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Synthesis of Multifunctionalized 2,3-Dihydro-4-pyridones and 4-Pyridones via the Reaction of Carbamoylated Enaminones with Aldehydes

Author:
Obydennov, Dmitrii L., El-Tantawy, Asmaa I., Sosnovskikh, Vyacheslav Y.
Source:
Journal of organic chemistry 2018 v.83 no.22 pp. 13776-13786
ISSN:
1520-6904
Subject:
aldehydes, aromatization, chemical structure, crystallization, diastereoselective synthesis, iodine, organic chemistry, tautomerization
Abstract:
The novel and effective diastereoselective synthesis of multifunctionalized dihydropyridones, including CF₃-substituted derivatives, has been developed on the basis of the piperidine-promoted domino reaction of carbamoylated enaminones with aldehydes. The products have been prepared in 38–90% yields and can be easily isolated by crystallization. Tautomerism, epimerization, and atropisomerism of dihydropyridones have been studied. The use of the resulting dihydropyridones in the synthesis of 1,2,6-trisubstituted 4-pyridone-3-carboxamides has been demonstrated via oxidative aromatization initiated by iodine.
Agid:
6212485