SYNTHESIS OF 4-NITRO-γ-CARBOLINES BY GRAEBE–ULLMANN REACTION

Authors

  • Владислав Ю. Шувалов Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia
  • Александр Н. Шестаков F. M. Dostoyevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia
  • Людмила А. Кулакова F. M. Dostoyevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia
  • Анна К. Куратова F. M. Dostoyevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia
  • Марина А. Воронцова F. M. Dostoyevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia
  • Галина П. Сагитуллина F. M. Dostoyevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia

DOI:

https://doi.org/10.1007/4971

Keywords:

4-amino-3-nitropyridines, 1-[6-aryl(methyl)-2-methyl(cyclopropyl)-3-nitropyridin-4-yl]-1Н-1, 2, 3-benzotriazoles, 3-aryl(methyl)- 1-methyl(cyclopropyl)-4-nitro-5Н-pyrido[4, 3-b]indoles, 4-chloro-3-nitropyridines, ethyl (4-pyridyl)carbamates, ethyl esters and amides of 3-nitroisonicotinic acid, Graebe–Ullmann reaction.

Abstract

Graebe–Ullmann reaction was used to synthesize 3-aryl(methyl)-1-methyl(cyclopropyl)-4-nitro-5Н-pyrido[4,3-b]indoles containing substituents in the pyridine ring. A new scheme was developed for the synthesis of the starting 1-[6-aryl(methyl)-2-methyl(cyclopropyl)-3-nitropyridin-4-yl]-1Н-1,2,3-benzotriazoles: 1) ammonolysis of 3-nitroisonicotinic acid ethyl esters, 2) a modified Hofmann reaction of 3-nitroisonicotinamides, 3) cleavage of ethyl (2-aryl-3-nitropyridin-4-yl)carbamates, 4) synthesis of 4-chloro-3-nitropyridines by diazotation reaction of 4-amino-3-nitropyridines, followed by nucleophilic substitution of diazo group in 4-pyridyldiazonium salts with a
chlorine atom.

Author Biography

Галина П. Сагитуллина, F. M. Dostoyevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia

доцент кафедры органической химии, к.х.н.

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Published

2019-09-17

Issue

Vol. 55 No. 9 (2019)

Section

Original Papers