13 (d, J = 7.7 Hz, 1 H), 7.82 (t, J = 7.6 Hz, 1 H), 7.74 (t, J = 7.5 Hz, 1 H), 7.43 (d, J = 8.5 Hz, 2 H), 7.35 (d, J = 8.7 Hz, 2 H), 7.26 (d, J = 8.7 Hz, 2 H), 6.96 (d, J = 8.4 Hz, 2 H), 6.34 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.32, 155.42, 149.90, 141.56, 138.36, 135.10, 134.17, 131.54, 130.54, 129.36, 129.18, 128.53, 128.05, 126.45, 125.28, 124.21, 123.18, 97.67.
HRMS: m/z calcd for C22H15Cl2N2O+ (M + H)+: 393.0561; found: 393.0564.
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(E)-2-[(4-Bromophenyl)amino]-4-[(4-bromophenyl)imino]naphthalen-1(4H)-one (3d)
Red solid; yield: 99.3 mg (69%); mp 232–235 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.92 (s, 1 H), 8.40 (dd, J = 7.9, 0.9 Hz, 1 H), 8.13 (dd, J = 7.7, 1.1 Hz, 1 H), 7.83 (td, J = 7.7, 1.4 Hz, 1 H), 7.74 (td, J = 7.6, 1.3 Hz, 1 H), 7.59–7.52 (m, 2 H), 7.50–7.43 (m, 2 H), 7.23–7.17 (m, 2 H), 6.93–6.87 (m, 2 H), 6.34 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.32, 155.36, 150.29, 141.46, 138.80, 135.07, 134.15, 132.27, 132.09, 131.54, 130.54, 126.47, 125.29, 124.52, 123.61, 116.71, 116.09.
HRMS: m/z calcd for C22H15Br2N2O+ (M + H)+: 480.9551; found: 480.9552.
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(E)-2-(p-Tolylamino)-4-(p-tolylimino)naphthalen-1(4H)-one (3e)
Red solid; yield: 99.2 mg (94%); mp 175–177 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.60 (s, 1 H), 8.42 (d, J = 7.9 Hz, 1 H), 8.12 (d, J = 7.7 Hz, 1 H), 7.81 (t, J = 7.6 Hz, 1 H), 7.72 (t, J = 7.5 Hz, 1 H), 7.17 (d, J = 7.9 Hz, 2 H), 7.09 (dd, J = 18.4, 8.4 Hz, 4 H), 6.82 (d, J = 8.0 Hz, 2 H), 6.43 (s, 1 H), 2.28 (s, 3 H), 2.22 (s, 3 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.56, 154.70, 148.66, 141.46, 136.72, 135.51, 133.94, 133.47, 133.39, 131.17, 130.52, 129.87, 129.69, 126.30, 125.17, 122.51, 121.40, 109.87, 96.73, 20.87.
HRMS: m/z calcd for C24H21N2O+ (M + H)+: 353.1654; found: 353.1655.
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(E)-2-[(4-Ethylphenyl)amino]-4-[(4-ethylphenyl)imino]naphthalen-1(4H)-one (3f)
Red solid; yield: 108.4 mg (95%); mp 183–185 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.62 (s, 1 H), 8.41 (d, J = 7.2 Hz, 1 H), 8.12 (dd, J = 7.7, 1.0 Hz, 1 H), 7.84–7.78 (m, 1 H), 7.74–7.70 (m, 1 H), 7.19 (d, J = 8.2 Hz, 2 H), 7.09 (q, J = 8.6 Hz, 4 H), 6.82 (d, J = 8.2 Hz, 2 H), 6.38 (s, 1 H), 2.53 (dd, J = 28.4, 7.7 Hz, 4 H), 1.12 (dt, J = 22.5, 7.6 Hz, 6 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.56, 155.05, 149.12, 141.51, 139.89, 139.87, 136.90, 135.41, 133.93, 131.19, 130.58, 128.59, 128.44, 126.31, 125.10, 122.80, 121.41, 96.97, 28.14, 28.00, 16.33, 16.03.
HRMS: m/z calcd for C26H25N2O+ (M + H)+: 381.1967; found: 381.1966.
