I2-Mediated transition-metal-free aromatic C–H amination for the synthesis of benzimidazol-2-ones and related heterocycles

A practical iodine-mediated direct aromatic C–H amination reaction has been established for benzimidazol-2-one synthesis under transition-metal-free conditions. The required 1,3-diarylurea substrates are readily accessible by the addition of N-substituted arylamines to the corresponding isocyanates....

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Bibliographic Details
Published inNew journal of chemistry Vol. 42; no. 16; pp. 13790 - 13796
Main Authors Meng, Yinggao, Wang, Bingnan, Ren, Linning, Zhao, Qiongli, Yu, Wenquan, Chang, Junbiao
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 01.01.2018
Subjects
Amines
Chemical synthesis
Iodine
Isocyanates
Organic compounds
Substrates
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Summary:A practical iodine-mediated direct aromatic C–H amination reaction has been established for benzimidazol-2-one synthesis under transition-metal-free conditions. The required 1,3-diarylurea substrates are readily accessible by the addition of N-substituted arylamines to the corresponding isocyanates. This versatile and operationally simple synthetic process is broadly applicable to a wide range of 1,3-diarylureas and provides facile access to benzimidazol-2-ones and related heterocycles. Moreover, the present C–H amination reaction can also be performed directly from disubstituted amines and isocyanates without the purification of the urea intermediates in a scalable fashion.
ISSN:1144-0546
1369-9261
DOI:10.1039/c8nj03166e