SYNTHESIS OF 2-HETARYL-2-(TETRAHYDROFURAN-2-YLIDENE)ACETONITRILES

Authors

  • О. В. Хиля Taras Shevchenko Kyiv National University
  • Т. А. Воловненко Taras Shevchenko Kyiv National University
  • А. В. Туров Taras Shevchenko Kyiv National University
  • Р. И. Зубатюк Institute for Single Crystals
  • О. В. Шишкин Institute for Single Crystals
  • Ю. М. Воловенко Taras Shevchenko Kyiv National University

DOI:

https://doi.org/10.1007/1398

Keywords:

benzimidazolylacetonitrile, 2-(1-R-benzimidazol-2-yl)-2-(tetrahydrofuran-2-ylidene)acetonitrile, benzothiazolylacetonitrile, 2-(1, 3-benzothiazol-2-ylidene)-6-chloro-3-oxohexanenitrile, 3-benzothiazol-2-yl)-2-(tetrahydrofuran-2-ylidene)acetonitrile, 6-chloro-2-(1-R-1, 3-dihydro-2H-benzimidazol-2-ylidene)-3-oxo-hexanenitrile, 6-chloro-2-(4-methylthiazol-2-ylidene)-3-oxohexanenitrile, 2-(4-methyl-thiazol-2-yl)-2-(tetrahydrofuran-2-ylidene)acetonitrile, 4-oxo-3, 4-dihydroquinazolylacetonitrile

Abstract

The reaction of azolylacetonitriles with γ-chlorobutyryl chlorides gave the corresponding 2-(1-R-1,3-dihydro-2H-benzimidazol-2-ylidene)-, 2-(1,3-benzothiazol-2-ylidene)-, and 6-chloro-2-(4-methylthiazol-2-ylidene)-3-oxohexanenitriles. A study of the intramolecular cyclization of 2-(quinazolin-2-ylidene)-3-oxo-6-hexanenitriles and -heptanenitriles has led to the development of an efficient method for the preparation of 2-(quinazolin-2-yl)-2-(tetrahydrofuran-2-ylidene)acetonitriles. The (Z,E)-isomerism of the synthesized 2-hetaryl-2-(tetrahydrofuran-2-ylidene)acetonitriles was studied.

Authors: O. V. Khilya, T. A. Volovnenko, A. V. Turov, R. I. Zubatyuk, O. V. Shishkin, and Yu. M. Volovenko.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (9), pp 1141-1154

http://link.springer.com/article/10.1007/s10593-011-0885-y

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Published

2013-12-17

Issue

No. 9 (2011)

Section

Original Papers