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(E)-2-[(3-Fluorophenyl)amino]-4-[(3-fluorophenyl)imino]naphthalen-1(4H)-one (3g)
Red solid; yield: 67.0 mg (62%); mp 185–187 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.96 (s, 1 H), 8.39 (d, J = 7.6 Hz, 1 H), 8.13 (d, J = 7.7 Hz, 1 H), 7.83 (t, J = 7.0 Hz, 1 H), 7.75 (t, J = 7.1 Hz, 1 H), 7.38 (dd, J = 14.8, 7.9 Hz, 1 H), 7.27 (dd, J = 15.2, 8.0 Hz, 1 H), 7.08 (d, J = 8.6 Hz, 2 H), 6.92 (t, J = 8.5 Hz, 1 H), 6.88–6.72 (m, 3 H), 6.41 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.27, 164.19, 163.93, 161.76, 161.31, 155.72, 153.33, 141.33 (CF, 3 J C,F = 5.1 Hz), 134.92, 132.95 (CF, 1 J C,F = 259.6 Hz), 130.96, 130.87, 130.71, 130.58, 126.51, 125.28, 118.20, 117.36, 110.89, 110.68, 109.13 (CF, 2 J C,F = 24.2 Hz), 108.21 (CF, 2 J C,F = 23.2 Hz), 98.23.
19F NMR (376 MHz, DMSO-d 6): δ = 112.26, 113.44.
HRMS: m/z calcd for C22H15F2N2O+ (M + H)+: 361.1152; found: 361.1151.
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(E)-2-[(3-Chlorophenyl)amino]-4-[(3-chlorophenyl)imino]naphthalen-1(4H)-one (3h)
Red solid; yield: 75.3 mg (64%); mp 196–198 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.92 (s, 1 H), 8.39 (d, J = 7.7 Hz, 1 H), 8.13 (d, J = 7.6 Hz, 1 H), 7.83 (t, J = 7.5 Hz, 1 H), 7.76 (d, J = 7.5 Hz, 1 H), 7.39 (t, J = 8.0 Hz, 1 H), 7.30–7.12 (m, 4 H), 7.10–6.98 (m, 2 H), 6.90 (d, J = 7.7 Hz, 1 H), 6.36 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.07, 155.83, 152.87, 141.34, 140.99, 134.89, 134.24, 133.92, 131.68, 130.90, 130.84, 130.56, 126.52, 125.30, 124.01, 123.96, 121.96, 120.87, 120.85, 119.95, 98.09.
HRMS: m/z calcd for C22H15Cl2N2O+ (M + H)+: 393.0561; found: 393.0558.
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(E)-2-[(3-Iodophenyl)amino]-4-[(3-iodophenyl)imino]naphthalen-1(4H)-one (3i)
Red solid; yield: 117.5 mg (68%); mp 205–207 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.90 (s, 1 H), 8.40 (d, J = 7.7 Hz, 1 H), 8.13 (d, J = 7.6 Hz, 1 H), 7.78 (dd, J = 26.0, 7.4 Hz, 2 H), 7.43 (d, J = 8.4 Hz, 2 H), 7.35 (d, J = 8.6 Hz, 2 H), 7.25 (d, J = 8.6 Hz, 2 H), 6.96 (d, J = 8.4 Hz, 2 H), 6.33 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.32, 155.54, 149.89, 141.57, 138.34, 135.08, 134.15, 131.47, 130.56, 129.37, 129.18, 128.57, 128.07, 126.46, 125.28, 124.24, 123.19.
HRMS: m/z calcd for C22H15I2N2O+ (M + H)+: 576.9274; found: 576.9276.
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(E)-2-(m-Tolylamino)-4-(m-tolylimino)naphthalen-1(4H)-one (3j)
Red solid, yield: 85.6 mg (81%); mp 145–147 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.62 (s, 1 H), 8.40 (dd, J = 7.8, 0.8 Hz, 1 H), 8.12 (dd, J = 7.7, 1.1 Hz, 1 H), 7.81 (td, J = 7.6, 1.4 Hz, 1 H), 7.72 (td, J = 7.6, 1.3 Hz, 1 H), 7.24 (t, J = 7.6 Hz, 1 H), 7.13 (t, J = 7.7 Hz, 1 H), 7.02 (d, J = 9.3 Hz, 2 H), 6.90 (d, J = 7.5 Hz, 1 H), 6.82 (d, J = 7.5 Hz, 1 H), 6.73–6.67 (m, 2 H), 6.44 (s, 1 H), 2.30 (s, 3 H), 2.19 (s, 3 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.50, 154.94, 151.45, 141.22, 139.26, 138.69, 138.54, 135.29, 134.01, 131.28, 130.56, 129.23, 128.93, 126.36, 125.14, 124.90, 124.88, 122.64, 121.69, 119.82, 118.26, 97.28, 21.46.
