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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.

ABSTRACT: 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 ?-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).

SUBMITTER: Vorob'ev AY

PROVIDER: S-EPMC5433178 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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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.

Vorob'ev Aleksey Yu AY Supranovich Vyacheslav I VI Borodkin Gennady I GI Shubin Vyacheslav G VG

Beilstein journal of organic chemistry 20170502

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 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). ...[more]

PMID: 28546837

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