Metal-catalysed highly selective synthesis of α-amido-β-cyanoenaminones from acetoacetamides and cyanogen: physicochemical properties and solid-state conversion into pyrroline isomers
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 12,p. 2019-2025
- https://doi.org/10.1039/p29850002019
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.Keywords
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