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New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines

An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D(2)O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivit...

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Detalles Bibliográficos
Autores principales: Vorob’ev, Aleksey Yu, Supranovich, Vyacheslav I, Borodkin, Gennady I, Shubin, Vyacheslav G
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433178/
https://www.ncbi.nlm.nih.gov/pubmed/28546837
http://dx.doi.org/10.3762/bjoc.13.80
Descripción
Sumario:An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D(2)O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivity and a high degree of deuterium incorporation were achieved. The procedure was applied for several 4-R-1-aminopyridinium cations (R = H, Me, OMe).