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Electrochemical Intramolecular Dehydrogenative Coupling of N ‐Benzyl(thio)amides: A Direct and Facile Synthesis of 4 H ‐1,3‐Benzoxazines and 4 H ‐1,3‐Benzothiazines
Author(s) -
Yu Hui,
Jiao Mingdong,
Huang Ruohe,
Fang Xiaowei
Publication year - 2019
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.201801021
Subject(s) - chemistry , electrochemistry , intramolecular force , anode , thio , cathode , combinatorial chemistry , medicinal chemistry , degradation (telecommunications) , stereochemistry , electrode , telecommunications , computer science
The electrochemical dehydrogenative cyclization of N ‐benzylamides was investigated with a Pt plate anode and graphite rod cathode in an undivided cell at room temperature. The oxidative degradation of the products was suppressed successfully and 4 H ‐1,3‐benzoxazines were obtained regardless of the substituents at the benzylic position. This method also allowed for the preparation of 4 H ‐1,3‐benzothiazines.