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Paper | Special issue | Vol 44, No. 1, 1997, pp.203-212
Published online, 1st January, 1970
DOI: 10.3987/COM-96-S8
Synthesis of Tetrahydro-1-benzazocin-2(1H)-ones Using 8-endo-trig Radical Cyclization of 2,2-Bis(phenylthio)-N-[o-(prop-2-enyl)phenyl]acetamides

Masazumi Ikeda,* Ken-ichi Obata, Jun-ichiro Oka, Hiroyuki Ishibashi, and Tatsunori Sato

*Kyoto Pharmaceutical University, Misasagi-Shichonocho, Yamashina, Kyorto 607-8414, Japan


The effects of N-substituents upon the 8-endo-trig radical cyclization of 2,2-bis(phenylthio)-N-[o-(prop-2-enyl)phenyl]acetamides (4) were examined. The N-(p-methoxybenzyl) (4a) and N-tosyl derivatives (4b), when treated with tributyltin hydride in the presence of a small amount of azoisobutyronitrile, gave regioselectively the corresponding 3,4,5,6-tetrahydro-3-phenylthio-1-benzazocin-2(1H)-ones (5a,b) (8-endo cyclization products) in 40 and 47% yields, respectively, while the N-unsubstituted derivative (4c) afforded the reduction products (6c) and (8) as the major products. Some chemical transformation reactions of 5a are also described.