HRMS: m/z calcd for C24H21N2O+ (M + H)+: 353.1654; found: 353.1655.
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(E)-2-[(3-Methoxyphenyl)amino]-4-[(3-methoxyphenyl)imino]naphthalen-1(4H)-one (3k)
Red solid; yield: 95.7 mg (83%); mp 141–143 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.42 (d, J = 7.8 Hz, 1 H), 8.12 (d, J = 7.6 Hz, 1 H), 7.99 (s, 1 H), 7.83 (t, J = 7.6 Hz, 1 H), 7.74 (t, J = 7.5 Hz, 1 H), 7.03 (dt, J = 14.4, 7.6 Hz, 5 H), 6.93 (t, J = 7.3 Hz, 1 H), 6.82 (d, J = 7.5 Hz, 1 H), 6.74 (d, J = 7.6 Hz, 1 H), 5.98 (s, 1 H), 3.74 (s, 3 H), 3.67 (s, 3 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.43, 155.47, 151.94, 149.65, 140.27, 140.18, 135.37, 134.17, 131.33, 130.23, 127.38, 126.38, 125.86, 125.46, 125.37, 122.49, 121.45, 120.84, 112.29, 112.25, 97.91, 56.01, 55.81.
HRMS: m/z calcd for C24H21N2O3 + (M + H)+: 385.1552; found: 385.1554.
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(E)-2-[(2-Fluorophenyl)amino]-4-[(2-fluorophenyl)imino]naphthalen-1(4H)-one (3l)
Red solid; yield: 64.8 mg (60%); mp 162–164 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.73 (s, 1 H), 8.42 (dd, J = 7.8, 0.8 Hz, 1 H), 8.14 (dd, J = 7.7, 1.1 Hz, 1 H), 7.85 (td, J = 7.6, 1.4 Hz, 1 H), 7.77 (td, J = 7.6, 1.3 Hz, 1 H), 7.28 (t, J = 7.8 Hz, 1 H), 7.23–7.04 (m, 6 H), 6.91 (td, J = 8.1, 1.8 Hz, 1 H), 5.74 (dd, J = 3.0, 1.6 Hz, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.01, 157.41, 156.83, 154.92, 153.71, 142.49, 138.46, 134.91, 133.00 (CF, 1 J C,F = 263.6 Hz), 130.37, 127.73 (CF, 3 J C,F = 9.1 Hz), 127.30, 126.52, 125.60 (CF, 2 J C,F = 19.2 Hz), 125.29, 124.89, 123.18, 116.76, 116.61, 116.13, 116.07, 97.23.
19F NMR (376 MHz, DMSO-d 6): δ = –119.30, –126.14.
HRMS: m/z calcd for C22H15F2N2O+ (M + H)+: 361.1152 found: 361.1153.
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(E)-2-[(2-Chlorophenyl)amino]-4-[(2-chlorophenyl)imino]naphthalen-1(4H)-one (3m)
Red solid; yield: 72.9 mg (62%); mp 171–173 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.57 (s, 1 H), 8.44 (d, J = 7.6 Hz, 1 H), 8.15 (d, J = 7.7 Hz, 1 H), 7.85 (dd, J = 10.9, 4.3 Hz, 1 H), 7.77 (t, J = 7.1 Hz, 1 H), 7.44 (dd, J = 12.2, 8.6 Hz, 2 H), 7.26 (dd, J = 13.3, 6.8 Hz, 3 H), 7.17 (dd, J = 10.6, 4.2 Hz, 1 H), 7.05 (t, J = 7.1 Hz, 1 H), 6.90–6.86 (m, 1 H), 5.63 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 180.99, 156.04, 147.91, 142.16, 135.66, 134.92, 134.42, 131.79, 130.57, 130.39, 129.98, 129.37, 128.36, 127.73, 127.68, 127.00, 126.54, 125.52, 124.65, 122.06, 97.36.
HRMS: m/z calcd for C22H15Cl2N2O+ (M + H)+: 393.0561; found: 393.0558.
