Organic & biomolecular chemistry

Brønsted acid catalyzed intramolecular benzylic cyclizations of alkylpyridines

AI Lansakara, DP Farrell, FC Pigge

Index: Lansakara, Ashabha I.; Farrell, Daniel P.; Pigge, F. Christopher Organic and Biomolecular Chemistry, 2014 , vol. 12, # 7 p. 1090 - 1099

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Citation Number: 11

Abstract

Aldehyde and ketone electrophiles incorporated into the side chains of 2-and 4- alkylpyridines participate in intramolecular aldol-like condensations with pyridine benzylic carbons in the presence of Brønsted acid catalysts. Pyridines featuring β-ketoamide side chains undergo cyclization in the presence of 10 mol% TfOH to afford pyridyl-substituted hydroxy lactams in good yield. These products were found to be resistant to further ...