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DOI: 10.1055/s-0033-1340466
Mild and Efficient One-Pot Synthesis of Diverse Flavanone Derivatives via an Organocatalyzed Mannich-Type Reaction
Publication History
Received: 26 October 2013
Accepted after revision: 25 November 2013
Publication Date:
16 December 2013 (online)
Abstract
A facile ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of biologically interesting flavanone derivatives from 2-hydroxyacetophenones, aromatic aldehydes, and aniline via a Mannich-type reaction is described. This synthetic method provides a rapid access to biologically interesting flavanone derivatives. To demonstrate this method, several biologically interesting natural products bearing a flavanone moiety were synthesized as racemates.
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Flavanones (chroman-4-ones) are an abundant subclass of flavonoids, which are widely distributed in nature as racemates and chiral forms (Figure [1]).[1] Flavanones have received considerable attention due to their favorable pharmacological properties, which include antioxidant, antitumor, antileukemia, anti-allergic, antiproliferative, cytoprotective, antifungal, and antibacterial activities.[2] They also display important biological activities as tyrosinase[3] and aldose reductase inhibitors,[4] and as nonsteroidal inhibitors of human aromatase.[5] The flavanones also serve as important intermediates or precursors in the syntheses of many biologically active natural products.[6] Among these, 7-methoxyflavanone (1) and 4′,7-dimethoxyflavanone (2), isolated from Ixeridium gracile [7] and Terminalia fagifolia,[8] respectively, exhibited potent antiproliferative, anticarcinogenic, anticancer, antioxidative, and antituberculosis activities.[9] 5,7-Dimethoxyflavanone (3), pinostrobin (4) (5-hydroxy-7-methoxyflavanone), and 5-hydroxy-4′,7-dimethoxyflavanone (5) (4′,7-di-O-methylnaringenin) were isolated from Piper methylsticum [10] and Combretaceae apiculatum,[11] Miliusa sinensis,[12] Piper porphyrophyllum,[13] Chloranthus elatior,[14] and Otochilus fuscus.[15] These compounds exhibited antimicrobial, antibacterial, antifungal, antiviral, aniplasmodial, antioxidant, anticancer, and anti-inflammatory activities.[16]
Pinocembrin (6) was isolated from Penicillium italicum,[17] Combretum apiculatum,[18] and Boesenbergia pandurata,[19] and found to exhibit antifungal, antioxidant, antibacterial, antimicrobial, anti-adhesion, antituberculosis, anti-aggregatory, anti-inflammatory, and antitumor activities.[20] Strobopinin (7) and its isomer cryptostrobin (8) were isolated from Melaleuca quinquenervia,[21] and they displayed antioxidant, antimalarial, antifungal, antimycobacterial, anti-inflammatory, antitumoral, and antiplasmodial activities.[22] In addition, they were found to inhibit novel influenza A(H1N1)[23] and P2Y2 receptor antagonists[24] and to have immunomodulatory effects.[25]
The general method used to synthesize flavanones involves the cyclization of the appropriately substituted 2-hydroxychalcones, prepared by aldol condensation between 2-hydroxyacetophenones and aldehydes. This cyclization has been carried out under several conditions using acids,[26] bases,[27] photochemical,[28] and electrochemical reactions.[29] Other alternative approaches to the syntheses of flavanones include the oxidation of flavan-4-ol,[30] the transformation of phenylalkenyl aryl ethers in the presence of Hg(OCOCF3)2,[31] the intramolecular oxa-Michael addition of activated α,β-unsaturated ketones,[32] Julia–Kocienski olefination of 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethanones with aldehydes in the presence of a base,[33] intermolecular C–O addition of carboxylic acids to arynes,[34] and intramolecular dehydration of 3-hydroxy-1-(2-hydroxyphenyl)-3-arylpropan-1-ones.[35]
Although a number of methods have been reported for the synthesis of flavanone derivatives, there is still a need for generally applicable, facile synthetic methods that can produce various flavanone derivatives using milder catalysts. Recently, Yao et al. reported the synthesis of flavanone derivatives under mild reaction conditions using an iodine-catalyzed Mannich-type reaction.[36] This reaction is important for carbon–carbon bond formation, and a valuable tool for constructing a diverse array of pharmaceutically useful natural and synthetic products.[37] We report herein a mild, facile one-pot synthesis of a variety of biologically interesting diverse flavanone derivatives using ethylenediamine diacetate (EDDA) as a mild organocatalyst (Scheme [1]).
Organocatalysts act as efficient and convenient catalysts for a variety of synthetically useful reactions.[38] In a previous study, we described a new method for synthesizing a variety of benzopyrans using EDDA as effective organocatalysts.[39] As part of our ongoing study into the synthetic efficiency of EDDA as a catalyst for the development of novel organic reactions, we have now examined the EDDA-catalyzed reactions of 2-hydroxyacetophenones with aldehydes and aniline to afford flavanone derivatives via a Mannich-type reaction.
Initially, the reaction of 2-hydroxyacetophenone (9a) (1.0 mmol) with benzaldehyde (10a) (1.2 mmol) and aniline (11) (1.2 mmol) was examined in the presence of several catalysts (20 mol%), namely, ceric(IV) ammonium nitrate (CAN), InCl3, In(OTf)3, Yb(OTf)3, RhCl2(PPh3)3, EDDA, or other ammonium and pyridinium salts in different solvents (Table [1]). The best yield (82%) was obtained in the presence of 20 mol% of EDDA at 40 °C for 12 hours in MeOH (Table [1], entry 10). Importantly, EDDA showed superiority to other ammonium and pyridinium salts, such as ethylenediamine dihydrochloride, ammonium acetate, piperidine hydrochloride, pyridine hydrochloride, and pyridinium p-toluenesulfonate (PPTS) in terms of yields (entries 12–16). The synthesized compound 12a was identified by analyzing the spectral data in comparison with the reported data.[36] Interestingly, the reaction of 9a and benzaldehyde (10a) in the absence of aniline in 20 mol% of EDDA at 40 °C for 24 hours did not produce the desired product.
To explore the generality of this transformation, additional reactions of several 2-hydroxyacetophenones 9a–c with aniline (11) and aromatic aldehydes 10a–j bearing electron-donating and electron-withdrawing groups on the benzene ring were conducted under optimized reaction conditions. The results obtained are summarized in Table [2].
The reaction of 2-hydroxyacetophenone (9a) with aniline and 3-methoxybenzaldehyde (10b) or 2,5-dimethylbenzaldehyde (10c) in the presence of 20 mol% of EDDA at 40 °C for 12 hours in methanol produced the desired products 12b (79%) and 12c (69%), respectively (Table [2], entries 1, 2). Treatment of 9a with 4-bromobenzaldehyde (10d) or 4-chlorobenzaldehyde (10e) afforded the cycloadducts 12d and 12e in 74 and 80% yield, respectively (entries 3, 4). Reaction with 2-naphthaldeyde (10f) or 5-methylfurfural (10g) produced the desired cycloadducts 12f and 12g in 71 and 60% yield, respectively (entries 5, 6). Similarly, reactions of 2-hydroxy-5-methylacetophenone (9b) with aniline and aromatic aldehydes afforded the products 12h–o in 52–87% yields (entries 7–14). Finally, reactions of 2-hydroxy-4-methoxyacetophenone (9c) with aromatic aldehydes 10b,d–f produced 12p–s in 61–72% yields (entries 15–18).
a The reaction was carried out using 9 (1.0 mmol), 10 (1.2 mmol), aniline (11; 1.2 mmol), and EDDA catalyst (0.2 mmol) in a MeOH (2.0 mL) at 40 °C.
b Isolated yield.