#
(E)-2-[(2-Bromophenyl)amino]-4-[(2-bromophenyl)imino]naphthalen-1(4H)-one (3n)
Red solid; yield: 87.8 mg (61%); mp 176–178 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.83 (s, 1 H), 8.39 (d, J = 7.5 Hz, 1 H), 8.12 (d, J = 7.3 Hz, 1 H), 7.84–7.71 (m, 2 H), 7.44–7.21 (m, 6 H), 6.94 (d, J = 8.0 Hz, 2 H), 6.33 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.29, 155.40, 149.89, 141.54, 138.35, 135.05, 134.13, 131.50, 130.52, 129.35, 129.16, 128.54, 127.83, 126.43, 125.27, 124.19, 123.16, 97.36.
HRMS: m/z calcd for C22H15Br2N2O+ (M + H)+: 480.9551; found: 480.9547.
#
(E)-2-[(2-Methoxyphenyl)amino]-4-[(2-methoxyphenyl)imino]naphthalen-1(4H)-one (3o)
Red solid; yield: 85.3 mg (74%); mp 131–133 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.42 (d, J = 7.1 Hz, 1 H), 8.12 (dd, J = 7.7, 1.1 Hz, 1 H), 8.00 (s, 1 H), 7.83 (td, J = 7.6, 1.3 Hz, 1 H), 7.77–7.72 (m, 1 H), 7.10–6.98 (m, 5 H), 6.95–6.91 (m, 1 H), 6.85–6.80 (m, 1 H), 6.74 (dd, J = 7.6, 1.5 Hz, 1 H), 5.98 (s, 1 H), 3.74 (s, 3 H), 3.67 (s, 3 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.43, 155.46, 151.95, 149.65, 140.27, 140.18, 135.20, 134.17, 131.24, 130.24, 127.38, 126.38, 125.86, 125.49, 125.46, 122.51, 121.45, 120.84, 112.25, 55.88.
HRMS: m/z calcd for C24H21N2O3 + (M + H)+: 385.1552; found: 385.1553.
#
(E)-2-[(2,4-Difluorophenyl)amino]-4-[(2,4-difluorophenyl)imino]naphthalen-1(4H)-one (3p)
Red solid; yield: 60.6 mg (51%); mp 213–215 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.74 (s, 1 H), 8.43–8.37 (m, 1 H), 8.12 (dd, J = 7.7, 1.1 Hz, 1 H), 7.83–7.71 (m, 2 H), 7.39–7.21 (m, 3 H), 7.11–7.01 (m, 2 H), 6.94 (td, J = 9.0, 6.2 Hz, 1 H), 5.63 (dd, J = 2.7, 1.7 Hz, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 180.89, 159.12, 157.89, 157.25, 155.26, 153.67, 151.09, 142.94, 141.56, 135.04, 134.87, 132.99 (CF, 1 J C,F = 250.6 Hz) 130.32, 128.99, 126.48, 125.46, 123.90 (CF, 3 J C,F = 6.1 Hz), 122.91, 112.40 (CF, 2 J C,F = 20.0 Hz) 111.86, 111.65, 105.24, 104.66 (CF, 2 J C,F = 26.3 Hz), 96.82.
19F NMR (376 MHz, DMSO-d 6): δ = 112.36, 114.52, 116.11, 120.91.
HRMS: m/z calcd for C22H13F4N2O+ (M + H)+: 397.0964; found: 397.0966.
#
(E)-2-[(3,5-Dimethylphenyl)amino]-4-[(3,5-dimethylphenyl)imino]naphthalen-1(4H)-one (3q)
Red solid; yield: 100.4 mg (88%); mp 162–164 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.45–8.35 (m, 2 H), 8.12 (d, J = 7.7 Hz, 1 H), 7.80 (t, J = 7.4 Hz, 1 H), 7.72 (t, J = 7.4 Hz, 1 H), 6.80 (s, 2 H), 6.72 (s, 1 H), 6.65 (s, 1 H), 6.45 (d, J = 23.8 Hz, 3 H), 2.27 (d, J = 12.7 Hz, 6 H), 2.15 (s, 6 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.51, 154.82, 151.67, 141.15, 139.16, 138.56, 138.31, 135.30, 134.01, 131.24, 130.45, 126.34, 125.78, 125.53, 125.14, 120.01, 118.39, 97.14, 21.46, 21.33.
