A NEW AND EFFICIENT SYNTHESIS OF IMIDAZO[1,5-A]PYRIDINE DERIVATIVES BY A TANDEM AZA-WITTIG ELECTROCYCLIC RING-CLOSURE OF N-VINYLIC PHOSPHAZENES

Citation
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
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
51
Issue
12
Year of publication
1995
Pages
3683 - 3690
Database
ISI
SICI code
0040-4020(1995)51:12<3683:ANAESO>2.0.ZU;2-Q
Abstract
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.