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

Author: Glotova T.   Protsuk N.   Kanitskaya L.   Dolgushin G.   Lopyrev V.  

Publisher: Springer Publishing Company

ISSN: 0009-3122

Source: Chemistry of Heterocyclic Compounds, Vol.40, Iss.12, 2004-12, pp. : 1595-1599

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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⋅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.

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