Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 266, Issue -, Pages -Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2023.110088
Keywords
Ethyl 4; 4-difluoroacetoacetate; Formaldehyde; Primary amines; Amino acid esters; Multicomponent reactions; 1; 2; 3; 4-tetrahydropyridines
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Difluoromethyl-containing diethyl 1,2,3,4-tetrahydropyridine-3,5-dicarboxylate derivatives were synthesized in up to 90% yields by the Mannich reaction of ethyl 4,4-difluoroacetoacetate with formaldehyde and primary amine hydrochlorides. The effects of the reactant structure and reaction conditionson the efficiency of formation of 1,2,3,4-tetrahydropyridines and hexahydropyrimidines was studied.
Difluoromethyl-containing diethyl 1,2,3,4-tetrahydropyridine-3,5-dicarboxylate derivatives were synthesized in up to 90% yields by the Mannich reaction of ethyl 4,4-difluoroacetoacetate with formaldehyde and primary amine hydrochlorides. The effects of the reactant structure and reaction conditionson the efficiency of formation of 1,2,3,4-tetrahydropyridines and hexahydropyrimidines was studied. In the presence of NaCl in an acetate buffer (pH 4), the 1,2,3,4-tetrahydropyridine structure is formed selectively. When 4-aminophenol hydrochloride is used, the 3,4,5,6-tetrahydropyrimidin-1-ium difluoroacetate salt is produced, apart from the target product. The reactions with (S)-alpha-amino acid ester hydrochlorides afford mixtures of two diastereomeric 1,2,3,4-tetrahydropyridines.
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