An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-]pyridine and 7-deutero-1,2,4-triazolo[1,5-]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic DO 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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433178PMC
http://dx.doi.org/10.3762/bjoc.13.80DOI Listing

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