The Synthesis of Multisubstituted Pyrroles via a Copper-Catalyzed Tandem Three-Component Reaction.

Org Lett

School of Pharmacy and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.

Published: August 2016

An unprecedented nucleophilic addition/cyclization/aromatization cascade of basic chemicals, i.e., aromatic alkenes/alkynes, trimethylsilyl cyanide and N,N-disubstituted formamide, has been developed to give a series of multisubstituted pyrroles in moderate to good yields with high regioselectivities. This reaction not only reveals a new reaction mode for α-aminonitriles, but also provides a new and efficient cyclization pattern for the synthesis of multisubstituted pyrroles as well as their derivatives, which might facilitate related biological studies.

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http://dx.doi.org/10.1021/acs.orglett.6b01883DOI Listing

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