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Communication | Special issue | Vol 47, No. 2, 1998, pp.639-642
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)48
Tetracyclic Isoquinolones and Quinazolones via Aryl Radical Cyclizations

Bimal K. Banik, Vegesna S. Raju, Maghar S. Manhas, and Ajay K. Bose*

*Department of Chemistry and Chemical Biology, Stevens Institute of Technology, Castle Point on the Hudson, Hoboken, NJ 07030, U.S.A.

Abstract

The Schiff base from o-bromobenzaldehyde and allylamine was allowed to react with homophthalic anhydride to form an isoquinolone. Reaction of the same Schiff base with isatoic anhydride led to a quinazolone. Generation of a free radical from the bromoaryl moiety under the influence of tributyltin hydride converted the isoquinolone and the quinazolone to tetracyclic systems. This approach can lead to a convenient synthesis of alkaloids of the benzophenanthridine and protoberberine families.