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

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-oxoet...

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Autores principales: Kazhkenov, Zeinul-Gabiden M., Bush, Alexander A., Babaev, Eugene V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2005
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147565/
https://www.ncbi.nlm.nih.gov/pubmed/18007376
http://dx.doi.org/10.3390/10091109
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author Kazhkenov, Zeinul-Gabiden M.
Bush, Alexander A.
Babaev, Eugene V.
author_facet Kazhkenov, Zeinul-Gabiden M.
Bush, Alexander A.
Babaev, Eugene V.
author_sort Kazhkenov, Zeinul-Gabiden M.
collection PubMed
description 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.
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spelling pubmed-61475652018-11-19 Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines Kazhkenov, Zeinul-Gabiden M. Bush, Alexander A. Babaev, Eugene V. Molecules Article 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. MDPI 2005-09-30 /pmc/articles/PMC6147565/ /pubmed/18007376 http://dx.doi.org/10.3390/10091109 Text en © 2005 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Kazhkenov, Zeinul-Gabiden M.
Bush, Alexander A.
Babaev, Eugene V.
Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
title Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
title_full Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
title_fullStr Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
title_full_unstemmed Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
title_short Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
title_sort dakin-west trick in the design of novel 2-alkyl(aralkyl) derivatives of oxazolo[3,2-a]pyridines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147565/
https://www.ncbi.nlm.nih.gov/pubmed/18007376
http://dx.doi.org/10.3390/10091109
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