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Paper | Regular issue | Vol 48, No. 9, 1998, pp.1867-1878
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8220
Diels-Alder Cycloaddition of Methacrolein N,N-Dimethylhydrazone to 1,4-Naphthoquinone Derivatives

Alma M. Jiménez, M. Victoria Martín, and M. Carmen Paredes*

*Instituto de Química Médica, C. S. I. C., Calle Juan de Cierva, 3, E-28006 Madrid, Spain

Abstract

Diels-Alder cycloadditions of naphthoquinone derivatives (3-8) with methacrolein N,N-dimethylhydrazone (9) have been investigated. In the reaction with the quinones (3-4) and (8) the initial cycloadducts (10, 11 and 17a,b) were isolated in good yields. However, the cycloaddition with quinones (5-7) affords directly the corresponding aromatized azaanthraquinones (12, 15a and 16a,b) in good yields.