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Efficient approach to 4-sulfonamidoquinolines via copper(I)-catalyzed cascade reaction of sulfonyl azides with alkynyl imines.

Organic letters (2013-03-26)
Guolin Cheng, Xiuling Cui
RÉSUMÉ

A novel and efficient approach to 4-sulfonamidoquinolines via copper-catalyzed cascade reaction of sulfonyl azides with alkynyl imines has been developed in which a 1,3-dipole cycloaddition/ketenimine formation/6π-electrocyclization/[1,3]-H shift cascade reaction was involved. Various 4-sulfonamidoquinolines were afforded in up to 84% yield for 19 examples. This synthetic strategy features with atom economy, concise steps, easy operation, and mild reaction conditions.

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Sigma-Aldrich
Copper(I) iodide, 98%
Sigma-Aldrich
Copper(I) iodide, 99.999% trace metals basis
Sigma-Aldrich
Copper(I) iodide, purum, ≥99.5%