Oxidative [4+2] Annulation of Pyrrole-2-carbaldehyde Derivatives with o-Hydroxyphenyl Propargylamines: Syntheses of 5,6,7-Trisubstituted Indolizines

Chemistry. 2024 Nov 12;30(63):e202402487. doi: 10.1002/chem.202402487. Epub 2024 Oct 16.

Abstract

A base promoted oxidative [4+2] annulation of pyrrole-2-carbaldehyde derivatives with o-hydroxyphenyl propargylamines for the synthesis of highly substituted indolizines has been developed. Using DBN as base, a broad range of 5,6,7-trisubstituted indolizines have been prepared in good to excellent yields under mild conditions, and many useful functional groups can be tolerated.

Keywords: 1,6-addition; 5,6,7-trisubstituted indolizine; [4+2] annulation; o-hydroxyphenyl propargylamines; ortho-alkynyl quinone methide.