Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine, and indole via intramolecular Diels-Alder cycloadditions of neutral 2-azadienes

Francisco Palacios; Concepción Alonso; Patricia Amezua; Gloria Rubiales

doi:10.1021/jo016325v

Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine, and indole via intramolecular Diels-Alder cycloadditions of neutral 2-azadienes

J Org Chem. 2002 Mar 22;67(6):1941-6. doi: 10.1021/jo016325v.

Authors

Francisco Palacios¹, Concepción Alonso, Patricia Amezua, Gloria Rubiales

Affiliation

¹ Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco., Apartado 450, 01080 Vitoria, Spain. qoppagaf@ehu.vc.es

PMID: 11895415
DOI: 10.1021/jo016325v

Abstract

A method for the preparation of novel oxaza and diaza polycyclic 9-oxa-4-azaphenanthrene, 5H-pyrido[2,3-a]pyrrolizine, 5H,6H-pyrido[3,2-g]indolizine, and 5H,6H-indeno[2,1-a]indole is described, based on tandem reactions: aza-Wittig reaction of N-vinylic phosphazenes with functionalized aldehydes and an intramolecular aza-Diels-Alder reaction.