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Paper | Regular issue | Vol 31, No. 12, 1990, pp.2131-2138
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5513
Synthesis of Isoquino[1,2-b]quinazolines by Cycloaddition Reaction

Isabelle Kanmacher, Jean-Francois Stambach,* and Louis Jung

*Laboratoire de Chimie Thérapeutique, U.F.R. des Sciences Pharmaceutiques, Université Louis Pasteur, 74, route du Rhin, BP 24, 67401 ILLKIRCH Cedex, France

Abstract

The cycloaddition reaction of 3,4-dihydroisoquinolinium salts (2c,d) with 2-aminobenzaldehydes (1a,b) was a convenient way to obtain 5,6,13,13a-tetrahydro-8H-isoquinol[1,2-b]quinazolium salts (3a-d). The reduction, transposition and oxidation of these compounds gave 8H-isoquino[1,2-b]quinazoline derivatives in good yields. The mechanism of the cycloaddition reaction is discussed. The cis and trans isomer of the tetrahydro derivative (5d) have been isolated and identified by an infrared spectroscopic study.