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Bentonite clay: an efficient catalyst for the synthesis of 2-substituted benzimidazoles

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Abstract

Benzimidazoles have been reported to have a wide range of biological and therapeutic properties. For this reason a variety of methods for their synthesis has been described, following one of the two general routes: the coupling of o-phenylenediamine and carboxylic acids or their derivatives using a strong acid and high temperature, or a two-step sequence that involves oxidative cyclodehydrogenation of Schiff’s bases, obtained by the reaction of o-phenylenediamines and aromatic aldehydes. A simple, efficient, and environmentally friendly procedure for the synthesis of substituted 2- and 2,5(6)-substituted benzimidazoles is herein described. The procedure is carried out by treatment of o-phenylenediamine or 4-chloro-o-phenylenediamine with aryl or heteroaryl aldehydes. Bentonite clay is used as catalyst in dry acetonitrile at room temperature. This procedure has several important advantages, including short reaction times, large-scale preparations, easy isolation of the products, and good to excellent yields.

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Acknowledgments

Financial support from IPN México through Grants SIP 20120756, SIP 20130724 is gratefully acknowledged. We thank Javier Peralta Cruz, Ma. de los Ángeles Peña, Beatriz Quiroz, Elizabeth Huerta, Héctor Ríos (NMR), Daniel Arrieta Baes, Luis Velasco (MS), and Marisela Gutiérrez Franco (IR) for analytical support. Héctor Salgado Zamora and Rogelio Jiménez Juárez are fellows of the COFAA and EDI fellowship programs of the IPN. Victor A. Cardozo thanks IPN for a PIFI scholarship. We thank Bruce Allan Larsen for reviewing the use of English in the manuscript.

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Authors and Affiliations

  1. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N, 11340, Mexico D.F., Mexico

    Victor A. Cardozo, Héctor Salgado-Zamora & Rogelio Jiménez-Juárez

  2. Instituto de Química, UNAM, Coyoacán, 04510, Mexico D.F., Mexico

    Rubén Sánchez-Obregón

Authors
  1. Victor A. Cardozo
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  2. Rubén Sánchez-Obregón
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  3. Héctor Salgado-Zamora
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  4. Rogelio Jiménez-Juárez
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Corresponding author

Correspondence to Rogelio Jiménez-Juárez.

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Cardozo, V.A., Sánchez-Obregón, R., Salgado-Zamora, H. et al. Bentonite clay: an efficient catalyst for the synthesis of 2-substituted benzimidazoles. Monatsh Chem 146, 1335–1337 (2015). https://doi.org/10.1007/s00706-015-1423-x

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  • DOI: https://doi.org/10.1007/s00706-015-1423-x

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