Nitrous oxide as a diazo transfer reagent: the synthesis of triazolopyridines

Nitrous oxide is a potential diazo transfer reagent, but its applications in organic chemistry are scarce. Here, we show that triazolopyridines and triazoloquinolines are formed in the reactions of metallated 2-alkylpyridines or 2-alkylquinolines with N 2 O. The reactions can be performed under mild conditions and give synthetically interesting triazoles in moderate to good yields. Nitrous oxide (N 2 O, 'laughing gas') can be used as diazo transfer reagent for the synthesis of triazolopyridines.