Cleavage of the N(1)-C(4) bond of 4-(4 '-hydroxyphenyl)-azetidine-2-ones via quinone methide intermediates

Authors
Cabell, LA Hedrich, LW McMurray, JS
Citation
La. Cabell et al., Cleavage of the N(1)-C(4) bond of 4-(4 '-hydroxyphenyl)-azetidine-2-ones via quinone methide intermediates, TETRAHEDR L, 42(48), 2001, pp. 8409-8413
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
48
Year of publication
2001
Pages
8409 - 8413
Database
ISI
SICI code
0040-4039(20011126)42:48<8409:COTNBO>2.0.ZU;2-Q
Abstract
In this paper we describe a novel ring-opening reaction in which 4-(4'-hydr oxyphenyl)-azetidine-2-ones, on treatment with base, rearrange to quinone m ethide intermediates with concomitant cleavage of the C(4)-N(1) bond. The q uinone methide intermediate serves as a substrate for Michael-type 1,6 conj ugate additions. (C) 2001 Elsevier Science Ltd. All rights reserved.