Abstract
The condensation of O-phenylenediamine (OPD) with aryl aldehydes is carried out in acetonitrile using poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide) (PBNS) as a novel and heterogeneous catalyst. PBNS has some potential advantages which include ease of separation from the reaction mixture by simple filtration, easy preparation, recoverablility, convenience, and stability under normal condition and also is not dangerous as molecular bromine.
Highlights
Polymeric reagents are referred to as the reactive species which are tied or fastened to a polymeric backbone
In continuation of our studies on application of N-halo compounds in organic synthesis [3,4,5, 21] and to explore new approaches toward the heterocyclic compounds, we have used an efficient protocol for the preparation of benzimidazoles catalyzed by PBNS as a novel reagent (Scheme 1)
PBNS was synthesized by covalent attachment of poly(Nethylnaphthyl-2,7-disulfonamide) and molecular bromine (Scheme 2)
Summary
Polymeric reagents are referred to as the reactive species which are tied or fastened to a polymeric backbone These reagents have both the physical characteristics of the high polymer and the chemical characteristics of the attached reagent function. N-Bromo compounds are inexpensive and nonhazardous reagents and they are widely applicable in industrial processes for the synthesis of drugs, pharmaceuticals, and agrochemicals [6]. In this presented work, we synthesize the novel polymer, namely, poly(N,N-dibromo-N-ethylnaphthyl-2,7disulfonamide) (PBNS). The condensation of an arylene diamine with a carboxylic acid or its derivative under harsh dehydrating reaction conditions is the most popular synthesis of these materials [10, 11]. In this work we have reported PBNS as a novel, heterogeneous, and reusable catalyst for the condensation of O-phenylenediamine (OPD) with aryl aldehydes to give corresponding 2-arylbenzimidazoles and 2aryl-1-arylmethyl-1H-1,3-benzimidazoles
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