1H-imidazo[4,5-c]quinoline-1,2-diamine → [1,2,4]Triazolo[1',5':1,2]imidazo[4,5-c]quinoline

Participants

Reaction Steps

In step (2) of Reaction Scheme VIII, a 1H-imidazo[4,5-c]quinoline-1,2-diamine or 1H-imidazo[4,5-c][1,5]naphthyridine-1,2-diamine of Formula LXVI is treated with an ortho ester of Formula R2aC(O-alkyl)3 to provide a [1,2,4]triazolo[1′,5′:1,2]imidazo[4,5-c]quinoline or [1,2,4]triazolo[1′,5′:1,2]imidazo[4,5-c][1,5]naphthyridine of Formula LXVII. The reaction can be carried out by adding the ortho ester to a compound of Formula LXVI in a suitable solvent such as toluene. The reaction is carried out at a temperature high enough to drive off alcohol formed during the reaction; a Dean-Stark trap can be used to collect the volatiles.

Provenance & Evidence