title: Triaryl-Substituted Divinyl Ketones Cyclization: Nazarov Reaction versus Friedel-Crafts Electrophilic Substitution.
abstract: The acid-catalyzed cyclization of a wide range of triaryl-substituted divinyl ketones has been studied. It was found that the reaction pathway strongly depends on the nature of the aryl substituent at the α-position to the carbonyl group. An electron-rich aromatic substituent promotes the reaction to proceed through the intramolecular Friedel-Crafts electrophilic substitution giving dihydronaphthalene derivatives. In contrast, the presence of an electron-deficient substituent is favorable for the Nazarov 4π-conrotatory cyclization yielding triaryl-substituted cyclopentenones. The electrophilic substitution reaction was applied to thiophene and thiazole derivatives.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, RAS , Moscow 119991, Russia.
authors.forename: Valerii Z
authors.identifier: 0000-0001-9480-3565
authors.initials: VZ
authors.lastname: Shirinian
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, RAS , Moscow 119991, Russia.
authors.forename: Andrey G
authors.initials: AG
authors.lastname: Lvov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, RAS , Moscow 119991, Russia.|Higher Chemical Colleges, D.I. Mendeleev University of Chemical Technology of Russia , Moscow 125047, Russia.
authors.forename: Anton V
authors.initials: AV
authors.lastname: Yadykov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, RAS , Moscow 119991, Russia.|D.I. Mendeleev University of Chemical Technology of Russia , Moscow 125047, Russia.
authors.forename: Liana V
authors.initials: LV
authors.lastname: Yaminova
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, RAS , Moscow 119991, Russia.
authors.forename: Vadim V
authors.initials: VV
authors.lastname: Kachala
authors.affiliation: Scientific Technological Center of Organic and Pharmaceutical Chemistry, NAS RA , Yerevan 0014, Republic of Armenia.
authors.forename: Ashot I
authors.initials: AI
authors.lastname: Markosyan