Premium
Synthesis of Indolizines and Benzoindolizines by Annulation of Donor‐Acceptor Cyclopropanes with Electron‐Deficient Pyridines and Quinolines
Author(s) -
Morra Nicholas A.,
Morales Christian L.,
Bajtos Barbora,
Wang Xin,
Jang Hyosook,
Wang Jian,
Yu Ming,
Pagenkopf Brian L.
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600298
Subject(s) - annulation , chemistry , pyridine , autoxidation , electron acceptor , cycloaddition , medicinal chemistry , electron , electron donor , photochemistry , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
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.