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Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1 H ‐indole Derivatives
Author(s) -
Zhang Xi,
Wang YongQing,
Alduma Anwar L.,
Arif S. H Ullah,
Wang XiCun,
Quan ZhengJun
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000119
Subject(s) - chemistry , aryl , indole test , isocyanide , intramolecular force , combinatorial chemistry , catalysis , selenium , medicinal chemistry , organic chemistry , alkyl
Herein, we report a non‐metal strategy for cyclization reactions of 2‐vinylanilines with/without isonitriles to synthesize 2‐aminoquinoline and 3‐aryl‐1 H ‐indole derivatives. A series of 2‐aminoquinolines were afforded in good to excellent yields in a direct, facile, and efficient approach by Se‐catalyzed isocyanide insertion with 2‐vinylanilines under an air atmosphere. This reaction not only used low toxicity Se as the catalyst, isocyanobenzene substrates were compatible too compared to previous report. Meanwhile, an intramolecular cyclization of 2‐vinylanilines was developed to give 3‐aryl‐1 H ‐indoles in moderate to good yields by using SeO 2 as oxidant.