Reactions of β-dicarbonyl compounds with acyl cyanides catalyzed or promoted by metal centres in the homogeneous phase

Abstract

The C–C bond-forming reaction between β-dicarbonyl compounds and acyl cyanides is catalyzed by nickel acetylacetonate or promoted by tin tetrachloride. Thus, β-diketones react with acyl cyanides in the presence of catalytic amounts of [Ni(acac)2] to give β-enamino diketones 3. β-Enamino keto esters 8 or β-enamino diesters 9 are obtained in the reactions of methyl acetoacetate or methyl malonate with acyl cyanides in the presence of stoichiometric amounts of SnCl4. The reactions of acyl cyanides with methyl malonate also afford furanone derivatives 10, whose structure has been determined, in one case, by a single-crystal X-ray analysis. β-Keto amides react with acyl cyanides to give pyrrolidine derivatives 13 both under catalytic conditions and stoichiometric conditions where an equimolar equivalent of promoter was used.