Issue 20, 1993

Reaction of 4-phenylbut-3-en-2-one with cyanoacetamide in 2 : 1 ratio

Abstract

The reaction of 4-phenylbut-3-en-2-one with cyanoacetamide is not confined to a 1 : 1 reaction [which results in formation of 3-cyano-6-methyl-4-phenylpyridin-2(1H)-one]. The reaction of 2 mole equivalents of 4-phenylbut-3-en-2-one with one of cyanoacetamide also takes place, the products being 1-cyano-6-hydroxy-6-methyl-4-methylene-8,9-diphenyl-3-azabicyclo[3.3.1]nonan-2-one and 3-cyano-6-methyl-3-(3-oxo-1-phenylbutyl)-4-phenyl-3,4-dihydropyridin-2(1H)-one. The latter compound cyclises in acid medium to form 6-acetyl-4-cyano-1-methyl-5,8-diphenyl-2-azabicyclo[2.2.2]octan-3-one. X-Ray crystal structures of the 3-azabicyclo[3.3.1]nonan-2-one and the 3-azabicyclo[2.2.2]octan-2-one derivatives are described.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 2479-2486

Reaction of 4-phenylbut-3-en-2-one with cyanoacetamide in 2 : 1 ratio

C. N. O'Callaghan, T. B. H. McMurry, C. J. Cardin and D. J. Wilcock, J. Chem. Soc., Perkin Trans. 1, 1993, 2479 DOI: 10.1039/P19930002479

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