The knoevenagel reaction of malononitrile with some cyclic β-keto-esters—II
1974; Elsevier BV; Volume: 30; Issue: 15 Linguagem: Inglês
10.1016/s0040-4020(01)97115-7
ISSN1464-5416
AutoresJ. L. VAN DER BAAN, F. Matthias Bickelhaupt,
Tópico(s)Phosphorus compounds and reactions
ResumoThe formation of alkoxypyridinols 3a and 3b from the Knoevenagel reaction products 2a and 2b was shown to proceed by a mechanism in which the ester CO group initiates ring closure by intramolecular nucleophilic attack on the cyano group, possibly assisted by an acidic catalyst. Opening of the oxygen ring after nucleophilic attack by a basic catalyst on the former ester carbonyl C atom results in the formation of an amide, which in turn affords the alkoxypyridinols by a conventional cyclization mechanism.
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