Highly regioselective assembly of Di- or trisubstituted pyridines from arynes, isocyanides, and 3-bromo- or 3-acetoxypropynes

Abstract

A facile synthetic method for the preparation of di- and trisubstituted pyridines with high regioselectivity through an intramolecular pericyclization strategy is disclosed. The multicomponent reaction of isocyanides, arynes, and 3-bromopropyne affords disubstituted pyridines in good yields. In contrast, the use of 3-acetoxypropyne results in the formation of trisubstituted pyridines through intramolecular pericyclization of an in situ formed azatriene. In this way, desirable pyridines can be constructed in a one-pot manner. The preparation of di- or trisubstituted pyridines with high regioselectivity through the multicomponent reaction of isocyanides, arynes, and 3-bromo or 3-acetoxypropyne is described. The pyridine ring is constructed through intramolecular pericyclization of an in situ generated azatriene intermediate. The pyridine products are assembled effectively in a one-pot manner under mild conditions. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.