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Triaryl-Substituted Divinyl Ketones Cyclization: Nazarov Reaction versus Friedel–Crafts Electrophilic Substitution Full article

Journal Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052
Output data Year: 2016, Volume: 18, Number: 24, Pages: 6260-6263 Pages count : 4 DOI: 10.1021/acs.orglett.6b03023
Authors Shirinian Valerii Z. 1 , Lvov Andrey G. 1 , Yadykov Anton V. 2,1 , Yaminova Liana V. 1,3 , Kachala Vadim V. 1 , Markosyan Ashot I. 4
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, RAS , Moscow 119991, Russia.
2 Higher Chemical Colleges, D.I. Mendeleev University of Chemical Technology of Russia, Moscow 125047, Russia
3 D.I. Mendeleev University of Chemical Technology of Russia, Moscow 125047, Russia
4 Scientific Technological Center of Organic and Pharmaceutical Chemistry, NAS RA , Yerevan 0014, Republic of Armenia.

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.
Cite: Shirinian V.Z. , Lvov A.G. , Yadykov A.V. , Yaminova L.V. , Kachala V.V. , Markosyan A.I.
Triaryl-Substituted Divinyl Ketones Cyclization: Nazarov Reaction versus Friedel–Crafts Electrophilic Substitution
Organic Letters. 2016. V.18. N24. P.6260-6263. DOI: 10.1021/acs.orglett.6b03023 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000390180300012
Scopus: 2-s2.0-85006506892
OpenAlex: W2559902807
Citing:
DB Citing
OpenAlex 20
Scopus 18
Web of science 18
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