UNCATALYZED CATIONIC OLEFIN CYCLIZATIONS OF N-VINYLIC ALPHA-CHLORO-ALPHA-THIOACETAMIDES - FORMATION OF BETA-LACTAMS AND GAMMA-LACTAMS

Authors
ISHIBASHI H NAKAHARU T NISHIMURA M NISHIKAWA A KAMEOKA C IKEDA M
Citation
H. Ishibashi et al., UNCATALYZED CATIONIC OLEFIN CYCLIZATIONS OF N-VINYLIC ALPHA-CHLORO-ALPHA-THIOACETAMIDES - FORMATION OF BETA-LACTAMS AND GAMMA-LACTAMS, Tetrahedron, 51(10), 1995, pp. 2929-2938
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
10
Year of publication
1995
Pages
2929 - 2938
Database
ISI
SICI code
0040-4020(1995)51:10<2929:UCOCON>2.0.ZU;2-J
Abstract
N-Vinylic alpha-chloro-alpha-thioacetamides were found to cyclize with out a catalyst in two different manners depending upon the nature of t he substituents at the terminus of the N-vinylic bond. Thus, bis(pheny lthio)-substituted enamides 8a-c cyclized in a 4-exo-trig manner to gi ve 4-methylene-beta-lactams 10a-c, whereas mono(phenylthio)-, monophen yl-, diphenyl-, and dialkyl-substituted congeners 23a,b, 28, and 38 cy clized in a 5-endo-trig manner to give gamma-lactams 26a,b, 30, and 39 , respectively. The product 38 was transformed into an anticonvulsant agent ethosuximide (42).