Acetoacetamides add quantitatively to cyanogen in aprotic media at ambient conditions in the presence of [M(acac)2] (M = Cu or Ni; acac = acetylacetonate) complexes to give selectively 1:1 addition compounds. Products are amidic cyanoenaminones which can be converted thermally both in solution and in solid state into pyrrolinic cycloisomers. A variety of physicochemical methods including X-ray analysis, thermal analysis, 13C n.m.r. and 1H n.m.r. has been employed for characterizing the new compounds and monitoring the isomerization reactions.
Metal-catalysed highly selective synthesis of ?-amido-?-cyanoenaminones from acetoacetamides and cyanogen: physicochemical properties and solid-state conversion into pyrroline isomers
BASATO, MARINO;
1985
Abstract
Acetoacetamides add quantitatively to cyanogen in aprotic media at ambient conditions in the presence of [M(acac)2] (M = Cu or Ni; acac = acetylacetonate) complexes to give selectively 1:1 addition compounds. Products are amidic cyanoenaminones which can be converted thermally both in solution and in solid state into pyrrolinic cycloisomers. A variety of physicochemical methods including X-ray analysis, thermal analysis, 13C n.m.r. and 1H n.m.r. has been employed for characterizing the new compounds and monitoring the isomerization reactions.
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