REACTION OF 4-PHENYLBUT-3-EN-2-ONE WITH CYANOACETAMIDE IN 2-1 RATIO

The reaction of 4-phenylbut-3-en-2-one with cyanoacetamide is not conf ined 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-p henylbut-3-en-2-one with one of cyanoacetamide also takes place, the p roducts being hylene-8,9-diphenyl-3-azabicyclo[3.3.1]nonan-2-one and h enylbutyl)-4-phenyl-3,4-dihydropyridin-2(1H)-one. The latter compound cyclises in acid medium to form ethyl-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 .