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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 11-12
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Original Articles

Michael-Type Addition Reactions of Some Enamines to Arylidenepyrazolones

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Pages 1987-1996 | Received 30 Jan 1989, Published online: 24 Oct 2006
 

Abstract

The reaction of the arylidenepyrazolones (1b-d) with l-morpholinocyclohexene (E2) in refluxing acetonitrile leads to the less substituted alkylated enamines 3b-d. On the other hand, the more substituted alkylated enamines 2a-d are formed when 1a-d react under the same conditions with l-piperidinocyclohexene (E1). The nature of the enamine is crucial. Nucleophilic attack of the enamine on the α, β-unsaturated carbonyl system of 1 gives rise to a zwitterionic intermediate which through α -proton loss leads to different Michael-type adducts depending on the enamine.

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