The formation of 12a can be explained by the mechanism proposed in Scheme [2]. The carbonyl group of benzaldehyde (10a) could be protonated by EDDA, which could facilitate the formation of an iminium ion 14. The enol form 15, generated from 2-hydroxyacetophenone (9a), in the presence of EDDA, could attack the iminium ion 14 to give intermediate 16, which could undergo cycloaddition to form the flavanone 12a via an intramolecular SN2 reaction. Importantly, when aniline was not used, the reaction did not proceed. This suggests no pathway via a direct aldol reaction followed by next 1,4-Michael-type cycloaddition of the hydroxyl group to give product 12a.
As an application of this method, one-step synthesis of naturally occurring 7-methoxyflavanone (1) 4′,7-dimethoxyflavanone (2), and 5,7-dimethoxyflavanone (3) as racemates was conducted as shown in Scheme [3]. Reaction of 9c with benzaldehyde (10a) and aniline (11) in the presence of 20 mol% of EDDA at 40 °C for 12 hours in methanol provided 7-methoxyflavanone (1) in 62% yield, whereas reaction with 4-methoxybenzaldehyde (10h) afforded 4′,7-dimethoxyflavanone (2) in 59% yield. Similarly, treatment of 9d with benzaldehyde (10a) and aniline (11) in the presence of 20 mol% of EDDA at 40 °C for 12 hours in methanol afforded 5,7-dimethoxyflavanone (3) in 55% yield. The spectral data of synthesized compounds 1–3 concurred well with the reported values.[7] [8] [11]
In summary, an efficient one-pot synthesis of biologically interesting flavanone derivatives from reactions of 2-hydroxyacetophenones with aromatic aldehydes and aniline using EDDA as an organocatalyst is described. This method has the advantages of mild reaction conditions, use of an inexpensive nonmetal catalyst, simple experimentation requirements, and good yields. Furthermore, this method was used to synthesize the naturally occurring materials, 7-methoxyflavanone (1), 4′,7-dimethoxyflavanone (2), and 5,7-dimethoxyflavanone (3).
All the experiments were carried out under N2 atmosphere. Merck precoated silica gel plates (Art. 5554) with a fluorescent indicator were used for analytical TLC. Flash column chromatography was performed using silica gel 9385 (Merck). 1H NMR and 13C NMR spectra were recorded on a Bruker Model ARX (300 and 75 MHz, respectively) spectrometer in CDCl3 as the solvent. IR spectra were recorded on a Jasco FTIR 5300 spectrophotometer. Melting point was measured with a Fisher-Johns melting point apparatus and are uncorrected. HRMS were carried out at the Korea Basic Science Institute.
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Flavanone Derivatives; General Procedure
To a solution of 2-hydroxyacetophenone 9 (1.0 mmol), aldehyde 10 (1.2 mmol), and aniline (11; 112 mg, 1.2 mmol) in MeOH (2 mL) was added EDDA (20 mol%) and the reaction mixture was heated at 40 °C for 12–15 h under N2 atmosphere. After completion of the reaction, solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel with EtOAc–hexane gradient as eluent to give the desired pure product.
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2-Phenylchroman-4-one (12a)
Yield: 184 mg (82%); colorless solid; mp 107–108 °C.
IR (KBr): 3064, 2899, 1689, 1605, 1462, 1303, 1225, 1147, 1110, 1064, 974, 904 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.93 (dd, J = 8.1, 1.5 Hz, 1 H), 7.52–7.37 (m, 6 H), 7.06–7.02 (m, 2 H), 5.49 (dd, J = 13.2, 3.0 Hz, 1 H), 3.09 (dd, J = 16.8, 13.2 Hz, 1 H), 2.90 (dd, J = 16.8, 3.0 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 191.9, 161.5, 138.7, 136.1, 128.8, 128.7, 127.0, 126.1, 121.6, 120.9, 118.1, 79.5, 44.6.
HRMS (EI): m/z calcd for C15H12O2: 224.0837; found: 224.0835.
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2-(3-Methoxyphenyl)chroman-4-one (12b)
Yield: 201 mg (79%); colorless solid; mp 111–113 °C.
IR (KBr): 3058, 2891, 1691, 1602, 1576, 1461, 1371, 1303, 1226, 907 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.93 (dd, J = 7.5, 0.9 Hz, 1 H), 7.52–7.46 (m, 1 H), 7.36–7.30 (m, 1 H), 7.06–7.02 (m, 4 H), 6.92–6.88 (m, 1 H), 5.46 (dd, J = 13.2, 2.7 Hz, 1 H), 3.83 (s, 3 H), 3.07 (dd, J = 16.8, 13.2 Hz, 1 H), 2.84 (dd, J = 16.8, 3.0 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 192.0, 161.6, 160.1, 140.4, 136.3, 130.1, 127.2, 121.8, 121.1, 118.5, 118.3, 114.2, 112.0, 79.6, 55.4, 44.8.
HRMS (EI): m/z calcd for C16H14O3: 254.0943; found: 254.0942.
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2-(2,5-Dimethylphenyl)chroman-4-one (12c)
Yield: 174 mg (69%) ; colorless solid; mp 102–104 °C.
IR (KBr): 3022, 2911, 1696, 1605, 1461, 1374, 1305, 1064, 880 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.83 (dd, J = 8.1, 1.8 Hz, 1 H), 7.35 (td, J = 8.4, 1.8 Hz, 1 H), 7.28 (s, 1 H), 6.98 (s, 2 H), 6.96–6.88 (m, 2 H), 5.52 (dd, J = 13.8, 2.7 Hz, 1 H), 2.92 (dd, J = 17.1, 13.8 Hz, 1 H), 2.69 (dd, J = 17.1, 2.7 Hz, 1 H), 2.24 (s, 3 H), 2.19 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 192.2, 161.9, 136.6, 136.1, 136.1, 131.9, 130.8, 129.3, 127.2, 126.4, 121.6, 121.0, 118.1, 77.6, 43.7, 21.2, 18.6.
HRMS (EI): m/z calcd for C17H16O2: 252.1150; found: 252.1149.
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2-(4-Bromophenyl)chroman-4-one (12d)
Yield: 223 mg (74%); colorless solid; mp 114–115 °C.
IR (KBr): 2930, 1685, 1566, 1465, 1300, 1230, 1050, 906 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.80 (dd, J = 8.1, 1.5 Hz, 1 H), 7.43–7.34 (m, 3 H), 7.21 (d, J = 8.4 Hz, 2 H), 6.94–6.90 (m, 2 H), 5.31 (dd, J = 12.6, 3.0 Hz, 1 H), 2.88 (dd, J = 16.5, 12.9 Hz, 1 H), 2.75 (dd, J = 16.8, 3.0 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 191.5, 161.1, 137.6, 136.0, 131.8, 127.6, 126.9, 122.5, 121.6, 120.7, 117.9, 78.6, 44.3.
HRMS (EI): m/z calcd for C15H11BrO2: 301.9942; found: 301.9940.
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2-(4-Cholophenyl)chroman-4-one (12e)
Yield: 206 mg (80%); colorless solid; mp 92–94 °C.
IR (KBr): 2988, 1685, 1462, 1374, 1241, 1051, 905 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.92 (dd, J = 7.5, 0.9 Hz, 1 H), 7.53–7.47 (m, 1 H), 7.43–7.37 (m, 4 H), 7.07–7.02 (m, 2 H), 5.46 (dd, J = 12.9, 2.4 Hz, 1 H), 3.04 (dd, J = 17.1, 12.9 Hz, 1 H), 2.88 (dd, J = 16.8, 3.0 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 191.4, 161.2, 137.2, 136.2, 134.5, 128.9, 127.4, 127.0, 121.7, 120.8, 118.0, 78.7, 44.5.
