The reaction of the pyrrolidine enamine of cyclohexanone with several malonic acid derivatives gave good yields of the corresponding Knoevenagel adducts when one of the activating substituents was a cyano group. The above enamine, after alkylation at the 2-position with methyl acrylate, gave similar yields of Knoevenagel products. Reaction of the alkylated enamine with lithioacetonitrile gave, after acidification, an annulated product by internal Knoevenagel reaction. The latter product was also obtained by a Dieckmann ring closure reaction. The Michael reaction of the substituted Knoevenagel products was examined and found to be facile with several nucleophiles. However, no ring closure products resulting from further reaction of the intermediate dicyanomethine anions were detected.Ball State UniversityMuncie, IN 47306
| Identifer | oai:union.ndltd.org:BSU/oai:cardinalscholar.bsu.edu:handle/183099 |
| Date | 03 June 2011 |
| Creators | Troxel, Richard L. |
| Contributors | Kruger, Terry L. |
| Source Sets | Ball State University |
| Detected Language | English |
| Format | iii, 94 leaves : ill. ; 28 cm. |
| Source | Virtual Press |
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