F. Palacios et al., A NEW AND EFFICIENT SYNTHESIS OF IMIDAZO[1,5-A]PYRIDINE DERIVATIVES BY A TANDEM AZA-WITTIG ELECTROCYCLIC RING-CLOSURE OF N-VINYLIC PHOSPHAZENES, Tetrahedron, 51(12), 1995, pp. 3683-3690
Imidazo[1,5-a]pyridines 1 are prepared by reaction of N-vinylic phosph
azene 3, obtained from phosphorus ylide 5 and 2-cyanopyridine 4, with
aldehydes. Formation of fused heterocycles 1 can be explained through
aza-Wittig reaction of phosphazene 3, followed by 1,5-electrocyclic ri
ng closure of the resulting aldimines 2. Phosphazene 3 undergoes pyrid
o annelation by reaction with Diethyl Ketomalonate to give isoquinolin
e derivative 9.