HRMS: m/z calcd for C26H25N2O+ (M + H)+: 381.1967; found: 381.1969.
#
(E)-2-[(2,4-Dimethylphenyl)amino]-4-[(2,4-dimethylphenyl)imino]naphthalen-1(4H)-one (3r)
Red solid; yield: 94.7 mg (83%); mp 155–157 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.46 (d, J = 7.8 Hz, 1 H), 8.18 (s, 1 H), 8.13 (d, J = 7.7 Hz, 1 H), 7.80 (t, J = 7.6 Hz, 1 H), 7.72 (t, J = 7.5 Hz, 1 H), 7.03–6.94 (m, 3 H), 6.93–6.85 (m, 2 H), 6.50 (d, J = 7.8 Hz, 1 H), 5.67 (s, 1 H), 2.19 (d, J = 1.6 Hz, 6 H), 2.07 (s, 3 H), 1.99 (s, 3 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.51, 154.04, 147.18, 142.94, 135.71, 135.53, 134.53, 133.93, 133.88, 133.04, 131.81, 131.24, 131.05, 130.46, 128.87, 127.44, 126.70, 126.19, 125.87, 125.24, 119.71, 95.71, 20.90, 18.08, 17.84.
HRMS: m/z calcd for C26H25N2O+ (M + H)+: 381.1967; found: 381.1963.
#
(Z)-2-(Phenylamino)-4-(phenylimino)cyclohexa-2,5-dien-1-one (3s)
Red solid; yield: 58.4 mg (71%); mp 125–127 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 9.23 (s, 1 H), 8.56 (s, 1 H), 7.41 (d, J = 5.3 Hz, 3 H), 7.22–7.09 (m, 4 H), 6.98 (dd, J = 17.0, 5.9 Hz, 3 H), 5.94 (s, 1 H), 5.85 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 180.59, 154.25, 150.26, 150.02, 141.70, 139.24, 138.72, 129.75, 129.38, 129.28, 125.67, 124.68, 124.36, 122.47, 121.21, 120.06, 97.10, 90.54.
HRMS: m/z calcd for C18H15N2O+ (M + H)+: 275.1184; found: 275.1191.
#
(E)-2-(Phenylamino)-4-(phenylimino)anthracen-1(4H)-one (3t)
Red solid; yield: 92.0 mg (82%); mp 230–232 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.99 (s, 1 H), 8.82 (d, J = 7.5 Hz, 2 H), 8.26 (dd, J = 17.6, 7.9 Hz, 2 H), 7.75–7.67 (m, 2 H), 7.37 (t, J = 7.8 Hz, 2 H), 7.29–7.21 (m, 4 H), 7.10–7.00 (m, 2 H), 6.95 (d, J = 7.3 Hz, 2 H), 6.55 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.32, 154.89, 151.42, 142.21, 139.28, 135.19, 133.46, 131.16, 130.31, 129.75, 129.39, 129.19, 128.57, 128.49, 128.10, 125.46, 124.34, 124.00, 122.69, 121.36, 109.99, 98.87.
HRMS: m/z calcd for C26H19N2O+ (M + H)+: 375.1497; found: 375.1497.
#
2-(Phenylamino)naphthalene-1,4-dione (4a)[14]
Red solid; yield: 64.3 mg (86%); mp 185–187 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 9.21 (s, 1 H), 8.03 (d, J = 7.5 Hz, 1 H), 7.92 (d, J = 7.5 Hz, 1 H), 7.83 (t, J = 7.0 Hz, 1 H), 7.75 (t, J = 7.0 Hz, 1 H), 7.45–7.33 (m, 4 H), 7.20 (t, J = 7.2 Hz, 1 H), 6.08 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 183.01, 181.99, 146.61, 138.48, 135.32, 133.06, 132.99, 130.84, 129.73, 126.55, 125.70, 124.13, 102.35.
#
2-[(3-Methoxyphenyl)amino]naphthalene-1,4-dione (4b)[13b]
Red solid; yield: 70.3 mg (84%); mp 162–164 °C.
1H NMR (400 MHz, CDCl3): δ = 8.11 (ddd, J = 7.5, 4.2, 1.1 Hz, 2 H), 7.78–7.74 (m, 1 H), 7.66 (dd, J = 7.6, 6.3 Hz, 1 H), 7.55 (s, 1 H), 7.31 (t, J = 8.1 Hz, 1 H), 6.87 (dd, J = 7.9, 1.8 Hz, 1 H), 6.80 (t, J = 2.2 Hz, 1 H), 6.75 (dd, J = 8.3, 2.3 Hz, 1 H), 6.45 (s, 1 H), 3.82 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 183.92, 182.01, 160.60, 144.55, 138.59, 134.90, 133.17, 132.34, 130.44, 130.32, 126.52, 126.15, 114.75, 110.97, 108.46, 103.80, 55.43.
#
2-[(3-Chlorophenyl)amino]naphthalene-1,4-dione (4c)[15]
Red solid; yield: 63.7 mg (75%); mp 156–158 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 9.25 (s, 1 H), 8.04 (d, J = 7.4 Hz, 1 H), 7.94 (d, J = 7.4 Hz, 1 H), 7.82 (t, J = 7.3 Hz, 1 H), 7.75 (t, J = 7.3 Hz, 1 H), 7.42 (t, J = 7.9 Hz, 2 H), 7.35 (d, J = 8.0 Hz, 1 H), 7.21 (d, J = 7.8 Hz, 1 H), 6.16 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 183.29, 181.54, 145.93, 140.26, 135.22, 133.07, 131.16, 130.29, 126.54, 125.73, 125.14, 124.58, 123.53, 122.14, 103.56, 79.68, 79.35, 79.02.
#
2-(o-Tolylamino)naphthalene-1,4-dione (4d)[16]
Red solid; yield: 61.6 mg (78%); mp 143–145 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 8.98 (s, 1 H), 8.00 (dd, J = 7.6, 0.9 Hz, 1 H), 7.88 (dd, J = 7.6, 0.9 Hz, 1 H), 7.79 (td, J = 7.5, 1.3 Hz, 1 H), 7.71 (td, J = 7.5, 1.3 Hz, 1 H), 7.32 (d, J = 7.1 Hz, 1 H), 7.28–7.18 (m, 3 H), 5.31 (s, 1 H), 2.18 (s, 3 H).
13C NMR (101 MHz, DMSO-d 6): δ = 182.47, 181.84, 148.13, 136.55, 135.23, 134.96, 133.20, 132.84, 131.46, 130.85, 127.58, 127.31, 127.18, 126.40, 125.72, 101.72, 17.85.
#
2-(Naphthalen-1-ylamino)naphthalene-1,4-dione (4e)[15]
Red solid; yield: 69.1 mg (77%); mp 156–158 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 9.50 (s, 1 H), 8.08 (dd, J = 7.5, 1.1 Hz, 1 H), 8.03–7.98 (m, 1 H), 7.94 (d, J = 8.2 Hz, 1 H), 7.92–7.86 (m, 2 H), 7.79 (dtd, J = 21.3, 7.4, 1.4 Hz, 2 H), 7.61–7.48 (m, 4 H), 5.22 (s, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 182.57, 181.79, 149.31, 135.21, 134.47, 134.33, 133.17, 132.96, 131.02, 129.35, 128.84, 127.95, 127.06, 127.00, 126.49, 126.37, 125.73, 125.03, 123.63, 102.60.
#
2-(Pyridin-2-ylamino)naphthalene-1,4-dione (4f)[17]
Red solid; yield: 53.3 mg (71%); mp 203–205 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 9.45 (s, 1 H), 8.38 (dd, J = 4.8, 1.2 Hz, 1 H), 8.07–8.03 (m, 1 H), 7.94 (d, J = 7.4 Hz, 1 H), 7.88–7.70 (m, 4 H), 7.56 (s, 1 H), 7.03 (dd, J = 6.7, 5.2 Hz, 1 H).
13C NMR (101 MHz, DMSO-d 6): δ = 184.73, 181.84, 154.22, 147.73, 143.13, 138.30, 135.23, 133.40, 132.46, 130.80, 126.70, 125.69, 118.47, 115.68, 110.51.
#
2-(Cyclohexylamino)naphthalene-1,4-dione (4g)[17]
Red solid; yield: 67.4 mg (88%); mp 103–105 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 7.92 (ddd, J = 12.4, 7.6, 0.9 Hz, 2 H), 7.78 (td, J = 7.5, 1.3 Hz, 1 H), 7.68 (td, J = 7.5, 1.3 Hz, 1 H), 7.04 (d, J = 8.4 Hz, 1 H), 5.70 (s, 1 H), 1.83 (d, J = 8.5 Hz, 2 H), 1.68 (dd, J = 8.4, 3.0 Hz, 2 H), 1.57 (d, J = 12.7 Hz, 1 H), 1.53–1.20 (m, 5 H), 1.15 (ddd, J = 29.9, 23.9, 15.2 Hz, 2 H).
