Synthesis of N‐Bridged 6,8‐Dinitrotriazolo[1,5‐a]pyridines

This is the authors' abstract. We don't add key points for this paper.

Facile and efficient protocols for the synthesis of 2‐R‐6,8‐dinitro[1,2,4]triazolo[1,5‐a]pyridines from commercially available starting materials have been developed. The reactions proceed via cyclization of corresponding 3,5‐dinitropyridine‐2‐yl hydrazides or aldehyde 3,5‐dinitropyridine‐2‐yl hydrazones followed by in situ Dimroth rearrangement to provide these triazole fused bicyclic heterocycles in good yields under mild conditions. Another synthetic route to target N‐bridged dinitro[1,2,4]triazolo[1,5‐a]pyridines includes arylation of 5‐aryltetrazoles with 2‐chloro‐3,5‐dinitropyridine and subsequent thermal decomposition/cyclization.