[3+3] Cyclization reactions of β-nitroenamines and β-enaminonitriles with α,β-unsaturated carboxylic acid chlorides |
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Authors: | Mihly V Pilipecz Tams R Varga Zoltn Mucsi Pl Scheiber Pter Nemes |
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Institution: | aDepartment of Chemistry, Faculty of Veterinary Science, Szent István University, H-1400 Budapest, PO Box 2, Hungary |
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Abstract: | New indolizidines, quinolizidines, and octahydro-pyrido1,2-a]azepines of lactam type were synthesized from 2-nitromethylene-pyrrolidine, -piperidine, and -hexahydroazepine, respectively, by 3+3] cyclizations with α,β-unsaturated carboxylic acid chlorides. In the case of quinolizidines, a double bond migration was observed, and explained in terms of amidity percentage. Cyanomethylene-pyrrolidine gave indolizidines of lactam type, while transformations of 1-cyanomethylene-tetrahydoisoquinoline resulted in lactams as well as ketones, when simple open-chain acid chlorides or cinnamoyl chloride were used, respectively. |
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