REACTIONS OF α-ACETYLENIC KETONES WITH N-3-AMIDINOTHIOUREAS. 1. SYNTHESIS AND PROPERTIES OF NEW DERIVATIVES OF 1,3-THIAZINE

Authors

  • Т. Е. Глотова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033
  • Н. И. Процук A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033
  • Л. В. Каницкая A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033
  • Г. В. Долгушин A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033
  • В. А. Лопырев A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033

DOI:

https://doi.org/10.1007/8428

Keywords:

N-amidinothiourea, benzoylacetylene, 4-phenyl-1, 2-dihydropyrimidine-2-thione, [4-phenyl-2H-1, 3-thiazin]-2-ylideneguanidinium perchlorate and acetoxytrifluoroborate, heterocyclization

Abstract

[4-Phenyl-2H-1,3-thiazin]-2-ylideneguanidinium perchlorate or acetoxytrifluoroborate respectively was obtained from the reaction of benzoylacetylene with N-amidinothiourea in glacial AcOH in the presence of an equimolar quantity of HClO4 or BF3·Et2O. These compounds underwent hydrolysis at the amidine unit on treatment with acid or base. For  example, the perchlorate on heating in HClO4 was converted into 2-imino-4-phenyl-2H-1,3-thiazinium perchlorate, while treatment with aqueous NaOH in DMSO gave the free base – 6-phenyl-1,2-dihydropyrimidine-2-thione.

How to Cite
Glotova, T. E.; Protsuk, N. I.; Kanitskaya, L. V.; Dolgushin, G. V.; Lopyrev, V. A.  Chem. Heterocycl. Compd. 2004, 40, 1595. [Khim. Geterotsikl. Soedin. 2004, 1848.]

For this article in the English edition, see DOI 10.1007/s10593-005-0103-x


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Published

2023-12-13

Issue

No. 12 (2004)

Section

Original Papers