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

Authors

  • Виктория A. Прощенкова Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia
  • Владислав Ю. Шувалов Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia
  • Лариса В. Глиздинская Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia
  • Александр С. Фисюк Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia
  • Сергей А. Черненко Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia
  • Михаил В. Хвостов N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
  • Татьяна Г. Толстикова N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
  • Марина А. Воронцова Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia
  • Галина П. Сагитуллина Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

DOI:

https://doi.org/10.1007/5966

Keywords:

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

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.

Author Biographies

Лариса В. Глиздинская, Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

доцент кафедры органической химии, к.х.н.

Александр С. Фисюк, Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia

профессор, доктор химических наук, профессор кафедры органической химии, заведующий кафеды органической химии ОмГУ им. Ф. М. Достоевского

Михаил В. Хвостов, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia

д.б.н.

Татьяна Г. Толстикова, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia

д.б.н., профессор

Марина А. Воронцова, Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

доцент кафедры органической химии, к.х.н.

Галина П. Сагитуллина, Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

доцент кафедры органической химии, к.х.н.

Downloads

Published

2021-02-23

Issue

Vol. 57 No. 2 (2021)

Section

Original Papers