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Potassium Iodide/ tert ‐Butyl Hydroperoxide‐Mediated Oxidative Annulation for the Selective Synthesis of N ‐Substituted 1,2,3‐Benzotriazine‐4(3 H )‐ones Using Nitromethane as the Nitrogen Synthon
Author(s) -
Yan Yizhe,
Niu Bin,
Xu Kun,
Yu Jianhua,
Zhi Huanhuan,
Liu Yanqi
Publication year - 2016
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.201500619
Subject(s) - chemistry , nitromethane , annulation , synthon , catalysis , oxidative phosphorylation , methyl iodide , iodide , iodine , medicinal chemistry , bond cleavage , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry
A novel and efficient oxidative annulation of 2‐aminobenzamides with nitromethane has been developed for the chemoselective synthesis of N ‐substituted 1,2,3‐benzotriazine‐4(3 H )‐ones in moderate to excellent yields under transition metal‐free conditions. Two NN bonds were constructed in one pot via CN cleavage of nitromethane, which was selectively employed as the nitrogen synthon. The preliminary mechanistic studies revealed that this protocol proceeded under hypoiodite catalysis generated in situ .