13C NMR (101 MHz, DMSO-d 6): δ = 182.12, 181.72, 147.67, 135.23, 133.54, 132.51, 130.81, 126.28, 125.69, 99.88, 51.20, 31.48, 25.56, 24.88.
#
2-(Ethylamino)naphthalene-1,4-dione (4h)[18]
Red solid; yield: 50.1 mg (83%); mp 146–148 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 7.94 (ddd, J = 14.7, 7.6, 0.8 Hz, 2 H), 7.82–7.78 (m, 1 H), 7.72–7.68 (m, 1 H), 7.50 (s, 1 H), 5.64 (s, 1 H), 3.22–3.16 (m, 2 H), 1.15 (t, J = 7.2 Hz, 3 H).
13C NMR (101 MHz, DMSO-d 6): δ = 182.05, 181.65, 148.77, 135.25, 133.65, 132.54, 130.84, 126.30, 125.75, 99.61, 37.09, 13.42.
#
2-(Propylamino)naphthalene-1,4-dione (4i)[19]
Red solid; yield: 54.8 mg (85%); mp 167–169 °C.
1H NMR (400 MHz, DMSO-d 6): δ = 7.93 (dd, J = 15.0, 7.6 Hz, 2 H), 7.80 (dd, J = 10.7, 4.3 Hz, 1 H), 7.72–7.66 (m, 1 H), 7.54 (t, J = 5.8 Hz, 1 H), 5.64 (s, 1 H), 3.11 (dd, J = 13.9, 6.6 Hz, 2 H), 1.57 (dd, J = 14.5, 7.3 Hz, 2 H), 0.88 (t, J = 7.4 Hz, 3 H).
13C NMR (101 MHz, DMSO-d 6): δ = 181.72, 181.63, 148.99, 135.24, 132.52, 132.25, 130.35, 126.30, 125.73, 99.62, 21.14, 11.84.
#
2-Morpholinonaphthalene-1,4-dione (4j)[20]
Yellow solid; yield: 59.0 mg (81%); mp 155–157 °C.
1H NMR (400 MHz, CDCl3): δ = 8.01 (dd, J = 15.0, 7.5 Hz, 2 H), 7.67 (dt, J = 22.0, 7.4 Hz, 2 H), 6.01 (s, 1 H), 3.89–3.83 (m, 4 H), 3.53–3.46 (m, 4 H).
13C NMR (101 MHz, CDCl3): δ = 183.73, 182.82, 153.62, 133.95, 132.68, 132.60, 132.19, 126.70, 125.59, 111.94, 66.41, 49.14.
#
#
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/s-0041-1737340.
- Supporting Information
-
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Corresponding Authors
Publication History
Received: 02 November 2021
Accepted after revision: 16 December 2021
Article published online:
07 February 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
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-
References
- 1a Klare JE, Tulevski GS, Sugo K, De Picciotto A, White KA, Nuckolls C. J. Am. Chem. Soc. 2003; 125: 6030
- 1b Nowicka B, Kruk J. Biochim. Biophys. Acta. 2010; 1797: 1587
- 1c Petrangolini P, Alessandrini A, Facci P. J. Phys. Chem. C. 2013; 117: 17451
- 2a Adachi M, Murata Y, Nakamura S. J. Org. Chem. 1993; 58: 5238
- 2b Tao W, Barra M. J. Org. Chem. 2001; 66: 2158
- 2c Barra M, Tan A, Wong S. Dyes Pigm. 2004; 61: 63
- 2d Vittum PW, Brown GH. J. Am. Chem. Soc. 1946; 68: 2235
- 2e Josephy PD, Mason RP, Eling T. Carcinogenesis. 1982; 3: 1227
- 3a Imai S, Shimazu A, Furihata K, Furihata K, Hayakawa Y, Seto H. J. Antibiot. 1990; 43: 1606
- 3b Imai S, Noguchi T, Seto H. J. Antibiot. 1993; 46: 1232
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