Regioselective intramolecular cyclization of o -alkynyl arylamines with the in situ formation of ArXCl to construct poly-functionalized 3-selenylindoles

In this article, a practical and metal-free method for the synthesis of poly-functionalized 3-selenyl/sulfenyl/telluriumindoles from -alkynyl arylamines has been achieved. In this protocol, the formation of selenenyl chloride, sulfenyl chloride or tellurenyl chloride is considered as the key interme...

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Published inRSC advances Vol. 13; no. 9; pp. 6210 - 6216
Main Authors Yu, Minhui, Jin, Tao, Wang, Xiaohua, Li, Haohu, Ji, Decai, Yao, Jinzhong, Zeng, Heyang, Shi, Senlei, Xu, Kaimeng, Zhang, Lianpeng
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 14.02.2023
The Royal Society of Chemistry
Subjects
Amines
Chemistry
Chlorides
Organic compounds
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Summary:In this article, a practical and metal-free method for the synthesis of poly-functionalized 3-selenyl/sulfenyl/telluriumindoles from -alkynyl arylamines has been achieved. In this protocol, the formation of selenenyl chloride, sulfenyl chloride or tellurenyl chloride is considered as the key intermediate and the 3-selenyl/sulfenyl/telluriumindoles can be obtained in good to excellent yields. Furthermore, the product 2-phenyl-3-(phenylselanyl)-1-tosyl-1 -indole can be selectively oxidized to compounds 2-phenyl-3-(phenylseleninyl)-1-tosyl-1 -indole and 2-phenyl-3-(phenylselenonyl)-1-tosyl-1 -indole in good yields.
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Equal contributions to this manuscript.
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra00030c