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

Jun-An Xiao; Xiu-Liang Cheng; Ru-Fang Meng; Xiao-Shi Qin; Hai Peng; Ji-Wei Ren; Zhen-Zhen Xie; Jian-Guo Cui; Yan-Min Huang

doi:10.1055/s-0040-1707315

Synthesis, Table of Contents

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∗

^aGuangxi 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

^aGuangxi 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

^aGuangxi 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

^aGuangxi 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

^aGuangxi 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∗

^bInstitute of Drug Discovery Technology, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China Email: renjiwei@nbu.edu.cn

,

Zhen-Zhen Xie

^cCollege of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China

,

Jian-Guo Cui

^aGuangxi 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∗

^aGuangxi 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

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Abstract

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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.

Key words

selenocyanation - chromones - grinding - organoselenium compounds - solvent-free conditions

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References

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