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Note | Special issue | Vol 66, No. 1, 2005, pp.659-666
Published online, 28th October, 2005
DOI: 10.3987/COM-05-S(K)64
Synthesis of N-Methylphenanthridinone Derivatives Fused with a Silacyclohexane Ring by Radical Reaction Using Tributyltin Hydride

Yuya Hoshino and Osamu Hoshino*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

Radical reaction of (N-methyl-7-bromo-2,2-dimethyl-2-silatetralin-6-ylamino)veratramide (8a) and -piperonamides (8b) in boiling benzene using tributyltin hydride and AIBN gave two kinds of N-methylphenanthridinone derivatives (15 and 16), which were cyclized at 6- and 2-positions of aroylic acid moiety. On the other hand, similar reaction of N-methyl-N-(2-bromoveratryl and 2-bromopiperonyl)-2,2-dimethyl-2-silatetralin-6-carboxamides (14) produced N-methylphenanthridinone deivatives (17) as each sole product, in which cyclization occurred at 5-position of 2-silatetralin moiety.