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Paper | Regular issue | Vol 29, No. 9, 1989, pp.1709-1719
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5020
New Reactivity of Stable Indole-2,3-quinodimethane Equivalents: [4+2]Cycloaddition, Cycloreversion, Sigmatropic Rearrangement, and Elimination Processes in the Reactions of 1,4-Dimethylpyrano[3,4-b]indole-3-one and 1-Methylpyrido[3,4-b]indol-3-one with CC-Dienophiles

Houshang Erfanian-Abdoust and Ulf Pindur*

*Department of Chemistry and Pharmacy, Institute of Pharmacy, University of Mainz, Saarstrasse 21, D-55122 Mainz, Germany

Abstract

The reactions of 1,4-dimethylpyrano[3,4-b]indol-3-one (1a) with tetracyanoethylene and N-phenylmaleimide give the variously functionalized carbazole derivatives 3-7 and 9-12 via [4+2] cycloaddition, [4+2] cycloreversion, and some sigmatropic rearrangements. The Diels-Alder reactions of 1-methylpyrido [3,4-b] indol-3-one (1b) with several CC-dienophiles also give rise to the interesting carbazoles 14-18. In the latter case, the primarily formed cycloadducts can be isolated and, in reactions of 1b with unsymmetrical dienophiles, the products are formed in high regioselectivities.