Functionalized chloroenamines in aminocyclopropane synthesis - V. synthesis and reactions of aminocyclopropylketones |
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Authors: | Elmar Vilsmaier, Ralph Drrenb cher,Lutz Muller |
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Affiliation: | Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schroedinger-StraBe, D-6750 Kaiserslautern, Germany. |
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Abstract: | Conjugated acylated chloroenamines 5A,C were available by chlorination of mixtures of acylated enamines 8A,C/9A,C by NCS at 0°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-cyclopropyiketones 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. |
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