Synthesis of 1-Aminoisoquinolines via the Coinage Metal Cocatalyzed Reaction of 2-Alkynylbenzaldoximes with Isocyanoacetates

Abstract

An efficient reaction of 2-alkynylbenzaldoximes with 2-isocyanoacetates cocatalyzed by silver triflate and gold(I) chloride is described, providing 1-aminoisoquinolines in good to excellent yields under mild conditions. Mechanistic experiments suggest that the gold(I) cation might play a crucial role in the activation of the isocyanide substrate. The observed reactivity and the unique pathway of substrate activation in the cocatalyzed processes are quite informative for further study.

Key words

1-aminoisoquinolines - coinage metals - deformylation - 2-alkynylbenzaldoximes - isocyanoacetates

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