<i>trans</i>-STEREOSELECTIVE REDUCTION OF HEXAHYDROQUINAZOLINE-2(1<i>H</i>)-THIONE DERIVATIVES

Authors

  • И. М. Гелла Scientific-Technological Complex "Institute of Monocrystals", National Academy of Sciences of Ukraine
  • О. Д. Буй V. N. Karazin Kharkiv National University
  • А. В. Мирный V. N. Karazin Kharkiv National University
  • С. В. Шишкина Scientific-Technological Complex "Institute of Monocrystals", National Academy of Sciences of Ukraine
  • О. В. Шишкин Scientific-Technological Complex "Institute of Monocrystals", National Academy of Sciences of Ukraine
  • В. Д. Орлов V. N. Karazin Kharkiv National University

DOI:

https://doi.org/10.1007/410

Keywords:

4-arylquinazoline-2(1H)-thiones, ketene dithioacetals, sodium borohydride, regioselective reduction

Abstract

Reduction of substituted 4-arylhexahydroquinazoline-2(1H)-thiones using NaBH4/CF3CO2H in chloroform gave the corresponding transfused octahydroquinazoline-2(1H)-thiones. The use of two reducing systems, NaBH4/CH3CO2H or NaBH4/CF3CO2H, permitted the consecutive transselective reduction of the endo- and exocyclic double bond in the case of 8-dithiomethylidene derivatives of hexahydroquinazoline-2(1H)-thiones.

Authors: I. M. Gella, O. D. Bui, A. V. Mirnyi, S. V. Shishkina, O. V. Shishkin, and V. D. Orlov

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (2), pp 302-309

http://link.springer.com/article/10.1007/s10593-013-1247-8

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Published

2013-03-18

Issue

No. 2 (2013)

Section

Original Papers