The mechanism of the hantzsch pyridine synthesis: A study by 15N and 13C NMR spectroscopy
1986; Elsevier BV; Volume: 42; Issue: 20 Linguagem: Inglês
10.1016/s0040-4020(01)88178-3
ISSN1464-5416
AutoresAlan R. Katritzky, Daryl L. Ostercamp, Taher I. Yousaf,
Tópico(s)Synthesis and biological activity
ResumoThe mechanism of the reactions of ammonia and benzaldehyde with three different beta-dicarbonyl compounds to form the corresponding dihyropyridines has been followed by NMR. In each case the pathway is shown to involve the reaction of benzaldehyde with one molecule of beta-dicarbonyl to give chalcone, and of the ammonia with a second molecule of beta-dicarbonyl to give an enamine. The rate determining stage is shown to be the Michael addition of the chalcone to the enamine.
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