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. Issue 17 (2nd April 2019)

• Record Type: Journal Article
• Authors: Goryaeva, Marina V.; Kushch, Svetlana O.; Khudina, Olga G.; Burgart, Yanina V.; Kudyakova, Yulia S.; Ezhikova, Marina A.; Kodess, Mikhail I.; Slepukhin, Pavel A.; Sadretdinova, Lilya Sh.; Evstigneeva, Natalya P.; Gerasimova, Natalya A.; Saloutin, Victor I.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 17(2019)
• Page Start: 4273
• Page End: 4280
• Publication Date: 2019-04-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00293f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A new route to aminocyclohexenones is reported. 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.