HRMS (EI): m/z calcd for C15H11ClO2: 258.0448; found: 258.0446.
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2-(Naphthalen-2-yl)chroman-4-one (12f)
Yield: 195 mg (71%); colorless solid; mp 121–123 °C.
IR (KBr): 2893, 1607, 1574, 1462, 1396, 1342, 1300, 1221, 1028, 907 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.84 (d, J = 7.8 Hz, 1 H), 7.76–7.70 (m, 4 H), 7.43–7.33 (m, 4 H), 6.95–6.88 (m, 2 H), 5.47 (dd, J = 12.9, 3.0 Hz, 1 H), 3.01 (dd, J = 17.1, 13.2 Hz, 1 H), 2.84 (dd, J = 16.5, 2.7 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 191.5, 161.5, 136.1, 136.0, 133.3, 133.1, 128.6, 128.0, 127.6, 127.0, 126.4, 125.3, 123.6, 121.5, 121.0, 118.0, 115.0, 79.5, 44.5.
HRMS (EI): m/z calcd for C19H14O2: 274.0994; found: 274.0992.
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2-(5-Methylfuran-2-yl)chroman-4-one (12g)
Yield: 137 mg (60%); yellow solid; mp 124–126 °C.
IR (KBr): 2892, 1691, 1605, 1466, 1307, 1226, 1151, 1097, 886 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.84–7.81 (m, 1 H), 7.43–7.36 (m, 1 H), 6.97–6.92 (m, 2 H), 6.24 (d, J = 3.0 Hz, 1 H), 5.90–5.88 (m, 1 H), 5.39 (dd, J = 11.7, 3.3 Hz, 1 H), 3.19 (ddd, J = 16.8, 12.0, 0.6 Hz, 1 H), 2.87 (ddd, J = 17.1, 3.6, 0.9 Hz, 1 H), 2.23 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 191.5, 160.8, 153.4, 148.9, 136.1, 126.8, 121.5, 120.8, 118.1, 110.4, 106.4, 72.3, 40.7, 13.5.
HRMS (EI): m/z calcd for C14H12O3: 228.0786; found: 228.0787.
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6-Methyl-2-phenylchroman-4-one (12h)
Yield: 167 mg (70%); light yellow solid; mp 106–108 °C.
IR (KBr): 3033, 2916, 1695, 1612, 1489, 1417, 1370, 1289, 1226, 1057, 993, 911 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.55 (s, 1 H), 7.29–7.20 (m, 5 H), 7.11 (d, J = 7.8 Hz, 1 H), 6.76 (d, J = 8.4 Hz, 1 H), 5.21 (d, J = 12.3 Hz, 1 H), 2.84 (dd, J = 16.8, 13.2 Hz, 1 H), 2.64 (d, J = 16.8 Hz, 1 H), 2.14 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 191.7, 159.3, 138.7, 136.9, 130.7, 128.5, 128.4, 126.3, 125.9, 120.3, 117.6, 79.2, 44.3, 20.1.
HRMS (EI): m/z calcd for C16H14O2: 238.0994; found: 238.0993.
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2-(4-Methoxyphenyl)-6-methylchroman-4-one (12i)
Yield: 190 mg (71%); colorless solid; mp 108–110 °C.
IR (KBr): 2923, 1687, 1611, 1482, 1460, 1286, 1222, 1174, 1120, 1030, 906 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.58 (s, 1 H), 7.25 (d, J = 7.8 Hz, 2 H), 7.15 (d, J = 8.4 Hz, 1 H), 6.83–6.79 (m, 3 H), 5.21 (d, J = 12.9 Hz, 1 H), 3.69 (s, 3 H), 2.92 (dd, J = 16.2, 13.2 Hz, 1 H), 2.66 (d, J = 16.2 Hz, 1 H), 2.18 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 192.2, 159.7, 159.5, 137.0, 130.7, 130.7, 127.5, 126.3, 120.3, 117.7, 113.9, 79.0, 55.1, 44.2, 20.2.
HRMS (EI): m/z calcd for C17H16O3: 268.1099; found: 268.1096.
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2-(4-Bromophenyl)-6-methylchroman-4-one (12j)
Yield: 190 mg (60%); brown solid; mp 120–121 °C.
IR (KBr): 2913, 1692, 1612, 1488, 1415, 1291, 1225, 1164, 1064, 1005, 905 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.59 (s, 1 H), 7.42 (d, J = 8.1 Hz, 2 H), 7.25–7.19 (m, 3 H), 6.82 (d, J = 8.4 Hz, 1 H), 5.30 (dd, J = 12.9, 2.7 Hz, 1 H), 2.89 (dd, J = 16.8, 13.2 Hz, 1 H), 2.75 (dd, J = 16.5, 3.0 Hz, 1 H), 2.21 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 191.5, 159.2, 137.8, 137.2, 131.8, 131.1, 127.6, 126.5, 122.4, 120.3, 117.7, 78.6, 44.4, 20.3.
HRMS (EI): m/z calcd for C16H13BrO2: 316.0099; found: 316.0095.
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2-(2-Chlorophenyl)-6-methylchroman-4-one (12k)
Yield: 201 mg (74%); light yellow solid; mp 94–96 °C.
IR (KBr): 2920, 1691, 1618, 1489, 1422, 1364, 1290, 1226, 1133, 1061, 1003, 911, 823, 758 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.62 (s, 2 H), 7.28–7.15 (m, 4 H), 6.83 (d, J = 8.1 Hz, 1 H), 5.72 (dd, J = 13.2, 2.7 Hz, 1 H), 2.86 (dd, J = 16.8, 2.7 Hz, 1 H), 2.72 (dd, J = 17.1, 13.5 Hz, 1 H), 2.21 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 191.5, 159.4, 137.1, 136.7, 131.4, 131.1, 129.5, 129.4, 127.2, 127.1, 126.5, 120.4, 117.7, 76.3, 43.3, 20.3.
HRMS (EI): m/z calcd for C16H13ClO2: 272.0604; found: 272.0602.
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2-(4-Chlorophenyl)-6-methylchroman-4-one (12l)
Yield: 185 mg (68%); light yellow solid; mp 129–130 °C.
IR (KBr): 2903, 1692 1615, 1489, 1416, 1291, 1225, 1165, 1087, 1060, 993, 891 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.60 (s, 1 H), 7.29–7.21 (m, 4 H), 7.19 (d, J = 8.1 Hz, 1 H), 6.82 (d, J = 8.1 Hz, 1 H), 5.28 (dd, J = 12.6, 2.4 Hz, 1 H), 2.88 (dd, J = 16.5, 13.2 Hz, 1 H), 2.70 (dd, J = 16.5, 2.4 Hz, 1 H), 2.21 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 191.5, 159.2, 137.3, 137.2, 134.3, 131.1, 128.8, 127.3, 126.5, 120.3, 117.7, 78.6, 44.4, 20.3.
HRMS (EI): m/z calcd for C16H13ClO2: 272.0604; found: 272.0604.
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6-Methyl-1-(naphthalen-1-yl)chroman-4-one (12m)
Yield: 251 mg (87%); white solid; mp 138–140 °C.
IR (KBr): 3050, 2921, 1690, 1612, 1487, 1416, 1287, 1226, 1053, 978, 904 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.89–7.86 (m, 1 H), 7.75–7.69 (m, 2 H), 7.65–7.58 (m, 2 H), 7.39–7.34 (m, 3 H), 7.17 (dd, J = 8.4, 2.1 Hz, 1 H), 6.82 (d, J = 8.4 Hz, 1 H), 6.01 (dd, J = 13.2, 3.0 Hz, 1 H), 3.06 (dd, J = 17.1, 13.2 Hz, 1 H), 2.91 (dd, J = 17.1, 3.0 Hz, 1 H), 2.19 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 192.2, 159.6, 137.1, 134.1, 133.7, 131.0, 130.0, 129.1, 128.9, 126.5, 126.5, 125.8, 125.2, 123.6, 122.7, 120.5, 117.8, 76.5, 43.8, 20.3.
