6533b7d8fe1ef96bd126a427

RESEARCH PRODUCT

New Strategies for the Synthesis of Fluorinated Vinylogous Amidines and β-Enamino Ketones

Antonio Simon FuentesBelén PinaSantos FusteroGarcía De La Torre M

subject

chemistry.chemical_classificationAmidineHydrolysischemistry.chemical_compoundKetonechemistryOrganic ChemistryRegioselectivityOrganic chemistryBeta (finance)Tautomer

description

Reaction of fluorinated imidoyl chlorides 3 with ketimines 1a provides fluorinated 1,3-diimines, which were exclusively isolated as vinylogous amidine tautomers 2beta, with good yields. Fluorinated beta-enamino ketones 4 are obtained by regioselective hydrolysis of 2. Complementary methods for the synthesis of regioisomeric beta-enamino ketones 4 and 5 are also reported. These methods include the reaction of azaenolates of ketimines with fluorinated esters 6 and reactions of ketone enolates with fluorinated imidoyl chlorides 3. The behavior of these systems in hydrolysis reactions was also tested.

yearjournalcountryeditionlanguage
2001-10-25The Journal of Organic Chemistry
https://doi.org/10.1021/jo990392w