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

Triaryl-Substituted Divinyl Ketones Cyclization: Nazarov Reaction versus Friedel–Crafts Electrophilic Substitution Научная публикация

Журнал

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Вых. Данные

Год: 2016, Том: 18, Номер: 24, Страницы: 6260-6263 Страниц : 4 DOI: 10.1021/acs.orglett.6b03023

Авторы

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

Организации

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.

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.

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

Web of science:	WOS:000390180300012
Scopus:	2-s2.0-85006506892
OpenAlex:	W2559902807

БД	Цитирований
OpenAlex	20
Scopus	18
Web of science	18