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Molecules 2005, 10(9), 1109-1118; doi:10.3390/10091109
Article

Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines

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Received: 23 April 2005 / Accepted: 1 September 2005 / Published: 1 September 2005
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Abstract

A series of previously unavailable derivatives of 2-alkyl- and 2-benzylderivatives of oxazolo[3,2-a]pyridines III were obtained via tandem ring opening and ring closure from stable mesoionic 3-acyloxazolo[3,2-a]pyridinium-2-olates I. The key intermediates of this tandem transformation are N-(b-oxoethyl)pyridones-2 II obtained by Dakin-West acylation of (pyridone-2-yl-1)acetic acid. An example of further utilization of this strategy is illustrated by preparation of unknown 2-benzylimidazo[1,2-a]pyridine from the salt I and ammonia.
Keywords: Oxazolo[3; 2-a]pyridinium salts; mesoionic oxazolo[3; 2-a]pyridinium-2-olates; munchnones; recyclization; hydrolytical cleavage of oxazolone; Dakin-West reaction Oxazolo[3; 2-a]pyridinium salts; mesoionic oxazolo[3; 2-a]pyridinium-2-olates; munchnones; recyclization; hydrolytical cleavage of oxazolone; Dakin-West reaction
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Kazhkenov, Z.-G.M.; Bush, A.A.; Babaev, E.V. Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines. Molecules 2005, 10, 1109-1118.

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