Synthesis 2021; 53(05): 954-960
DOI: 10.1055/s-0040-1707315
paper

Straightforward Synthesis of 3-Selenocyanato-Substituted Chromones through Electrophilic Selenocyanation of Enaminones under Grinding Conditions

Jun-An Xiao
a  Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. of China   Email: jaxiao@csu.edu.cn   Email: huangyanmin828@163.com
,
Xiu-Liang Cheng
a  Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. of China   Email: jaxiao@csu.edu.cn   Email: huangyanmin828@163.com
,
Ru-Fang Meng
a  Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. of China   Email: jaxiao@csu.edu.cn   Email: huangyanmin828@163.com
,
Xiao-Shi Qin
a  Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. of China   Email: jaxiao@csu.edu.cn   Email: huangyanmin828@163.com
,
Hai Peng
a  Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. of China   Email: jaxiao@csu.edu.cn   Email: huangyanmin828@163.com
,
Ji-Wei Ren
b  Institute of Drug Discovery Technology, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China   Email: renjiwei@nbu.edu.cn
,
Zhen-Zhen Xie
c  College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China
,
Jian-Guo Cui
a  Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. of China   Email: jaxiao@csu.edu.cn   Email: huangyanmin828@163.com
,
Yan-Min Huang
a  Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. of China   Email: jaxiao@csu.edu.cn   Email: huangyanmin828@163.com
› Author Affiliations
We are grateful to the National Natural Science Foundation of China (21861008), the Department of Science and Technology of Guangxi (AD19245049), the Natural Science Foundation of Guangxi (2018GXNSFBA138037, 2018GXNSFAA281245), and the ‘BAGUI Scholar’ program of Guangxi Province of China for generous financial support.


Abstract

A metal- and oxidant-free method for preparing 3-selenocyanato-substituted chromones from 2-hydroxyphenyl enaminones by using a newly developed electrophilic selenocyanating reagent is reported­. A series of 3-selenocyanato- or 3-thiocyanato-substituted chromones, as well as 3-selenocyanato- or 3-thiocyanato-substituted quinolinones was obtained in good to excellent yields under grinding reaction conditions. The generality and utility of this approach were demonstrated by a scale-up reaction and transformations of one of the products.

Supporting Information



Publication History

Received: 06 August 2020

Accepted after revision: 07 September 2020

Publication Date:
12 October 2020 (online)

© 2020. Thieme. All rights reserved

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