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

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Chemistry of Heterocyclic Compounds Aims and scope

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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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1848–1852, December, 2004.

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Glotova, T.E., Protsuk, N.I., Kanitskaya, L.V. et al. Reactions of α-acetylenic ketones with n-3-amidinothioureas. 1. Synthesis and properties of new derivatives of 1,3-thiazine. Chem Heterocycl Compd 40, 1595–1599 (2004). https://doi.org/10.1007/s10593-005-0103-x

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  • DOI: https://doi.org/10.1007/s10593-005-0103-x

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