SIMPLE AND CONDENSED BETA-LACTAMS .29. SYNTHESIS AND BASE-CATALYZED RING TRANSFORMATION OF THOXYPHENYL)-4-OXOAZETIDIN-2-YL)]THIAZOL-2(3H)-ONE

Authors
SAPI A FETTER J LEMPERT K KAJTARPEREDY M CZIRA G
Citation
A. Sapi et al., SIMPLE AND CONDENSED BETA-LACTAMS .29. SYNTHESIS AND BASE-CATALYZED RING TRANSFORMATION OF THOXYPHENYL)-4-OXOAZETIDIN-2-YL)]THIAZOL-2(3H)-ONE, Tetrahedron, 53(37), 1997, pp. 12729-12738
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
37
Year of publication
1997
Pages
12729 - 12738
Database
ISI
SICI code
0040-4020(1997)53:37<12729:SACB.S>2.0.ZU;2-F
Abstract
4-[(2RS,3RS)-3-Hydroxy- (1b) and thoxyphenyl)-4-oxo-azetidin-2-yl]thia zol-2(3H)-one (16b) were synthesised. While the former was smoothly re arranged into )-1,5-dihydrothiazolo[3,4-a]pyrazine-3,6(7H)-dione (7b) on treatment with Na2CO3 under mild conditions, the latter was found t o be stable to Na2CO3 under the same conditions. The structural prereq uisites for type 1 --> 7 ring transformations, including cleavage of t he 3-4 bond (azetidin-2-one numbering) of the beta-lactam ring are def ined. (C) 1997 Elsevier Science Ltd.