HRMS (EI): m/z calcd for C20H16O2: 288.1150; found: 288.1151.
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6-Methyl-2-(naphthalen-2-yl)chroman-4-one (12n)
Yield: 187 mg (65%); colorless solid; mp 129–131 °C.
IR (KBr): 3052, 2915, 1691, 1614, 1483, 1416, 1288, 1219, 1128, 1058, 1001, 907 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.81–7.75 (m, 4 H), 7.64 (s, 1 H), 7.46 (d, J = 8.7 Hz, 1 H), 7.42–7.39 (m, 2 H), 7.21 (d, J = 8.4 Hz, 1 H), 6.87 (d, J = 8.4 Hz, 1 H), 5.50 (dd, J = 12.9, 2.4 Hz, 1 H), 3.05 (dd, J = 16.8, 12.9 Hz, 1 H), 2.86 (dd, J = 16.8, 2.7 Hz, 1 H), 2.23 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 192.0, 159.5, 137.2, 136.1, 133.2, 133.1, 131.0, 128.6, 128.0, 127.6, 126.5, 126.4, 125.3, 123.6, 120.5, 117.5, 79.5, 44.6, 20.3.
HRMS (EI): m/z calcd for C20H16O2: 288.1150; found: 288.1153.
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6-Methyl-2-(5-methylfuran-2-yl)chroman-4-one (12o)
Yield: 126 mg (52%); yellow solid; mp 111–113 °C.
IR (KBr): 2916, 1636, 1560, 1489, 1364, 1295, 1183, 1016, 822 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.61 (d, J = 1.2 Hz, 1 H), 7.22–7.18 (m, 1 H), 6.81 (d, J = 8.1 Hz, 1 H), 6.23 (d, J = 3.0 Hz, 1 H), 5.89–5.88 (m, 1 H), 5.35 (dd, J = 11.7, 3.3 Hz, 1 H), 3.16 (ddd, J = 16.8, 11.7, 1.2 Hz, 1 H), 2.83 (ddd, J = 16.8, 3.3, 1.2 Hz, 1 H), 2.22 (s, 3 H), 2.21 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 191.7, 158.8, 153.3, 149.0, 137.1, 130.9, 126.4, 120.4, 117.8, 110.2, 106.4, 72.2, 40.7, 20.3, 13.5.
HRMS (EI): m/z calcd for C15H14O3: 242.0943; found: 242.0944.
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7-Methoxy-2-(3-methoxyphenyl)chroman-4-one (12p)
Yield: 205 mg (72%); white solid; mp 101–103 °C.
IR (KBr): 2994, 1697, 1609, 1444, 1251, 1159, 1055 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.74 (dd, J = 8.7, 2.4 Hz, 1 H), 7.20 (td, J = 8.1, 2.1 Hz, 1 H), 6.91 (s, 2 H), 6.79 (d, J = 8.1 Hz, 1 H), 6.48 (dt, J = 8.7, 2.1 Hz, 1 H), 6.36 (s, 1 H), 5.30 (dd, J = 13.2, 3.0 Hz, 1 H), 3.69 (s, 6 H), 2.87 (ddd, J = 16.5, 13.2, 2.7 Hz, 1 H), 2.70 (ddd, J = 16.5, 3.0, 2.7 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 190.1, 165.9, 163.2, 159.7, 140.2, 129.7, 128.5, 118.1, 114.6, 113.8, 111.7, 110.0, 100.7, 79.6, 55.4, 55.0, 44.1.
HRMS (EI): m/z calcd for C17H16O4: 284.1049; found: 284.1053.
#
2-(4-Bromophenyl)-7-methoxychroman-4-one (12q)
Yield: 203 mg (61%); colorless solid; mp 106–107 °C.
IR (KBr): 3063, 2954, 1678, 1604, 1439, 1256, 1118, 1058, 828 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.74 (d, J = 8.7 Hz, 1 H), 7.44 (d, J = 7.8 Hz, 2 H), 7.23 (d, J = 7.8 Hz, 2 H), 6.50 (d, J = 8.7 Hz, 1 H), 6.39 (s, 1 H), 5.30 (d, J = 12.5 Hz, 1 H), 3.73 (s, 3 H), 2.86 (dd, J = 16.5, 12.5 Hz, 1 H), 2.67 (d, J = 16.5 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 189.9, 166.1, 163.1, 137.7, 131.8, 128.6, 127.7, 122.5, 114.6, 110.2, 100.8, 79.0, 55.5, 44.0.
HRMS (EI): m/z calcd for C16H13BrO3: 332.0048; found: 332.0049.
#
2-(4-Chlorophenyl)-7-methoxychroman-4-one (12r)
Yield: 181 mg (63%); light yellow solid; mp 118–120 °C.
IR (KBr): 2963, 1695, 1605, 1594, 1258, 1019, 834 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.78 (d, J = 9.0 Hz, 1 H), 7.34–7.31 (m, 4 H), 6.55–6.51 (m, 1 H), 6.40 (s, 1 H), 5.37 (dd, J = 12.9, 2.7 Hz, 1 H), 3.75 (s, 3 H), 2.88 (dd, J = 16.8, 12.9 Hz, 1 H), 2.70 (dd, J = 16.2, 2.7 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 189.9, 166.2, 163.2, 137.3, 134.5, 128.9, 128.7, 127.4, 114.7, 110.3, 100.9, 79.1, 55.6, 44.1.
HRMS (EI): m/z calcd for C16H13ClO3: 288.0553; found: 288.0555.
#
7-Methoxy-2-(naphthalen-2-yl)chroman-4-one (12s)
Yield: 204 mg (67%); light yellow solid; mp 141–142 °C.
IR (KBr): 3048, 1674, 1604, 1438, 1328, 1198, 1117, 1022, 831 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.80–7.78 (m, 5 H), 7.47–7.41 (m, 3 H), 6.50 (d, J = 8.7 Hz, 1 H), 6.42 (s, 1 H), 5.47 (d, J = 12.6 Hz, 1 H), 3.71 (s, 3 H), 3.00 (dd, J = 16.5, 13.5 Hz, 1 H), 2.76 (d, J = 16.5 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 190.4, 166.1, 163.4, 136.0, 133.2, 133.0, 128.6, 128.0, 127.6, 126.4, 125.2, 123.5, 114.7, 110.2, 100.8, 79.9, 55.5, 44.2.
HRMS (EI): m/z calcd for C20H16O3: 304.1099; found: 304.1102.
#
7-Methoxyflavanone (1)
Yield: 158 mg (62%); light yellow solid; mp 88–90 °C.
IR (KBr): 2971, 1681, 1609, 1443, 1366, 1249, 1159, 1057, 841 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.87 (d, J = 8.7 Hz, 1 H), 7.47–7.34 (m, 5 H), 6.61 (dd, J = 8.7, 2.4 Hz, 1 H), 6.49 (d, J = 1.8 Hz, 1 H), 5.47 (dd, J = 12.9, 2.4 Hz, 1 H), 3.82 (s, 3 H), 3.02 (dd, J = 16.2, 13.2 Hz, 1 H), 2.84 (dd, J = 16.8, 3.0 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 190.0, 165.8, 163.2, 138.6, 128.5, 128.5, 128.4, 125.9, 114.6, 109.9, 100.7, 79.6, 55.3, 44.0.
HRMS (EI): m/z calcd for C16H14O3: 254.0943; found: 254.0942.
