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Synlett 1991; 1991(11): 816-818
DOI: 10.1055/s-1991-20888
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N-Phenyl-2-cyano-1-azadienes: New Versatile Heterodienes in the Diels-Alder Reaction

Nicholas J. Sisti* , Frank W. Fowler, David S. Grierson
  • *Institut de Chimie des Substances Naturelles, F-91198 Gif-sur-Yvette, France
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Publication Date:
07 March 2002 (online)

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N-Phenyl-2-cyano-1-aza-1,3-butadiene (6), prepared from aniline and acryloyl chloride in 3 steps, was shown to undergo efficient Diels-Alder cycloaddition with both electron rich and electron poor dienophiles giving 1,2,3,4-tetrahydropyridine derivatives 12 to 17. The intramolecular reaction of azadiene 10 (N-(2-allylphenyl)-2-cyano-1-aza-1,3-butadiene) provides ready access to dihydroindole 11 (6-cyano-8,9,9a,10-tetrahydropyrido[1,2-a]indole).