Ring transformations of 2,3-dihydroisoxazoles via azomethine ylides - Formation of annulated 5-and 7-membered N-heterocycles

Authors
Friebolin, W Eberbach, W
Citation
W. Friebolin et W. Eberbach, Ring transformations of 2,3-dihydroisoxazoles via azomethine ylides - Formation of annulated 5-and 7-membered N-heterocycles, TETRAHEDRON, 57(20), 2001, pp. 4349-4358
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
20
Year of publication
2001
Pages
4349 - 4358
Database
ISI
SICI code
0040-4020(20010514)57:20<4349:RTO2VA>2.0.ZU;2-2
Abstract
On thermal activation the 2,3-dihydroisoxazoles 12-14 are transformed into annulated dihydroazepines 15-17 as main products, besides minor amounts of the corresponding pyrrole derivatives 18-20. In the proposed mechanism the azomethine ylides of type III and VI are involved as intermediates which un dergo 1,5- and 1,7-ring closure reactions, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.