#
4′,7-Dimethoxyflavanone (2)
Yield: 168 mg (59%); light yellow solid; mp 80–81 °C.
IR (KBr): 2961, 1690, 1610, 1444, 1255, 1159, 1029, 833 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.70 (dd, J = 9.0, 2.7 Hz, 1 H), 7.24–7.21 (m, 2 H), 6.80–6.77 (m, 2 H), 6.45–6.40 (m, 1 H), 6.30 (s, 1 H), 5.22 (d, J = 13.2 Hz, 1 H), 3.65 (t, J = 2.7 Hz, 6 H), 2.85 (ddd, J = 16.5, 13.2, 3.0 Hz, 1 H), 2.57 (dd, J = 16.5, 3.0 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 190.2, 165.7, 163.2, 159.6, 130.6, 128.3, 127.4, 114.5, 113.8, 109.7, 100.6, 79.3, 55.2, 54.9, 43.7.
HRMS (EI): m/z calcd for C17H16O4: 284.1049; found: 284.1048.
#
5,7-Dimethoxyflavanone (3)
Yield: 156 mg (55%); light yellow solid; mp 142–144 °C.
IR (KBr): 3062, 2941, 1676, 1609, 1570, 1423, 1217, 1159, 1111, 1067, 823 cm–1.
1H NMR (300 MHz, CDCl3): δ = 7.34–7.23 (m, 5 H), 6.03 (s, 1 H), 5.97 (s, 1 H), 5.29 (dd, J = 12.9, 2.4 Hz, 1 H), 3.76 (s, 3 H), 3.68 (s, 3 H), 2.89 (dd, J = 16.5, 14.1 Hz, 1 H), 2.69 (dd, J = 16.5, 2.7 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 188.7, 165.7, 164.7, 162.0, 138.6, 128.5, 128.3, 125.8, 105.7, 93.3, 92.9, 78.9, 55.8, 55.3, 45.3.
HRMS (EI): m/z calcd for C17H16O4: 284.1049; found: 284.1046.
#
#
Acknowledgment
This research was supported by the Nano Material Technology Development Program of the Korean National Research Foundation (NRF) funded by the Korean Ministry of Education, Science, and Technology (2012M3A7B4049675).
Supporting Information
- for this article is available online at http://www.thieme-connect.com.accesdistant.sorbonne-universite.fr/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Shakil NA, Kumar PJ, Pandey RK, Saxena DB. Phytochemistry 2008; 69: 759
- 1b Al-Rehaily AJ, Albishi OA, El-Olemy MM, Mossa JS. Phytochemistry 2008; 69: 1910
- 1c Umehara K, Nemoto K, Matsushita A, Terada E, Monthakantirat O, De-Eknamkul W, Miyase T, Warashina T, Degawa M, Noguchi H. J. Nat. Prod. 2009; 72: 2163
- 1d Radwan MM, Rodriguez-Guzman R, Manly SP, Jacob M, Ross SA. Phytochem. Lett. 2009; 2: 141
- 1e Win T, Htwe TT, Shwe HH, Heilmann J. Chemistry & Biodiversity 2012; 9: 1198
- 2a Wang Y, Tan W, Li WZ, Li Y. J. Nat. Prod. 2001; 64: 196
- 2b Harborne JB, Williams CA. Nat. Prod. Rep. 2001; 18: 310
- 2c Middleton E, Kandaswami C. Food Technol. 1994; 48: 115
- 2d Nijveldt RJ, Nood E, Hoorn DE. C, Boelens PG, Norren K, Leeuwen PA. M. Am. J. Clin. Nutr. 2001; 74: 418
- 3a Chiari ME, Vera DM. A, Palacios SM, Carpinella MC. Bioorg. Med. Chem. 2011; 19: 3474
- 3b Saewan N, Koysomboon S, Chantrapromma K. J. Med. Plant Res. 2011; 5: 1018
- 3c Peralta MA, Ortega MG, Agnese AM, Cabrera JL. J. Nat. Prod. 2011; 74: 158
- 3d Itoh K, Hirata N, Masuda M, Naruto S, Murata K, Wakabayashi K, Matsuda H. Biol. Pharm. Bull. 2009; 32: 410
- 4a Yoo NH, Jang DS, Yoo JL, Lee YM, Kim YS, Cho J.-H, Kim JS. J. Nat. Prod. 2008; 71: 713
- 4b Matsuda H, Morikawa T, Toguchida I, Harima S, Yoshikawa M. Chem. Pharm. Bull. 2002; 50: 972
- 4c Matsuda H, Morikawa T, Toguchida I, Yoshikawa M. Chem. Pharm. Bull. 2002; 50: 788
- 4d Matsuda H, Nishida N, Yoshikawa M. Chem. Pharm. Bull. 2002; 50: 429
- 4e Lim SS, Jung SH, Ji J, Shin KH, Keum SR. J. Pharm. Pharmacol. 2001; 53: 653
- 5a Muftuoglu Y, Mustata G. Bioorg. Med. Chem. Lett. 2010; 20: 3050
- 5b Paoletta S, Steventon GB, Wildeboer D, Ehrman TM, Hylands PJ, Barlow DJ. Bioorg. Med. Chem. 2008; 16: 8466
- 5c Yahiaoui S, Fagnere C, Pouget C, Buxeraud J, Chulia A.-J. Bioorg. Med. Chem. 2008; 16: 1474
- 5d Maiti A, Cuendet M, Croy VL, Endringer DC, Pezzuto JM, Cushman M. J. Med. Chem. 2007; 50: 2799
- 5e Nagar S, Islam MA, Das S, Mukherjee A, Saha A. Mol. Diversity 2008; 12: 65
- 5f Moriarty RM, Grubjesic S, Surve BC, Chandersekera SN, Prakash O, Naithani R. Eur. J. Med. Chem. 2006; 41: 263
- 6a Haslam E. Shikimic Acid Metabolism and Metabolites . Wiley; Chichester: 1993: 331
- 6b Mann J. Chemical Aspects of Biosynthesis . Oxford University Press; Oxford: 1994: 58
- 6c Li W.-DZ, Ma B.-C. Org. Lett. 2005; 7: 271
- 6d Urgaonkar S, Pierre HS. L, Meir I, Lund H, RayChaudhuri D, Shaw JT. Org. Lett. 2005; 7: 5609
- 7 Ma X-M, Liu Y, Shi Y.-P. Chemistry & Biodiversity 2007; 4: 2172
- 8 Garcez FR, Garcez WS, Santana AL. B. D, Matos Alves MM, Matos MD. F. C, Scaliante AD. M. J. Braz. Chem. Soc. 2006; 17: 1223
- 9a Pouget C, Lauthier F, Simon A, Fagnere C, Basly J.-P, Delage C, Chulia A.-J. Bioorg. Med. Chem. 2001; 11: 3095
- 9b Sivakumar PM, Babu SK. G, Mukesh D. Chem. Pharm. Bull. 2007; 55: 44
- 9c Putz MV, Putz A.-M, Lazea M, Ienciu L, Chiriac A. Int. J. Mol. Sci. 2009; 10: 1193
- 9d Nishizaki Y, Ishimoto Y, Hotta Y, Hosoda A, Yoshikawa H, Akamatsu M, Tamura H. Bioorg. Med. Chem. Lett. 2009; 19: 4706
- 9e Choi EJ, Lee JI, Kim G.-H. Arch. Pharm. Res. 2011; 34: 2125
- 10 Wu D, Nair MG, DeWitt DL. J. Agric. Food Chem. 2002; 50: 701
