Reactions of -acetylenic ketones with n-3-amidinothioureas. 1. Synthesis and properties of new derivatives of 1,3-thiazine

Authors: Glotova, T.¹; Protsuk, N.²; Kanitskaya, L.²; Dolgushin, G.²; Lopyrev, V.²

Source: Chemistry of Heterocyclic Compounds, Volume 40, Number 12, December 2004 , pp. 1595-1599(5)

Publisher: Springer

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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 sdot

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.

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

Document Type: Research article

DOI: http://dx.doi.org/10.1007/s10593-005-0103-x

Affiliations: 1: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033, Irkutsk, Email: k301@irioch.irk.ru 2: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033, Irkutsk,

Publication date: 2004-12-01