COMMUNICATIONS
DOI: 10.1002/adsc.202001474
Visible Light-Promoted Selenylation/Cyclization of Enaminones
toward the Formation of 3-Selanyl-4H-Chromen-4-Ones
a
a
b
a,
Hao-Yang Liu, Jia-Rong Zhang, Guo-Bao Huang, Yi-Huan Zhou, *
a,
a, b,
Yan-Yan Chen, * and Yan-Li Xu *
a
Pharmacy School of Guilin Medical University
Guilin, 541004 People’s Republic of China
E-mail: zyh8312020@163.com; chenyy269614@163.com; yanli.xu@163.com
Key Laboratory of Agricultural Resources Chemistry and Biotechnology
b
College of Chemistry and Food Science of Yulin
Normal University
Yulin 537000, People’s Republic of China
Manuscript received: November 26, 2020; Revised manuscript received: January 19, 2021;
Version of record online: Februar 4, 2021
chromones containing selenyl-substituents show
Abstract: A simple and efficient visible-light-pro-
unique bioactivities and chemical properties, and
moted selenylation/cyclization of enaminones have
widely adopted in drug design and regulation of
been realized for the practical synthesis of 3-
[6]
biological processes.
selanyl-4H-chromen-4-ones. This reaction is per-
formed in the mild conditions, no transition metal
catalyst or photocatalysts and no additional oxidants
are required. In addition, the 3-selanyl-4H-chromen-
As 3-selenochromones are an important class of
compounds, much efforts has been devoted to the
[7]
assembly of this compound. Among them, the
reactions based on the featured chromone annulation
of easily available 2-hydroxyphenyl enaminones have
been proved to be the most reliable and broadly
4
-ones could be easily converted to selanyl-func-
tionalized pyrimidines by reacting with benzamidine
substrates.
[8]
applicable one. For example, Zhou’s group reported a
metal-free approach to 3-selenocyanochromone via α-
CÀ H selenocyanation of enaminones using PhI(OAc)
2
Keywords: 2-hydroxyphenyl enaminones; selenyla-
tion; 3-selanyl-4H-chromen-4-ones; selanyl-function-
alized pyrimidines; visible-light-promoted
as an oxidant in an aqueous medium (Scheme 1a).
[9]
[10]
Wan’s group and Braga’s group
reported KIO3-
catalyzed synthesis of 3-selenochromones from 2-
hydroxyphenyl enaminones and diorganyl diselenides,
in which using ethyl lactate and glycerol as solvent,
[11]
Chromone moiety is a well-documented privileged respectively (Scheme 1b). Blond’s group have devel-
structure in the natural products and pharmaceuticals oped AgOTf-mediated synthesis of 3-selenochromones
[1]
for discovering lead compounds and medicines. In through the reaction of 2-hydroxy-phenyl enaminones
particular, C3-substituted chromones are recently and phenylselenyl chloride (Scheme 1c). Although
drawing considerable attention as they exhibit a variety diverse approaches toward the synthesis of 3-seleno-
[2]
of physiological and biological activities. Several
[3]
representative compounds with anti-cancer, anti-
oxidant, and anti-inflammatory activities, are shown in
Figure 1.
Organoselenium compounds have attracted consid-
erable attention in medicinal chemistry owing to their
[4]
well-known biological activities, which mainly attrib-
uted to the fact that the selenium atom may serve as an
electron donor or a hydrogen bond acceptor in these
applications, altering the chemical characteristics of
Figure 1. Biologically Active Molecules including C3-Substi-
tuted Chromones Moiety.
[5]
enzyme active sites. Recent studies revealed that
Adv. Synth. Catal. 2021, 363, 1656–1661
1656
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