Sulfuryl chloride promoted gem-dichlorination-dehydrochlorination in alkyl benzothiazinylacetates: synthesis of the skeleton of trichochrome pigments

TitleSulfuryl chloride promoted gem-dichlorination-dehydrochlorination in alkyl benzothiazinylacetates: synthesis of the skeleton of trichochrome pigments
Publication TypeJournal Article
Year of Publication2015
AuthorsJangir, R, Gadre, SR, Argade, NP
JournalSynthesis-Stuttgart
Volume47
Issue17
Pagination2631-2634
Date PublishedSEP
ISSN0039-7881
Keywordscondensations, halogenation, maleic anhydride, o-aminothiophenol, trichochrome framework
Abstract

Chemo- and stereoselective total synthesis of the basic trichochrome skeleton is described starting from o-aminothiophenol and maleic anhydride in very good overall yield. The process involves the synthesis of the corresponding 1,4-benzothiazin-2-ylacetates followed by their sulfuryl chloride induced dihalogenation-dehydrohalogenation and a second condensation with o-aminothiophenol as key steps.

DOI10.1055/s-0034-1378714
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.652
Divison category: 
Organic Chemistry