Synthesis of Indolizines and Benzoindolizines by Annulation of Donor-Acceptor Cyclopropanes with Electron-Deficient Pyridines and Quinolines

Authors

Nicholas A. Morra
Christian L. Morales
Barbora Bajtos
Xin Wang
Hyosook Jang
Jian Wang
Brian Pagenkopf, University of Western OntarioFollow

Document Type

Article

Publication Date

11-27-2006

Journal

Advanced Synthesis and Catalysis

Volume

348

Issue

16-17

First Page

2385

Last Page

2390

URL with Digital Object Identifier

10.1002/adsc.20060029

Abstract

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.