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A new and efficient method for the synthesis of 3-(2-nitrophenyl)pyruvic acid derivatives and indoles based on the Reissert reaction |
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| Authors: | Vakhid A Mamedov Vera L Mamedova Victor V Syakaev Gul&#x;naz Z Khikmatova Dmitry E Korshin Temur A Kushatov Shamil K Latypov |
| Institution: | A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, Russian Federation |
| Abstract: | The formation of 3-(2-nitrophenyl)pyruvic acid and its amide and ester derivatives – key compounds for the Reissert indole synthesis – was achieved under various reaction conditions via the acid catalyzed hydrolysis of 5-(2-nitrobenzyliden)-2,2-dimethyl-1,3-oxazolidin-4-one, which is readily available from 3-(2-nitrophenyl)oxirane-2-carboxamide. A new and highly efficient method for the synthesis of indole-2-carboxylic acid derivatives via the intramolecular reductive cyclization of o-nitrophenylpyruvic acid and its amide and ester derivatives was developed using Na2S2O4 in dioxane/water at reflux. |
| Keywords: | 3-(2-Nitrophenyl)oxirane-2-carboxamide 5-(2-Nitrobenzyliden)-2 2-dimethyl-1 3-oxazolidin-4-one 3-(2-Nitrophenyl)pyruvic acid derivatives Intramolecular reductive cyclization Indole-2-carboxylic acid derivatives |
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