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Note | Regular issue | Vol 53, No. 8, 2000, pp.1793-1805
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8925
Synthesis of Alkyl 1-(Substituted Pyridin-2-yl)-1H-1,2,3-triazole-4-carboxylates by ‘Ring Switching’ Transformation of 4-Oxo-4H-pyridino[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates

Simon Recnik, Jurij Svete,* Anton Meden, and Branko Stanovnik*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, 1000 Ljubljana, Slovenia

Abstract

Substituted 3-amino-4-oxo-4H-pyridino[1,2-a]pyrimidines (6, 7), available in 2 steps from methyl 2-benzyloxycarbonylamino-3-dimethylaminopropenoate (3) and 2-aminopyridines (1, 2), were diazotized into stable diazonium tetrafluoroborates (8, 9). Heating of diazonium salts (8, 9) with primary alcohols furnished alkyl 1-(substituted pyridin-2-yl)-1H-1,2,3-triazoles (11, 12) in 30-70% yields.