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

✍ Scribed by Nicholas A. Morra; Christian L. Morales; Barbora Bajtos; Xin Wang; Hyosook Jang; Jian Wang; Ming Yu; Brian L. Pagenkopf

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
165 KB
Volume
348
Category
Article
ISSN
1615-4150

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✦ Synopsis

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, CO~2~Et, 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.

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