2020
DOI: 10.1021/acs.joc.0c01484
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Environmentally Friendly Protocol for 2,3-Difunctionlization of Indole Derivatives

Abstract: Environmentally friendly and highly regioselective C-3 dichlorination and C-2 oxidation of N-substituted indoles have been established using NaCl as a chlorine source and H2O as an oxygen source. A series of 3,3-dichloro-2-oxindoles were obtained in moderate to excellent yields. The gram-scale synthesis and derivatization reaction were explored. The possible mechanism for this reaction was elucidated.

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Cited by 8 publications
(9 citation statements)
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“…The residue was purified by flash chromatography (silica gel, eluent: petroleum ether/ethyl acetate = 4:1) to afford the product 2b (23. 3 2,3-Dimethoxy-5-methyl-1-(pyrimidin-2-yl)indoline (2c). The general procedure described above was followed using substrate 1c (20.9 mg, 0.1 mmol), PhIO (66.0 mg, 0.3 mmol), C 5 H 5 N•9HF (0.045 mL, 0.5 mmol), and MeOH (2.0 mL).…”
Section: 3-dimethoxy-4-methyl-1-(pyrimidin-2-yl)indoline (2b)mentioning
confidence: 99%
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“…The residue was purified by flash chromatography (silica gel, eluent: petroleum ether/ethyl acetate = 4:1) to afford the product 2b (23. 3 2,3-Dimethoxy-5-methyl-1-(pyrimidin-2-yl)indoline (2c). The general procedure described above was followed using substrate 1c (20.9 mg, 0.1 mmol), PhIO (66.0 mg, 0.3 mmol), C 5 H 5 N•9HF (0.045 mL, 0.5 mmol), and MeOH (2.0 mL).…”
Section: 3-dimethoxy-4-methyl-1-(pyrimidin-2-yl)indoline (2b)mentioning
confidence: 99%
“…White solid; 1 H NMR (500 MHz, CDCl 3 ) δ 7.62 (d, J = 8.2 Hz, 1H), 7.60−7.56 (m, 2H), 7.35−7.31 (m, 1H), 7.28 (d, J = 7.5 Hz, 1H), 7.14 (d, J = 8.1 Hz, 2H), 7.08 (td, J = 7.5 and 0.9 Hz, 1H), 5.33 (s, 1H), 4.25 (s, 1H), 3.59 (s, 3H), 3.18 (s, 3H), 2.31 (s, 3H). 13 2-Bromo-3-methoxy-1-(pyrimidin-2-yl)-1H-indole (3). In a 10 mL round-bottom flask were placed substrate 2a (25.7 mg, 0.1 mmol), NBS (19.6 mg, 0.11 mmol), and DCM (1.5 mL).…”
Section: -(5-fluoropyrimidin-2-yl)-23-dimethoxyindoline (2s)mentioning
confidence: 99%
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“…On the basis of these pioneering and excellent studies, as well as our ongoing efforts to develop green and sustainable methods for oxindole synthesis, 20 we report our recent progress in preparing oxindole through activation with keto acid and organic photosensitive compounds under irradiation with visible light. First, the substrate N -methyl- N -phenylmethacrylamide ( 5a ) was selected as a model starting material to investigate the reaction.…”
mentioning
confidence: 99%