Metal-Free [2 + 2 + 2] Cycloaddition of Ynamide-Nitriles with Ynamides: A Highly Regio- and Chemoselective Synthesis of δ-Carboline Derivatives

J Org Chem. 2018 Nov 2;83(21):13308-13324. doi: 10.1021/acs.joc.8b02112. Epub 2018 Oct 24.

Abstract

A metal-free formal [2 + 2 + 2] cycloaddition of functionalized ynamide-nitriles with ynamides is disclosed which offers highly efficient access to polysubstituted δ-carboline derivatives under the mediation of TfOH. This strategy is highly regioselective and chemoselective and displays mild conditions, high yields, and efficiency (within 1 min) in addition to substrates scopes (56 examples).