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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 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).

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