Thiazoles via Formal [4 + 1] of NaSH to (<i>Z</i>)-Bromoisocyanoalkenes.

ABSTRACT: A formal [4 + 1] addition of NaSH to bromoisocyanoalkenes provides substituted thiazoles via a versatile strategy that affords an array of 4- or 5-monosubstituted or 4,5-disubstituted thiazoles. The unique assembly is achieved by a rare S_NV_π displacement of NaSH on (Z)-bromoisocyanoalkenes. The versatile strategy addresses the dearth of conjugate additions to alkenes substituted with isocyanides as the sole electron-withdrawing group to provide an array of substituted thiazoles.

SUBMITTER: Tian H 

PROVIDER: S-EPMC11976862 | biostudies-literature | 2025 Apr

REPOSITORIES: biostudies-literature