Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles

The synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles is described via intramolecular cyclization of o-bromoaryl derivatives using copper(II) oxide nanoparticles in DMSO under air. The procedure is experimentally simple, general, efficient, and f...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-11, Vol.74 (22), p.8719-8725
Main Authors: Saha, Prasenjit, Ramana, Tamminana, Purkait, Nibadita, Ali, Md Ashif, Paul, Rajesh, Punniyamurthy, Tharmalingam
Format: Article
Language:English
Subjects:
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Benzoxazoles - chemical synthesis
Benzoxazoles - chemistry
Catalysis
Chemistry
Copper - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Ligands
Molecular Structure
Nanoparticles - chemistry
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:The synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles is described via intramolecular cyclization of o-bromoaryl derivatives using copper(II) oxide nanoparticles in DMSO under air. The procedure is experimentally simple, general, efficient, and free from addition of external chelating ligands. It is a heterogeneous process and the copper(II) oxide nanoparticles can be recovered and recycled without loss of activity.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901813g