NEW APPROACH TO THE SYNTHESIS OF 1,3-CHLOROISOTHIOCYANATOALKANES. SYNTHESIS OF TETRAHYDRO-1,3-THIAZINE-2-THIONES AND 2-ALKYLAMINO-5,6-DIHYDRO-1,3-THIAZINES

Authors

  • А. С. Фисюк Omsk State University, Omsk 644077
  • Н. В. Перетокин Omsk State University, Omsk 644077
  • Б. В. Унковский Omsk State University, Omsk 644077

Keywords:

2-amino-5,6-dihydro-1,3-thiazines, 1,3-isothiocyanato ketones, 1,3-isothiocyanato alcohols, tetrahydro-1,3-thiazine-2-thiones, 1,3-chloroisothiocyanatoalkanes, intramolecular cyclization

Abstract

A method was developed to prepare 1,3-chloroisothiocyanatoalkanes by reducing 1,3-isothiocyanato ketones using sodium borohydride at pH ~7 and subsequent treatment of the resultant 1,3-isothiocyanato alcohols with thionyl chloride. The reaction of 1,3-chloroisothiocyanatoalkanes with sodium hydrosulfide or amines gives substituted tetrahydro-1,3-thiazine-2-thiones or 2-amino-5,6-dihydro-1,3-thiazines.

How to Cite
Fisyuk, A. S.; Peretokin, N. V.; Unkovsky, B. V. Chem. Heterocycl. Compd. 2003, 39, 802. [Khim. Geterotsikl. Soedin. 2003, 930.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1025663616439

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Published

2003-06-25

Issue

No. 6 (2003)

Section

Original Papers