SYNTHESIS OF NEW HEXAHYDRO-5<i>H</i>-INDOLO[3,2-<i>c</i>]ACRIDINES AND INDOLYLBUTANOIC ACIDS BY FISCHER CYCLIZATION OF ARYLHYDRAZONES

Authors

  • Екатерина В. Зализная Ukrainian State University of Chemical Technology
  • Николай В. Сметанин Ukrainian State University of Chemical Technology
  • Светлана А. Варениченко Ukrainian State University of Chemical Technology
  • Александр В. Мазепа A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine
  • Олег К. Фарат Lomonosov Moscow State University
  • Виктор И. Марков Ukrainian State University of Chemical Technology

DOI:

https://doi.org/10.1007/4252

Keywords:

diazonium salt, octahydroacridines, substituted indoles, azo coupling, electrophilic substitution, Fischer reaction, Japp–Klingemann reaction

Abstract

Arylhydrazones of 2,3,5,6,7,8-hexahydroacridin-4(1H)-ones and 7-amino-6-(arylhydrazono)-7-oxoheptanoic acids were cyclized by Fischer reaction, providing previously unknown polysubstituted indole derivatives. The starting hydrazones were synthesized under Japp–Klingemann reaction conditions by using 1,2,3,4,5,6,7,8-octahydroacridine-4-carboxamide and 2-oxocyclohexanecarboxamide as starting materials. It was established from the spectral data that the obtained 7-amino-6-(arylhydrazono)-7-oxoheptanoic acids existed as mixtures of (Z)- and (E)-isomers, but were converted to an individual (Z)- or (E)-isomer in DMSO solution.

Author Biographies

Екатерина В. Зализная, Ukrainian State University of Chemical Technology

Екатерина Владимировна Зализная

ассистент кафедры технологии органических соединений и фармацевтических препаратов

Николай В. Сметанин, Ukrainian State University of Chemical Technology

Николай Викторович Сметанин

магистр кафедры технологии органических соединений и фармацевтических препаратов

Светлана А. Варениченко, Ukrainian State University of Chemical Technology

Светлана Анатольевна Варениченко

к.х.н., доцент кафедры технологии органических соединений и фармацевтических препаратов

Александр В. Мазепа, A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine

к.х.н, научный сотрудник

Олег К. Фарат, Lomonosov Moscow State University

Олег Константинович Фарат

к.х.н, научный сотрудник химического факультета

Виктор И. Марков, Ukrainian State University of Chemical Technology

Виктор Иванович Марков

д.х.н., профессор кафедры технологии органических соединений и фармацевтических препаратов

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Published

2018-03-23

Issue

Vol. 54 No. 2 (2018)

Section

Original Papers