SYNTHESIS OF TETRAHYDRO-1-BENZAZOCIN-2(1H)-ONES USING 8-ENDO-TRIG RADICAL CYCLIZATION OF IS(PHENYLTHIO)-N-[O-(PROP-2-ENYL)PHENYL]ACETAMIDES

Authors
IKEDA M OBATA K OKA J ISHIBASHI H SATO T
Citation
M. Ikeda et al., SYNTHESIS OF TETRAHYDRO-1-BENZAZOCIN-2(1H)-ONES USING 8-ENDO-TRIG RADICAL CYCLIZATION OF IS(PHENYLTHIO)-N-[O-(PROP-2-ENYL)PHENYL]ACETAMIDES, Heterocycles, 44, 1997, pp. 203-212
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
44
Year of publication
1997
Pages
203 - 212
Database
ISI
SICI code
0385-5414(1997)44:<203:SOTU8R>2.0.ZU;2-Z
Abstract
The effects of N-substituents upon the 8-endo-trig radical cyclization of is(phenylthio)-N-[o-(prop-2-enyl)phenyl]acetamides (4) were examin ed. The N-(p-methoxybenzyl) (4a) and N-tosyl derivatives (4b), when tr eated with tributyltin hydride in the presence of a small amount of az oisobutyronitrile, gave regioselectively the corresponding ,6-tetrahyd ro-3-phenylthio-1-benzazocin-2(1H)-ones (5a,b) (8-endo cyclization pro ducts) in 40 and 47% yields, respectively, while the N-unsubstituted d erivative (4c) afforded the reduction products (6c) and (8) as the maj or products, Some chemical transformation reactions of 5a are also des cribed.