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Communication | Regular issue | Vol 29, No. 1, 1989, pp.11-20
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4763
Regioselectivity in the Diels-Alder Reactions of 2-Vinylindoles and Pyrano[3,4-b]indol-3-ones with CC-Dienophiles

Ulf Pindur,* Manfred Eitel, and Erfanian Abdoust-Houshang

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

Abstract

Diels-Alder reactions of 2-vinylindoles 1 and methylated pyrano[5,4-b]indol-3-ones 6 with acceptor-substituted CC-dienophiles (e.g.propynoates, ethyl phenylpropynoate, acrylonitrile, α-chlnroacrylonitrile, methyl acrylate, 1-penten-3-one) proceed with poor to high regioselectivities to furnish functionalized carbazole derivatives. MNDO calculations have been carried out for the 2-vinylindole and pyrano[3,4-b] indol-3-one parent compounds and, in most cases, qualitative FMO analyses correctly predict the major products. The regiochemistries of the products from the reactions of the pyrano[3,4-b]indol-3-ones 6 with ethyl phenylpropynoate can be predicted by the simple charge controlled orientation in the transition states.