INTERACTION OF 2-CHLOROQUINOLINE-3-CARBALDEHYDES WITH 2-HETARYLACETONITRILES

Authors

  • Т. А. Воловненко Kiev T. Shevchenko National University, Chemical Faculty, Department of Organic Chemistry, Kiev 01601
  • А. В. Тарасов Kiev T. Shevchenko National University, Chemical Faculty, Department of Organic Chemistry, Kiev 01601
  • Р. И. Зубатюк Scientific and Technological Corporation, Institute for Single Crystals, National Academy of Sciences of Ukraine, Kharkiv 61001
  • О. В. Шишкин Scientific and Technological Corporation, Institute for Single Crystals, National Academy of Sciences of Ukraine, Kharkiv 61001
  • А. В. Туров Kiev T. Shevchenko National University, Chemical Faculty, Department of Organic Chemistry, Kiev 01601
  • Ю. М. Воловенко Kiev T. Shevchenko National University, Chemical Faculty, Department of Organic Chemistry, Kiev 01601

DOI:

https://doi.org/10.1007/6235

Keywords:

(1-benzyl-1H-imidazol-2-yl)acetonitrile, 2-(1-benzyl-1H-imidazol-2-yl)-3-(2-chloroquinolin-3-yl)acrylonitrile, benzimidazo[1, 2-a]benzo[g]-1, 8-naphthyridine-6-carbonitriles, 1H-benzimidazol-2 ylacetonitriles, benzo[g]imidazo[1, 2-a]-1, 8-naphthyridine-4-carbonitriles, 2-(1H-benzimidazol-2-yl)-3-(2-chloroquinolin-3-yl)acrylonitriles, 5-alkyl-6-cyanobenzimidazo[1, 8-naphthyridinium chlorides, 2-chloroquinoline-3-carbaldehydes

Abstract

The interaction of 2-chloroquinoline-3-carbaldehydes with 1H-benzimidazol-2-ylacetonitriles and 1‑benzyl-1H-imidazol-2-ylacetonitrile has been studied. It was shown that products of condensation at the methylene group are formed under mild conditions. Carrying out the reaction under more forcing conditions leads to an intramolecular nucleophilic substitution of the chlorine atom and the formation of cyclic ionic compounds (in the case of N-substituted hetarylacetonitriles), which are subsequently dealkylated.

How to Cite
Volovnenko, T. A.; Tarasov, A. V.; Zubatyuk, R. I.; Shishkin, O. V.; Turov,  A. V.; Volovenko, Yu. M. Chem. Heterocycl. Compd. 2009, 45, 1489. [Khim. Geterotsikl. Soedin. 2010, 1847.]

For this article in the English edition see DOI 10.1007/s10593-010-0456-7

 

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Published

2021-03-26

Issue

No. 12 (2009)

Section

Original Papers