- 11 Katerere DR, Gray AI, Nash RJ, Waigh RD. Fitoterapia 2012; 83: 932
- 12 Thuy TT. T, Quan TD, Anh NT. H, Sung TV. Nat. Prod. Res. 2011; 25: 1361
- 13 Rajudin E, Ahmad F, Sirat HM, Arbain D, Aboul-Enein HY. Nat. Prod. Res. 2010; 24: 387
- 14 Wang L, Wu M, Tang Z, Yang X, Lei Y, Wang L, Yin B, Chen Y. Biochem. Syst. Ecol. 2012; 43: 48
- 15 Wang F, Zhou D.-S, Wei G.-Z, Ren F.-C, Liu J.-K. Phytochemistry 2012; 77: 312
- 16a Dzoyem JP, Kuete AH. L, Kuete V, Tala MF, Wabo HK, Guru SK, Rajput VS, Sharma A, Tane P, Khan IA, Saxena AK, Laatsch H, Tan N.-H. Planta Med. 2012; 78: 787
- 16b Orhan DD, Oezcelik B, Oezgen S, Ergun F. Microbiol. Res. 2010; 165: 496
- 16c Rao YK, Geethangili M, Fang S.-H, Tzeng Y.-M. Food Chem. Toxicol. 2007; 45: 1770
- 16d Ying H, Hu Y, He Q, Li R, Yang B. Eur. J. Med. Chem. 2007; 42: 226
- 16e Rao YK, Fang S.-H, Tzeng Y.-M. J. Ethnopharmacol. 2005; 100: 249
- 17 Peng L, Yang S, Cheng YJ, Chen F, Pan S, Fan G. Food Sci. Biotechnol. 2012; 21: 1533
- 18 Aderogba MA, Kgatle DT, McGaw LJ, Eloff JN. S. Afr. J. Bot. 2012; 79: 125
- 19 Wangkangwan W, Boonkerd S, Chavasiri W, Sukapirom K, Pattanapanyasat K, Kongkathip N, Miyakawa T, Yompakdee C. Biosci. Biotechnol. Biochem. 2009; 73: 1679
- 20a Yang H, Dong Y, Du H, Shi H, Peng Y, Li X. Molecules 2011; 16: 3444
- 20b Li F, Awale S, Tezuka Y, Kadota S. Nat. Prod. Commun. 2010; 5: 1601
- 20c Jantan I, Pisar M, Sirat HM, Basar N, Jamil S, Ali RM, Jalil J. Phytother. Res. 2004; 18: 1005
- 20d Grael CF. F, Albuquerque S, Lopes JL. C. Fitoterapia 2005; 76: 73
- 21 Seligmann O, Wagner H. Tetrahedron 1981; 37: 2601
- 22a Pick A, Mueller H, Mayer R, Haenisch B, Pajeva IK, Weigt M, Boenisch H, Mueller CE, Wiese M. Bioorg. Med. Chem. 2011; 19: 2090
- 22b Boonphong S, Puangsombat P, Baramee A, Mahidol C, Ruchirawat S, Kittakoop P. J. Nat. Prod. 2007; 70: 795
- 22c Portet B, Fabre N, Roumy V, Gornitzka H, Bourdy G, Chevalley S, Sauvain M, Valentin A, Moulis C. Phytochemistry 2007; 68: 1312
- 22d Rubio S, Quintana J, Lopez M, Eiroa JL, Triana J, Estevez F. Eur. J. Pharmacol. 2006; 548: 9
- 22e Gafner S, Wolfender J.-L, Mavi S, Hostettmann K. Planta Med. 1996; 62: 67
- 23 Dao T.-T, Tung B.-T, Nguyen P.-H, Thuong P.-T, Yoo S.-S, Kim E.-H, Kim S.-K, Oh W.-K. J. Nat. Prod. 2010; 73: 1636
- 24 Kaulich M, Streicher F, Mayer R, Müller I, Müller CE. Drug Develop. Res. 2003; 59: 72
- 25 Kuo Y.-C, Yang L.-M, Lin L.-C. Planta Med. 2004; 70: 1237
- 26a Cheng PL, Fournari P, Tirouflet J. Bull. Soc. Chim. Fr. 1963; 2248
- 26b Reichel L, Proksch G. Liebigs Ann. Chem. 1971; 745: 59
- 26c Nabaei-Bidhendi G, Bannerjee NR. J. Indian Chem. Soc. 1990; 67: 43
- 26d Brennan CM, Hunt I, Jarvis TC, Johnson CD, McDonnell PD. Can. J. Chem. 1990; 68: 1780
- 26e Wurm G, Schnetzer D. Arch. Pharm. (Weinheim) 1992; 325: 717
- 26f Chaturvedi R, Patil PN, Mulchandani NB. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1992; 31: 340
- 27a Keane DD, Marathe KG, O’Sullivan WI, Philbin EM, Simons RM, Teague PC. J. Org. Chem. 1970; 35: 2286
- 27b Reichel L, Weber FG. Pharmazie 1975; 30: 195
- 27c Dutta CP, Roy LP. K. Indian J. Chem. 1975; 13: 425
- 27d Patonay T, Litkei G, Zsuga M, Kiss A. Org. Prep. Proced. Int. 1984; 16: 315
- 27e Thomsen I, Torssell BG. Acta Chem. Scand., Ser. B 1988; 42: 303
- 27f Climent MJ, Garcia H, Iborra S, Miranda MA, Primo J. Heterocycles 1989; 29: 115
- 27g Bagade MB, Thool AW, Lokhande PD, Ghiya BJ. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. 1991; 30: 973
- 28a Stermitz FR, Adamovics JA, Geigert J. Tetrahedron 1975; 31: 1593
- 28b Matsushima R, Kageyama H. J. Chem. Soc., Perkin Trans. 2 1985; 743
- 28c Pandey G, Krishna A, Kumaraswamy G. Tetrahedron Lett. 1987; 28: 4615
- 28d Maki Y, Shimada K, Sako M, Hirota K. Tetrahedron 1988; 44: 3187
- 29 Sanicanin Z, Tabakovic I. Tetrahedron Lett. 1986; 27: 407
- 30a Bhatia VK, Krishnamurty HG, Madhav R, Seshadri TR. Tetrahedron Lett. 1968; 3859
- 30b Jyotsna D, Rao AV. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1987; 26: 877
- 30c Izumi T, Hino T, Kasahara A. J. Chem. Soc., Perkin Trans. 1 1992; 1265
- 30d Sing OV. Org. Prep. Proced. Int. 1993; 25: 693
- 31 Subramanian RS, Balasubramanian KK. J. Chem. Soc., Chem. Commun. 1990; 1469
- 32 Wang L, Liu X, Dong Z, Fu X, Feng X. Angew. Chem. Int. Ed. 2008; 47: 8670
- 33 Kumar A, Sharma S, Tripathi VD, Srivastava S. Tetrahedron 2010; 66: 9445
- 34 Dubrovskiy AV, Larock RC. Org. Lett. 2010; 12: 3117
- 35 Chen P.-Y, Wang T.-P, Chiang MY, Huang K.-S, Tzeng C.-C, Chen Y.-L, Wang E.-C. Tetrahedron 2011; 67: 4155
- 36 Kavala V, Lin C, Kuo C.-W, Fang H, Yao C.-F. Tetrahedron 2012; 68: 1321
- 37a Hudlicky T. Chem. Rev. 1996; 96: 3
- 37b Arend M, Westermann B, Risch N. Angew. Chem. Int. Ed. 1998; 37: 1044
- 37c Kobayashi S, Ishitani H. Chem. Rev. 1999; 99: 1069
