Physical Sciences and Mathematics Commons^™

Synthesis Of Indolizines And Benzoindolizines By Annulation Of Donor-Acceptor Cyclopropanes With Electron-Deficient Pyridines And Quinolines, Nicholas A. Morra, Christian L. Morales, Barbora Bajtos, Xin Wang, Hyosook Jang, Jian Wang, Brian Pagenkopf

Chemistry Publications

The formal [3+2] dipolar cycloaddition (or annulation) of donor-acceptor cyclopropanoate esters with pyridines and 5-nitroquinoline is reported. Electron-deficient pyridine dipolarophiles (R=CN, CO₂Et, COMe) participate in the annulation whereas electron rich species do not. The product 2,3-dihydroindolizines undergo rapid autooxidation, and the X-ray structures for two of the aromatic products are reported.