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

New synthesis of 2-benzimidazoleacetates and study of their Knoevenagel reaction 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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

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Publisher
Springer Netherlands
Copyright
Copyright © 2011 by Springer Science+Business Media B.V.
Subject
Chemistry; Inorganic Chemistry; Catalysis; Physical Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-011-0471-z
Publisher site
See Article on Publisher Site

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Dec 27, 2011

References

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