- 38a Berrisford DJ, Bolm C, Sharpless KB. Angew. Chem. Int., Ed. Engl. 1995; 34: 1059
- 38b Saito S, Nakadai M, Yamamoto H. Synlett 2001; 1245
- 38c Saito S, Yamamoto H. Acc. Chem. Res. 2004; 37: 570
- 38d Bolm C, Rantanen T, Schiffers I, Zani L. Angew. Chem. Int. Ed. 2005; 44: 1758
- 39a Lee YR, Choi JH, Yoon SH. Tetrahedron Lett. 2005; 46: 7539
- 39b Lee YR, Kim DH. Synthesis 2006; 603
- 39c Lee YR, Kim JH. Synlett 2007; 2232
- 39d Lee YR, Xia L. Synthesis 2007; 3240
- 39e Lee YR, Kim YM. Helv. Chim. Acta 2007; 90: 2401
- 39f Lee YR, Li X, Kim JH. J. Org. Chem. 2008; 73: 4313
- 39g Xia L, Lee YR. Synlett 2008; 1643
- 39h Lee YR, Xia L. Tetrahedron Lett. 2008; 49: 3283
- 39i Wang X, Lee YR. Tetrahedron 2009; 65: 10125
- 39j Wang X, Lee YR. Tetrahedron 2011; 67: 9179
- 39k Pandit RP, Lee YR. Synthesis 2012; 44: 2910
-
References
- 1a Shakil NA, Kumar PJ, Pandey RK, Saxena DB. Phytochemistry 2008; 69: 759
- 1b Al-Rehaily AJ, Albishi OA, El-Olemy MM, Mossa JS. Phytochemistry 2008; 69: 1910
- 1c Umehara K, Nemoto K, Matsushita A, Terada E, Monthakantirat O, De-Eknamkul W, Miyase T, Warashina T, Degawa M, Noguchi H. J. Nat. Prod. 2009; 72: 2163
- 1d Radwan MM, Rodriguez-Guzman R, Manly SP, Jacob M, Ross SA. Phytochem. Lett. 2009; 2: 141
- 1e Win T, Htwe TT, Shwe HH, Heilmann J. Chemistry & Biodiversity 2012; 9: 1198
- 2a Wang Y, Tan W, Li WZ, Li Y. J. Nat. Prod. 2001; 64: 196
- 2b Harborne JB, Williams CA. Nat. Prod. Rep. 2001; 18: 310
- 2c Middleton E, Kandaswami C. Food Technol. 1994; 48: 115
- 2d Nijveldt RJ, Nood E, Hoorn DE. C, Boelens PG, Norren K, Leeuwen PA. M. Am. J. Clin. Nutr. 2001; 74: 418
- 3a Chiari ME, Vera DM. A, Palacios SM, Carpinella MC. Bioorg. Med. Chem. 2011; 19: 3474
- 3b Saewan N, Koysomboon S, Chantrapromma K. J. Med. Plant Res. 2011; 5: 1018
- 3c Peralta MA, Ortega MG, Agnese AM, Cabrera JL. J. Nat. Prod. 2011; 74: 158
- 3d Itoh K, Hirata N, Masuda M, Naruto S, Murata K, Wakabayashi K, Matsuda H. Biol. Pharm. Bull. 2009; 32: 410
- 4a Yoo NH, Jang DS, Yoo JL, Lee YM, Kim YS, Cho J.-H, Kim JS. J. Nat. Prod. 2008; 71: 713
- 4b Matsuda H, Morikawa T, Toguchida I, Harima S, Yoshikawa M. Chem. Pharm. Bull. 2002; 50: 972
- 4c Matsuda H, Morikawa T, Toguchida I, Yoshikawa M. Chem. Pharm. Bull. 2002; 50: 788
- 4d Matsuda H, Nishida N, Yoshikawa M. Chem. Pharm. Bull. 2002; 50: 429
- 4e Lim SS, Jung SH, Ji J, Shin KH, Keum SR. J. Pharm. Pharmacol. 2001; 53: 653
- 5a Muftuoglu Y, Mustata G. Bioorg. Med. Chem. Lett. 2010; 20: 3050
- 5b Paoletta S, Steventon GB, Wildeboer D, Ehrman TM, Hylands PJ, Barlow DJ. Bioorg. Med. Chem. 2008; 16: 8466
- 5c Yahiaoui S, Fagnere C, Pouget C, Buxeraud J, Chulia A.-J. Bioorg. Med. Chem. 2008; 16: 1474
- 5d Maiti A, Cuendet M, Croy VL, Endringer DC, Pezzuto JM, Cushman M. J. Med. Chem. 2007; 50: 2799
- 5e Nagar S, Islam MA, Das S, Mukherjee A, Saha A. Mol. Diversity 2008; 12: 65
- 5f Moriarty RM, Grubjesic S, Surve BC, Chandersekera SN, Prakash O, Naithani R. Eur. J. Med. Chem. 2006; 41: 263
- 6a Haslam E. Shikimic Acid Metabolism and Metabolites . Wiley; Chichester: 1993: 331
- 6b Mann J. Chemical Aspects of Biosynthesis . Oxford University Press; Oxford: 1994: 58
- 6c Li W.-DZ, Ma B.-C. Org. Lett. 2005; 7: 271
- 6d Urgaonkar S, Pierre HS. L, Meir I, Lund H, RayChaudhuri D, Shaw JT. Org. Lett. 2005; 7: 5609
- 7 Ma X-M, Liu Y, Shi Y.-P. Chemistry & Biodiversity 2007; 4: 2172
- 8 Garcez FR, Garcez WS, Santana AL. B. D, Matos Alves MM, Matos MD. F. C, Scaliante AD. M. J. Braz. Chem. Soc. 2006; 17: 1223
- 9a Pouget C, Lauthier F, Simon A, Fagnere C, Basly J.-P, Delage C, Chulia A.-J. Bioorg. Med. Chem. 2001; 11: 3095
- 9b Sivakumar PM, Babu SK. G, Mukesh D. Chem. Pharm. Bull. 2007; 55: 44
- 9c Putz MV, Putz A.-M, Lazea M, Ienciu L, Chiriac A. Int. J. Mol. Sci. 2009; 10: 1193
- 9d Nishizaki Y, Ishimoto Y, Hotta Y, Hosoda A, Yoshikawa H, Akamatsu M, Tamura H. Bioorg. Med. Chem. Lett. 2009; 19: 4706
- 9e Choi EJ, Lee JI, Kim G.-H. Arch. Pharm. Res. 2011; 34: 2125
- 10 Wu D, Nair MG, DeWitt DL. J. Agric. Food Chem. 2002; 50: 701
- 11 Katerere DR, Gray AI, Nash RJ, Waigh RD. Fitoterapia 2012; 83: 932
- 12 Thuy TT. T, Quan TD, Anh NT. H, Sung TV. Nat. Prod. Res. 2011; 25: 1361
- 13 Rajudin E, Ahmad F, Sirat HM, Arbain D, Aboul-Enein HY. Nat. Prod. Res. 2010; 24: 387
- 14 Wang L, Wu M, Tang Z, Yang X, Lei Y, Wang L, Yin B, Chen Y. Biochem. Syst. Ecol. 2012; 43: 48
- 15 Wang F, Zhou D.-S, Wei G.-Z, Ren F.-C, Liu J.-K. Phytochemistry 2012; 77: 312
- 16a Dzoyem JP, Kuete AH. L, Kuete V, Tala MF, Wabo HK, Guru SK, Rajput VS, Sharma A, Tane P, Khan IA, Saxena AK, Laatsch H, Tan N.-H. Planta Med. 2012; 78: 787
- 16b Orhan DD, Oezcelik B, Oezgen S, Ergun F. Microbiol. Res. 2010; 165: 496
- 16c Rao YK, Geethangili M, Fang S.-H, Tzeng Y.-M. Food Chem. Toxicol. 2007; 45: 1770
- 16d Ying H, Hu Y, He Q, Li R, Yang B. Eur. J. Med. Chem. 2007; 42: 226
