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New synthesis of 2-benzimidazoleacetates and study of their Knoevenagel reaction

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Abstract

To obtain 2-benzimidazolyl acrylate 2, a new efficient synthesis of 2-benzimidazoleacetate, involving esterification of 2-benzimidazole acetic acid at low temperature as the crucial step, was developed. The generality and efficiency of the process was illustrated by the high-yield synthesis of methyl, ethyl, i-propyl, and n-butyl 2-benzimidazoleacetate. The Knoevenagel reaction of 2-benzimidazoleacetate with aromatic aldehydes was studied. It was found that only in the presence of a catalytic amount of morpholine could the Knoevenagel reaction proceed to give the expected 3-aryl-2-benzimidazolyl acrylate. A mechanism for the morpholine-catalyzed reaction is suggested.

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Acknowledgment

This work was supported by the Natural Science Foundation of the Education Bureau of Shaanxi Province, China (2010JK782) and the Foundation of Xi’an Shiyou University (Z08012).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an, 710065, China

    Peng Hui Yang, Qun Zheng Zhang & Hong Jiang Yu

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  1. Peng Hui Yang
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  2. Qun Zheng Zhang
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  3. Hong Jiang Yu
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Correspondence to Peng Hui Yang.

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Yang, P.H., Zhang, Q.Z. & Yu, H.J. New synthesis of 2-benzimidazoleacetates and study of their Knoevenagel reaction. Res Chem Intermed 38, 1403–1409 (2012). https://doi.org/10.1007/s11164-011-0471-z

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  • DOI: https://doi.org/10.1007/s11164-011-0471-z

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