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

doi:10.3390/10091109

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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

Zeinul-Gabiden M. Kazhkenov, Alexander A. Bush and Eugene V. Babaev *

Chemistry Department, Moscow State University, Moscow 119992, Russia

* Author to whom correspondence should be addressed.

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

(This article belongs to the Special Issue Selected Papers from the “2nd International Conference on Natural Products and Physiologically Active Substances” (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry”)

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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

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MDPI and ACS Style

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.

AMA Style

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(9):1109-1118.

Chicago/Turabian Style

Kazhkenov, Zeinul-Gabiden M.; Bush, Alexander A.; Babaev, Eugene V. 2005. "Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines." Molecules 10, no. 9: 1109-1118.

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