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Cyclization of Polarized Divinyl Ketones under Aqueous and Ambient Conditions
Author(s) -
Yadykov Anton V.,
Yaminova Liana V.,
Krayushkin Mikhail M.,
Shirinian Valerii Z.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000956
Subject(s) - chemistry , aqueous solution , electrophile , substrate (aquarium) , hydrochloric acid , combinatorial chemistry , organic chemistry , catalysis , oceanography , geology
Abstract 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.