SYNTHESIS, HYDROLYSIS, AND REDUCTIVE CYCLIZATION OF ETHYL 5-CHLORO-4-(4-NITROPYRROLIDIN-3-YL)PYRROLE-3-CARBOXYLATES

Authors

  • Алина Н. Грозав Bukovinian State Medical University, 2 Teatral'na Sq., Chernivtsi 58000, Ukraine
  • Сергей B. Кемский Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094, Ukraine
  • Марьяна З. Федорив Ivano-Frankivsk National Medical University, 2 Halyts'ka St., Ivano-Frankivsk 76018, Ukraine
  • Виталий A. Чорноус Bukovinian State Medical University, 2 Teatral'na Sq., Chernivtsi 58000, Ukraine
  • Алина А. Паламар Bukovinian State Medical University, 2 Teatral'na Sq., Chernivtsi 58000, Ukraine
  • Виктор И. Дорохов Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094, Ukraine
  • Эдуард Б. Русанов Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094, Ukraine
  • Михаил B. Вовк Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094, Ukraine

DOI:

https://doi.org/10.1007/6497

Keywords:

4-(4-aminopyrrolidin-3-yl)-5-chloropyrrole-3-carboxylates, ethyl 5-chloro-4-(2-nitroethenyl)pyrrole-3-carboxylates, hexahydrodipyrrolo[3, 4-b, 3', 4'-d]pyridin-5(1H)-ones, N-methylazomethine ylide, cyclocondensation, hydrolysis.

Abstract

Ethyl 5-chloro-4-(2-nitroethenyl)pyrrole-3-carboxylates, obtained by the condensation of ethyl 5-chloro-4-formylpyrrole-3-carboxylates with nitromethane, react with N-methylazomethine ylide with the formation of ethyl 5-chloro-4-(4-nitropyrrolidin-3-yl)pyrrole-3-carboxylates. Their hydrolysis yielded the corresponding acids, while reductive cyclization led to the synthesis of hexahydrodipyrrolo-[3,4-b:3',4'-d]pyridin-5(1Н)-one via intermediate ethyl 4-(4-aminopyrrolidin-3-yl)-5-chloropyrrole-3-carboxylate derivatives.

Author Biography

Алина Н. Грозав, Bukovinian State Medical University, 2 Teatral'na Sq., Chernivtsi 58000, Ukraine

кандидат химических наук (органическая химия), доцент кафедры медицинской и фармацевтической химии

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Published

2022-01-27

Issue

Vol. 58 No. 1 (2022)

Section

Original Papers