A synthesis of N-bridged 5,6-bicylic pyridines via a mild cyclodehydration using the burgess reagent and discovery of a novel carbamylsulfonylation reaction.

ABSTRACT

Cyclodehydration using the Burgess reagent provided a novel approach toward the synthesis of N-bridged 5,6-bicylic pyridines including pyrolo-, imidazo-, and triazolopyridines under mild and neutral conditions. The methodology tolerates acid-sensitive functional groups. A novel addition product was observed between the resulting pyrrolo- or imidazopyridine and an additional equivalent of the Burgess reagent, producing the corresponding sulfonylcarbamate adduct.