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Copper‐Catalyzed Domino Reactions for the Synthesis of Phenothiazines
Author(s) -
Huang Manna,
Huang Dongting,
Zhu Xinhai,
Wan Yiqian
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500667
Subject(s) - chemistry , domino , catalysis , copper , aryl , combinatorial chemistry , ligand (biochemistry) , coupling reaction , organic chemistry , biochemistry , alkyl , receptor
A method for the one‐pot synthesis of phenothiazines from benzothiazoles and aryl ortho ‐dihalides was explored. Preliminary work on the mechanism of the reaction suggested that it follows a domino process, including the hydrolysis of benzothiazoles followed by C–S coupling and C–N coupling. The low loading of the catalyst system (5 mol‐% for both copper and ligand), the mild experimental conditions (90 °C, 12 h), and the use of a green reaction medium make this synthesis very attractive to academia and industry.