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Paper | Regular issue | Vol 60, No. 1, 2003, pp.131-141
Published online, 25th November, 2002
DOI: 10.3987/COM-02-9642
Synthesis of Dibenzo[a,f]quinolizinium and 2-Phenyloxazolo[3,2-a]quinolinium Perchlorates via Acid-catalyzed Cyclization of 1-(2-Oxo-2-phenylethyl)quinoline-2(1H)-ones

I-Li Chen, Yeh-Long Chen, Tai-Chi Wang, and Cherng-Chyi Tzeng*

*School of Medicinal and Applied Chemistry, College of Life Science, Kaohsiung Medical University, 100 Shih Chuen 1st Rd., Kaohsiung 807, Taiwan, R.O.C.

Abstract

Treatment of certain N-alkylated quinolin-2(1H)-ones with concentrated H2SO4 afforded oxazolo[3,2-a]quinolin-10-ylium perchlorates via a Z-form enol intermediate while others gave dibenzo[a,f]quinolizinium perchlorates via an E-form enol intermediate. We examined the structure of starting N-alkylated quinolin-2(1H)-ones and found that a methoxy group substituted at R4 is required for the formation of tetracyclic dibenzo[a,f]quinolizinium perchlorates.