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https://repositorio.ufba.br/handle/ri/12096
metadata.dc.type: | Artigo de Periódico |
Title: | 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 |
Other Titles: | ARKIVOC - Online Journal of Organic Chemistry |
Authors: | Sá, Marcus Mandolesi Ferreira, Misael Bortoluzzi, Adailton João Fernandes, Luciano Gonçalves Cunha, Silvio do Desterro |
metadata.dc.creator: | Sá, Marcus Mandolesi Ferreira, Misael Bortoluzzi, Adailton João Fernandes, Luciano Gonçalves Cunha, Silvio do Desterro |
Abstract: | 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. |
Keywords: | 1,3-thiazinone Allylic bromide Aqueous solvent Isothiuronium salt |
URI: | http://www.repositorio.ufba.br/ri/handle/ri/12096 |
Issue Date: | 2010 |
Appears in Collections: | Artigo Publicado em Periódico (Química) |
Files in This Item:
File | Description | Size | Format | |
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Marcus M. Sá.pdf | 466,42 kB | Adobe PDF | View/Open |
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