Thiazoles via Formal [4 + 1] of NaSH to (Z)-Bromoisocyanoalkenes

噻唑通过NaSH的[4+1]形式反应生成(Z)-溴异氰基烯烃

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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(N)V(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.

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