ISSN:
0170-2041
Keywords:
Cinnamamides, α-acetyl
;
Malononitrile
;
4H-Pyrans
;
Michael additions
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction of α-acetylcinnamamides 7a-e with malononitrile using piperidine as the catalyst is described. When one or two equivalents of malononitrile are used, the 2-amino-4H-pyran 6a or the polyfunctionalized carbocycles 9b-e, respectively, can be isolated as major products, depending on the experimental conditions. Compounds 9b-e apparently arise from a sequential Michael plus Knoevenagel addition of two molecules of malononitrile followed by Thorpe cyclization. The structure of 9b was determined by an X-ray crystallographic analysis, which revealed a twisted cyclohexadiene ring with a characteristic crystal packing.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1993199301125
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