Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction

The simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of S-vinyl phosphorodithioate with thiotosylates or S-vinyl thiotosylate with thiols. The designed methods allow for the synthesis of unsymmetrical vinyl disulfides with additional functionalities such as hydroxy, carboxy, protected amino, or ester groups. Vinyl disulfides reacted with the generated transient o-iminothioquinones in an inverse electron-demand [4+2] cycloaddition to produce benzo[b][1,4]thiazine derivatives.

Automated summary

The study has developed simple and efficient methods for the synthesis of unsymmetrical vinyl disulfides with additional functional groups under mild conditions. These methods involve reactions between S-vinyl phosphorodithioate and thiotosylates, allowing for the synthesis of vinyl disulfides with various additional functionalities. Furthermore, the vinyl disulfides react with transient o-iminothioquinones in an inverse electron-demand [4+2] cycloaddition to yield benzo[b][1,4]thiazine derivatives.