Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core

• Autor(es): Sá, Marcus Mandolesi ; Ferreira, Misael ; Bortoluzzi, Adailton João ; Fernandes, Luciano Gonçalves ; Cunha, Silvio do Desterro ; Sá, Marcus Mandolesi ; Ferreira, Misael ; Bortoluzzi, Adailton João ; Fernandes, Luciano Gonçalves ; Cunha, Silvio do Desterro
• Data: 2013
• Origem: Oasisbr
• Assunto(s): 1,3-thiazinone; Allylic bromide; Aqueous solvent; Isothiuronium salt
• Tipo de Documento: Artigo científico
• Idioma: Inglês

Descrição

p.303-321

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Made available in DSpace on 2013-07-04T13:04:53Z (GMT). No. of bitstreams: 1 Marcus M. Sá.pdf: 477609 bytes, checksum: 7a03da5e6a1af957bcff9c8ea60a5303 (MD5) Previous issue date: 2010

The 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.