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Synthesis of 1H-1,3-benzimidazoles, benzothiazoles and 3H-imidazo[4,5-c]pyridine using DMF in the presence of HMDS as a reagent under the transition-metal-free condition

Hamid Mostafavi, Mohammad Reza Islami, Ehsan Ghonchepour, and Ahmad Momeni Tikdari

Shahid Bahonar University of Kerman, Kerman, Iran

 

E-mail: mrislami@uk.ac.ir

Abstract: An operationally simple method for synthesis of benzimidazole and 3H-imidazo[4,5-c]pyridine from o-phenylenediamine or pyridine-3, 4-diamine and N,N-dimethylformamide (DMF) in the presence of hexamethyldisilazane (HMDS) as a reagent is described. To evaluate the scope of application of this reagent, it was also used to prepare benzothiazole, 1H-perimidine, and benzoxazole, which was successful for benzothiazole and 1H-perimidine but benzoxazole was not formed. This reaction complies with the principles of green chemistry as it does not use toxic solvents, transition metals, or strong acids. The products are obtained in moderate to excellent yields.

Keywords: Benzimidazole ; Heterocyclic compounds ; HMDS ; DMF ; Biological activities 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-018-0540-5

 

Chemical Papers 72 (12) 2973–2978 (2018)

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