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One‐Pot Copper‐Catalyzed Cascade Bicyclization Strategy for Synthesis of 2‐(1 H ‐Indol‐1‐yl)‐4,5‐dihydrothiazoles and 2‐(1 H ‐Indol‐1‐yl)thiazol‐5‐yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
Author(s) -
Xie Jialin,
Guo Zhonglin,
Huang Yuanqiong,
Qu Yi,
Song Hongjian,
Song Haibin,
Liu Yuxiu,
Wang Qingmin
Publication year - 2019
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.201801193
Subject(s) - chemistry , hydroamination , intramolecular force , moiety , combinatorial chemistry , catalysis , ketone , aryl , cascade reaction , copper , cascade , stereochemistry , medicinal chemistry , organic chemistry , alkyl , chromatography
An atom‐economical method for synthesizing N ‐heterocyclic indoles from readily available o ‐alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper‐catalyzed cascade bicyclization process consisting of an intramolecular 5‐ exo‐dig hydrothiolation reaction and an intramolecular hydroamination reaction and, depending on whether or not molecular oxygen is present, selectively affords Z ‐isomers of 2‐(1 H ‐indol‐1‐yl)‐4,5‐dihydrothiazoles or 2‐(1 H ‐indol‐1‐yl)thiazol‐5‐yl aryl ketones in satisfactory yields. Mechanistic studies indicate that molecular oxygen acts as the oxygen source for the ketone moiety in the products.