Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from 2-iodophenylcinnamamides and potassium sulfide. Issue 46 (21st November 2017)

• Record Type: Journal Article
• Authors: Liu, Wenjuan; Min, Hao; Zhu, Xiaoming; Deng, Guobo; Liang, Yun
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 46(2017)
• Page Start: 9804
• Page End: 9808
• Publication Date: 2017-11-21
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02585h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : DBU as a switch could control the selectivity of the formation of 2-benzyl-substituted benzo[ b ]thiazinones and 2-benzylidenebenzo[ b ]thiazinones. Abstract : An efficient and practical procedure for the synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[ b ]thiazinones from easily available 2-iodophenylcinnamamides and potassium sulfide has been developed. In the presence of DBU, the reaction proceeds via electrophilic addition, followed by dehydrogenation and reduction to give 2-benzyl benzo[ b ]thiazinones. Furthermore, 2-benzylidenebenzo[ b ]thiazinones were obtained in moderate to good yields without the addition of DBU.