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ARKIVOC - Online Journal of Organic Chemistry

By Marcus Mandolesi Sá, Misael Ferreira, Adailton J. Bortoluzzi, Luciano Fernandes and Silvio Cunha

Abstract

p.303-321The reactivity profile of allylic bromides (derived from the Morita-Baylis-Hillman reaction) towards thiourea derivatives and further transformations of the resulting isothiuronium bromides are described. Isothiuronium salts, prepared in near quantitative yields, undergo a selective acetylation or a base-promoted intramolecular cyclization to give 2-amino-1,3-thiazin-4-ones in good overall yields. Besides the simplicity of the reaction, conditions, and purification steps, the methods presented here furnished high-purity products. The structural characterization of representative compounds was unequivocally confirmed by X-ray diffraction analysis

Topics: 1,3-thiazinone, Allylic bromide, Aqueous solvent, Isothiuronium salt
Year: 2010
OAI identifier: oai:agregador.ibict.br.RI_UFBA:oai:192.168.11:11:ri/12096
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