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Report | Regular issue | Vol 19, No. 4, 1982, pp.669-676
Published online, 1st January, 1970
DOI: 10.3987/R-1982-04-0669
Diazapolycyclic Compounds XXII. The Action of N-Chlorosuccinimide over Diazaquinone Adducts under Ionic and Free Radical Conditions

Fernando Gómez Contreras and Ana María Solana

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain


The action of N-chlorosuccinimide over 4a,12a-diazatetracyclic systems obtained by cycloaddition of benzo(g)phthalazine-1,4-dione with several dienes is reported. The reaction in acid aqueous medium leads to the formation of 1,2-chlorohydrins by ionic addition to the double bond at the terminal tetrahydropyridazine ring moiety. The stereochemical results of these additions are commented, and it can be deduced that the usual AdE2 mechanism is not followed. When the conditions favoring a free radical process are employed, the addition process is accompanied by substitution at the terminal aromatic ring.