Cyclization of Polarized Divinyl Ketones under Aqueous and Ambient Conditions

Cyclization of Polarized Divinyl Ketones under Aqueous and Ambient Conditions Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2020, Volume: 363, Number: 1, Pages: 251-258 Pages count : 8 DOI: 10.1002/adsc.202000956

Authors

Yadykov Anton V. ¹ , Yaminova Liana V. ¹ , Krayushkin Mikhail M. ¹ , Shirinian Valerii Z. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation.

An ‘on-water’ protocol has been developed for the synthesis of combretastatin A-4 (CA-4) analogues by cyclization of polarized triaryldivinyl ketones using hydrochloric acid as a promoter in 45–95% yields. The reaction time was reduced by about 30 times due to ultrasonic irradiation at ambient temperature. The other advantages of this new method are operational simplicity, easy workup, no column purification, and applicability on a gram-scale. It was shown that the amphiphilicity of the substrate and a low energy barrier of the reaction are a prerequisite for electrophilic and concerted reactions under aqueous and ambient conditions.

Yadykov A.V. , Yaminova L.V. , Krayushkin M.M. , Shirinian V.Z.
Cyclization of Polarized Divinyl Ketones under Aqueous and Ambient Conditions
Advanced Synthesis & Catalysis. 2020. V.363. N1. P.251-258. DOI: 10.1002/adsc.202000956 WOS Scopus OpenAlex

Web of science:	WOS:000588465400001
Scopus:	2-s2.0-85096966981
OpenAlex:	W3096084572

DB	Citing
OpenAlex	6
Scopus	6
Web of science	6