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SYNTHESIS OF 4-ETHOXYCARBONYL(CYANO)-β-CARBOLINES via THERMOLYSIS OF 4-ARYL-3(5)-AZIDOPYRIDINE DERIVATIVES AND THE STUDY OF THEIR OPTICAL AND HYPOGLYCEMIC PROPERTIES

Виктория A. Прощенкова, Владислав Ю. Шувалов, Лариса В. Глиздинская, Александр С. Фисюк, Сергей А. Черненко, Михаил В. Хвостов, Татьяна Г. Толстикова, Марина А. Воронцова, Галина П. Сагитуллина
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Abstract


4-Ethoxycarbonyl(cyano)-1,3-dimethyl-β-carbolines were synthesized via thermolysis of 4-aryl-3(5)-azidopyridines and their optical and hypoglycemic properties were studied. For the first time, the accessible Hantzsch nitropyridines were used as the starting materials. Diazotization of 3-aminopyridines having a trimethoxyaryl substituent at the C-4 position of the pyridine ring by intramolecular azo coupling afforded 7,8,9-trimethoxy-2,4-dimethylpyrido[3,4-c]cinnolines. When evaluating the hypoglycemic properties of the four obtained β-carbolines, it was found that ethyl 7-fluoro-1,3-dimethyl-9H-pyrido[3,4-b]indole-4-carboxylate, the structure of which
contains the fluorine atom, has the highest glucose-lowering action.

Keywords


azidopyridine; Hantzsch nitropyridines; pyrido[3,4-c]cinnoline; 9H-pyrido[3,4-b]indole; azo coupling; Cadogan reaction; cyclization.

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