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Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones

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Abstract

A new one-pot reaction between polyfluoroalkylated 3-oxo esters, methyl ketones and primary or secondary alkyl amines is reported as an efficient approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones. The scope of three-component cyclization and its plausible mechanism are discussed. The described protocol makes it possible to vary the functional substituents in 2, 3 and 5 positions of carbocycles. Anhydrous conditions are necessary for the productive synthesis of aminocyclohexenones, whereas in the presence of water the competitive formation of alkyl ammonium salts of keto hydroxy carboxylates is observed. Dehydration of the aminocyclohexenones was effectively used for the synthesis of 3-alkylamino-5-trifluoromethylphenols, some of which exhibited moderate antifungal activities against eight pathogenic fungal strains.

Graphical abstract: Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones

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Publication details

The article was received on 05 Feb 2019, accepted on 25 Mar 2019 and first published on 26 Mar 2019


Article type: Paper
DOI: 10.1039/C9OB00293F
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones

    M. V. Goryaeva, S. O. Kushch, O. G. Khudina, Y. V. Burgart, Y. S. Kudyakova, M. A. Ezhikova, M. I. Kodess, P. A. Slepukhin, L. Sh. Sadretdinova, N. P. Evstigneeva, N. A. Gerasimova and V. I. Saloutin, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00293F

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