Issue 20, 2019
From the journal:

Organic & Biomolecular Chemistry

Selective synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o-phenylenediamine†

Zhenzhen Zhan,a   Haojie Ma,a   Xinfeng Cui,a   Pengbo Jiang,a   Jinghong Pu,a   Yixin Zhanga  and  Guosheng Huang ORCID logo *a  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, Department of Chemistry, Lanzhou University, Lanzhou, P. R. China
E-mail: hgs@lzu.edu.cn

Abstract

We have designed a general, inexpensive, and versatile method for the synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and the formation of C–N bonds via an aromatic aldehyde and o-phenylenediamine. In the presence of N,N-dimethylformamide/sulfur, (1H-benzo[d]imidazol-2-yl)(phenyl)methanone was obtained; however, in the absence of sulfur, quinoxaline was obtained in 1,4-dioxane. A wide range of quinoxalines and (1H-benzo[d]imidazol-2-yl)(phenyl)methanones was obtained under mild conditions.

Graphical abstract: Selective synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o-phenylenediamine

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Article information

DOI
https://doi.org/10.1039/C9OB00531E
Article type
Paper
Submitted
04 Mar 2019
Accepted
24 Apr 2019
First published
24 Apr 2019

Org. Biomol. Chem., 2019,17, 5148-5152

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Selective synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o-phenylenediamine

Z. Zhan, H. Ma, X. Cui, P. Jiang, J. Pu, Y. Zhang and G. Huang, Org. Biomol. Chem., 2019, 17, 5148 DOI: 10.1039/C9OB00531E

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