An efficient regioselective synthesis of 4-iodo-2,3-disubstituted-2H-thieno[3,2-e][1,2]thiazine-1,1-dioxide derivatives via iodocyclization approach using iodine under mild reaction condition described herein. This coupling-iodocyclization strategy tolerated a variety of functional groups such as alkyl, cycloalkyl, phenyl producing the six-membered heterocyclic ring selectively. The resulting 4-iodo-2,3-disubstituted-2H-thieno[3,2-e][1,2]thiazine-1,1-dioxide was coupled with a variety of boronic acids (Suzuki coupling) and activated alkenes (Heck coupling). The iodo group was utilized for Sonogashira coupling followed by efficient transformation to azido precursor, which was used for the synthesis of various thieno-sultam linked with triazole.
- Fused sultam
- Regioselective synthesis
- Sonogashira, Heck and Suzuki coupling
- Triazole linker
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
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Barange, D. K. (Creator), Kavala, V. (Creator), Kuo, C. (Creator), Wang, C. (Creator), Rajawinslin, R. R. (Creator), Donala, J. (Creator) & Yao, C. (Creator), Unknown Publisher, 2015