- 16e Rao YK, Fang S.-H, Tzeng Y.-M. J. Ethnopharmacol. 2005; 100: 249
- 17 Peng L, Yang S, Cheng YJ, Chen F, Pan S, Fan G. Food Sci. Biotechnol. 2012; 21: 1533
- 18 Aderogba MA, Kgatle DT, McGaw LJ, Eloff JN. S. Afr. J. Bot. 2012; 79: 125
- 19 Wangkangwan W, Boonkerd S, Chavasiri W, Sukapirom K, Pattanapanyasat K, Kongkathip N, Miyakawa T, Yompakdee C. Biosci. Biotechnol. Biochem. 2009; 73: 1679
- 20a Yang H, Dong Y, Du H, Shi H, Peng Y, Li X. Molecules 2011; 16: 3444
- 20b Li F, Awale S, Tezuka Y, Kadota S. Nat. Prod. Commun. 2010; 5: 1601
- 20c Jantan I, Pisar M, Sirat HM, Basar N, Jamil S, Ali RM, Jalil J. Phytother. Res. 2004; 18: 1005
- 20d Grael CF. F, Albuquerque S, Lopes JL. C. Fitoterapia 2005; 76: 73
- 21 Seligmann O, Wagner H. Tetrahedron 1981; 37: 2601
- 22a Pick A, Mueller H, Mayer R, Haenisch B, Pajeva IK, Weigt M, Boenisch H, Mueller CE, Wiese M. Bioorg. Med. Chem. 2011; 19: 2090
- 22b Boonphong S, Puangsombat P, Baramee A, Mahidol C, Ruchirawat S, Kittakoop P. J. Nat. Prod. 2007; 70: 795
- 22c Portet B, Fabre N, Roumy V, Gornitzka H, Bourdy G, Chevalley S, Sauvain M, Valentin A, Moulis C. Phytochemistry 2007; 68: 1312
- 22d Rubio S, Quintana J, Lopez M, Eiroa JL, Triana J, Estevez F. Eur. J. Pharmacol. 2006; 548: 9
- 22e Gafner S, Wolfender J.-L, Mavi S, Hostettmann K. Planta Med. 1996; 62: 67
- 23 Dao T.-T, Tung B.-T, Nguyen P.-H, Thuong P.-T, Yoo S.-S, Kim E.-H, Kim S.-K, Oh W.-K. J. Nat. Prod. 2010; 73: 1636
- 24 Kaulich M, Streicher F, Mayer R, Müller I, Müller CE. Drug Develop. Res. 2003; 59: 72
- 25 Kuo Y.-C, Yang L.-M, Lin L.-C. Planta Med. 2004; 70: 1237
- 26a Cheng PL, Fournari P, Tirouflet J. Bull. Soc. Chim. Fr. 1963; 2248
- 26b Reichel L, Proksch G. Liebigs Ann. Chem. 1971; 745: 59
- 26c Nabaei-Bidhendi G, Bannerjee NR. J. Indian Chem. Soc. 1990; 67: 43
- 26d Brennan CM, Hunt I, Jarvis TC, Johnson CD, McDonnell PD. Can. J. Chem. 1990; 68: 1780
- 26e Wurm G, Schnetzer D. Arch. Pharm. (Weinheim) 1992; 325: 717
- 26f Chaturvedi R, Patil PN, Mulchandani NB. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1992; 31: 340
- 27a Keane DD, Marathe KG, O’Sullivan WI, Philbin EM, Simons RM, Teague PC. J. Org. Chem. 1970; 35: 2286
- 27b Reichel L, Weber FG. Pharmazie 1975; 30: 195
- 27c Dutta CP, Roy LP. K. Indian J. Chem. 1975; 13: 425
- 27d Patonay T, Litkei G, Zsuga M, Kiss A. Org. Prep. Proced. Int. 1984; 16: 315
- 27e Thomsen I, Torssell BG. Acta Chem. Scand., Ser. B 1988; 42: 303
- 27f Climent MJ, Garcia H, Iborra S, Miranda MA, Primo J. Heterocycles 1989; 29: 115
- 27g Bagade MB, Thool AW, Lokhande PD, Ghiya BJ. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. 1991; 30: 973
- 28a Stermitz FR, Adamovics JA, Geigert J. Tetrahedron 1975; 31: 1593
- 28b Matsushima R, Kageyama H. J. Chem. Soc., Perkin Trans. 2 1985; 743
- 28c Pandey G, Krishna A, Kumaraswamy G. Tetrahedron Lett. 1987; 28: 4615
- 28d Maki Y, Shimada K, Sako M, Hirota K. Tetrahedron 1988; 44: 3187
- 29 Sanicanin Z, Tabakovic I. Tetrahedron Lett. 1986; 27: 407
- 30a Bhatia VK, Krishnamurty HG, Madhav R, Seshadri TR. Tetrahedron Lett. 1968; 3859
- 30b Jyotsna D, Rao AV. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1987; 26: 877
- 30c Izumi T, Hino T, Kasahara A. J. Chem. Soc., Perkin Trans. 1 1992; 1265
- 30d Sing OV. Org. Prep. Proced. Int. 1993; 25: 693
- 31 Subramanian RS, Balasubramanian KK. J. Chem. Soc., Chem. Commun. 1990; 1469
- 32 Wang L, Liu X, Dong Z, Fu X, Feng X. Angew. Chem. Int. Ed. 2008; 47: 8670
- 33 Kumar A, Sharma S, Tripathi VD, Srivastava S. Tetrahedron 2010; 66: 9445
- 34 Dubrovskiy AV, Larock RC. Org. Lett. 2010; 12: 3117
- 35 Chen P.-Y, Wang T.-P, Chiang MY, Huang K.-S, Tzeng C.-C, Chen Y.-L, Wang E.-C. Tetrahedron 2011; 67: 4155
- 36 Kavala V, Lin C, Kuo C.-W, Fang H, Yao C.-F. Tetrahedron 2012; 68: 1321
- 37a Hudlicky T. Chem. Rev. 1996; 96: 3
- 37b Arend M, Westermann B, Risch N. Angew. Chem. Int. Ed. 1998; 37: 1044
- 37c Kobayashi S, Ishitani H. Chem. Rev. 1999; 99: 1069
- 38a Berrisford DJ, Bolm C, Sharpless KB. Angew. Chem. Int., Ed. Engl. 1995; 34: 1059
- 38b Saito S, Nakadai M, Yamamoto H. Synlett 2001; 1245
- 38c Saito S, Yamamoto H. Acc. Chem. Res. 2004; 37: 570
- 38d Bolm C, Rantanen T, Schiffers I, Zani L. Angew. Chem. Int. Ed. 2005; 44: 1758
- 39a Lee YR, Choi JH, Yoon SH. Tetrahedron Lett. 2005; 46: 7539
- 39b Lee YR, Kim DH. Synthesis 2006; 603
- 39c Lee YR, Kim JH. Synlett 2007; 2232
- 39d Lee YR, Xia L. Synthesis 2007; 3240
- 39e Lee YR, Kim YM. Helv. Chim. Acta 2007; 90: 2401
- 39f Lee YR, Li X, Kim JH. J. Org. Chem. 2008; 73: 4313
- 39g Xia L, Lee YR. Synlett 2008; 1643
- 39h Lee YR, Xia L. Tetrahedron Lett. 2008; 49: 3283
- 39i Wang X, Lee YR. Tetrahedron 2009; 65: 10125
- 39j Wang X, Lee YR. Tetrahedron 2011; 67: 9179
- 39k Pandit RP, Lee YR. Synthesis 2012; 44: 2910
