Synthesis of Benzo[<i>e</i>][1,4]thiazepines by Base-Induced Formal [4+3] Annulation Reaction of Aza-<i>o</i>-quinone Methides and Pyridinium 1,4-Zwitterionic Thiolates
Lijie Zhang, Ling Fang, Hao Huang, Chaofan Wang, Fang Gao, Zhiyong Wang
Abstract
The base-induced formal [4+3] annulation reaction of in situ-formed aza-o-quinone methides and pyridinium 1,4-zwitterionic thiolates is reported. This protocol provides a novel and reliable method for the synthesis of biologically interesting benzo[e][1,4]thiazepine derivatives in synthetically useful yields. In addition, postsynthetic modification results in the formation of its sulfoxide and sulfone derivatives.
Topics & Concepts
AnnulationChemistryPyridiniumSulfoneSulfoxideQuinoneBase (topology)Combinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryCatalysisMathematical analysisMathematicsSulfur-Based Synthesis TechniquesSynthesis of Indole DerivativesChemical Synthesis and Reactions