Beilstein Journal of Organic Chemistry (May 2017)

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

  • Aleksey Yu. Vorob’ev,
  • Vyacheslav I. Supranovich,
  • Gennady I. Borodkin,
  • Vyacheslav G. Shubin

DOI
https://doi.org/10.3762/bjoc.13.80
Journal volume & issue
Vol. 13, no. 1
pp. 800 – 805

Abstract

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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).

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