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Communication | Special issue | Vol 37, No. 3, 1994, pp.1455-1458
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S126
A Study of the Hetero Diels-Alder Reaction of N-Alkyl-2-cyano-1-azadienes with 2-Vinylindole

Bouchra Dufour, Irina Motorina, Frank W. Fowler,* and David S. Grierson*

*Institut des Chimie des Substances Naturelles, C.N.R.S., Avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France

Abstract

The N-alkyl-2-cyano-1-azadienes (2a) and (2b) derived from ethanolamine react with 2-vinylindole under thermal conditions to give the Michael addition adducts (9) and (9’) as the principle product. In the reaction of 2a with vinylindole the Diels-Alder product (11) was also isolated. In the reaction with 2b, formation of compounds (9) was accompanied by the cyclized product (10) and the Diels-Alder adduct (13).