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One‐Pot Synthesis of Quinazolin‐4(3 H )‐ones through Anodic Oxidation and the Related Mechanistic Studies
Author(s) -
Cao Liu,
Huo Hengrui,
Zeng Haipeng,
Yu Yu,
Lu Dengfu,
Gong Yuefa
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.201800927
Subject(s) - chemistry , combinatorial chemistry , environmentally friendly , electrolysis , annulation , electrochemistry , anodic oxidation , catalysis , organic chemistry , electrode , ecology , electrolyte , biology
A metal‐free and oxidant‐free method for the one‐pot preparation of quinazolin‐4( 3H )‐ones enabled by electrochemical oxidation is described. Together with 2‐aminobenzamides, a variety of aldehydes were successfully applied to an acid‐catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline‐4( 3H )‐ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin‐4( 3H )‐ones, the synthetic utility of this method was demonstrated by gram‐scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib.