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Iodobenzene Dichloride/Zinc Chloride‐Mediated Synthesis of N ‐Alkoxyindole‐3‐carbonitriles from 3‐Alkoxyimino‐2‐arylalkylnitriles via Intramolecular Heterocyclization
Author(s) -
Yun Zhongxiang,
Cheng Ran,
Sun Jiyun,
ZhangNegrerie Daisy,
Du Yunfei
Publication year - 2018
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.201701111
Subject(s) - chemistry , iodobenzene , hypervalent molecule , intramolecular force , reagent , zinc , chloride , iodide , iodine , lewis acids and bases , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis
A series of N ‐alkoxyindole‐3‐carbonitriles were synthesized, under mild conditions, via intramolecular heterocyclization of the readily available 3‐alkoxyimino‐2‐arylalkylnitriles mediated by iodobenzene dichloride/zinc chloride. The mechanism of the reaction proposes the formation of a key intermediate of nitrenium cation from a chlorination and dechlorination process facilitated by the hypervalent iodine reagent and Lewis acid respectively.