FUNCTIONALIZED CHLOROENAMINES IN AMINOCYCLOPROPANE SYNTHESIS - V. SYNTHESIS AND REACTIONS OF AMINOCYCLOPROPYLKETONES

Article abstract of DOI:10.1016/S0040-4020(01)81467-8

Conjugated acylated chloroenamines 5A,C were available by chlorination of mixtures of acylated enamines 8A,C/9A,C by NCS at 0 deg C.Nonconjugated chloroenamines 10Aa and 10Ba could be obtained by NCS-chlorination of the conjugated acylenamines 9A,B at low temperature.Reaction of 5Aa-5Ac, 5Ae, 5Af with cyanide produced morpholinocyclopropylketones 11A.In two cases aminofurans 12Ad and 12Ca resulted as products of this reaction.More generally amino-aryl-furans 12 were formed by thermolysis of the aryl-cyclopropylketones 11.Amino-alkyl-furans as 12Ae and 12Af only could be trapped by a Diels-Alder reaction leading to 16Ae and 16Af.Epoxyenamines 29A,B unexpectedly were produced from the interaction of cyanide with the chloroenamines 10Aa and 10Ba.