POCl₃-mediated synthesis of 2-substituted benzimidazolyl-coumarin, benzimidazolyl-indole, and styrylbenzimidazole derivatives

ABSTRACT

2-Substituted benzimidazolyl heterocycles and styrylbenzimidazoles have been synthesized by the reaction of substituted o-phenylenediamine with different heterocyclic carboxylic acids and cinnamic acid respectively in the presence of POCl₃ as a solvent and catalyst. The proposed reaction has advantageous features of good yields, short reaction times, and operational simplicity. In addition, the scope and limitations were explored, and a plausible reaction mechanism was proposed. The synthesized molecules were characterized by infrared, ¹H NMR, ¹³C NMR, and mass spectral data. Further, single crystals of 2-(1H-indol-2-yl)-1H-benzo[d]imidazole have been developed and structural parameters were collected from x-ray diffraction data.

GRAPHICAL ABSTRACT

KEYWORDS:

• Benzimidazolyl heterocycles
• crystal structure
• 1H-benzimidazoles
• POCl₃

Acknowledgments

The authors acknowledge the University Scientific Instrumentation Centre (USIC), Karnatak University, Dharwad, for SC-XRD and analytical data.