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

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

Journal

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Output data

Year: 2017, Volume: 13, Pages: 800-805 Pages count : 6 DOI: 10.3762/bjoc.13.80

Tags

deuteration; 1,3-dipolar cycloaddition; pyrazolo[1,5-a]pyridine; 1,2,4-triazolo[1,5-a]pyridine

Authors

Vorob'ev Aleksey Yu. ^1,2 , Supranovich Vyacheslav I. ^1,2 , Borodkin Gennady I. ^1,2 , Shubin Vyacheslav G. ¹

Affiliations

1	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Acad Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogov St 2, Novosibirsk 630090, Russia

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 alpha-H/D exchange of 1-aminopyridinium cations in basic D2O 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).

Vorob'ev A.Y. , Supranovich V.I. , Borodkin G.I. , Shubin V.G.
New approach toward the synthesis of deuterated pyrazolo[1,5-a] pyridines and 1,2,4-triazolo[1,5-a] pyridines

Beilstein Journal of Organic Chemistry. 2017. V.13. P.800-805. DOI: 10.3762/bjoc.13.80 WOS Scopus РИНЦ

Full text from publisher

Published online:

May 2, 2017

Web of science	WOS:000407579500001
Scopus	2-s2.0-85020773061
Elibrary	31022564
OpenAlex	W2610452384