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Potential Acyl-transfer Agents. Reactions of N-Acyl-2-pyridinecarboxamides with Nucleophiles
Morkved, Eva H.,Cronyn, Marshall W.
, p. 381 - 388 (2007/10/02)
A fast reaction is obserwed between a series of N-acyl-2-pyridinecarboxamides and cyclopentylamine or pyrrolidine.Most of the acylamides react exclusively at the pyridine-2-carbonyl group.The selectivity of these reactions is explained by the reaction of the pyridine-nitrogen as a base towards the external nucleophile in a five-ring transition state.The acylamides undergo slow reactions with 4-methylaniline, methanol or water.Several reaction paths are observed with these less reactive nucleophiles.An intramolecular acyl group transfer prior to the reaction with an external nucleophile is indicated for three of the N-acylamides which have an N,N-dialkylamino substituent in the pyridine-4-position.Nucleophilic attack occurs predominantly at the N-acyl group of these three compounds which are moderately active acyl-transfer agents.
