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Facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride

BACKGROUND: We report the synthesis of benzimidazoles using lanthanum chloride as an efficient catalyst. One-pot synthesis of 2-substituted benzimidazole derivatives from o-phenylenediamine and a variety of aldehydes were developed under mild reaction conditions. RESULTS: We have examined the effect...

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Autores principales: Venkateswarlu, Yekkirala, Kumar, Sudhagani Ramesh, Leelavathi, Panuganti
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3765254/
https://www.ncbi.nlm.nih.gov/pubmed/23919542
http://dx.doi.org/10.1186/2191-2858-3-7
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author Venkateswarlu, Yekkirala
Kumar, Sudhagani Ramesh
Leelavathi, Panuganti
author_facet Venkateswarlu, Yekkirala
Kumar, Sudhagani Ramesh
Leelavathi, Panuganti
author_sort Venkateswarlu, Yekkirala
collection PubMed
description BACKGROUND: We report the synthesis of benzimidazoles using lanthanum chloride as an efficient catalyst. One-pot synthesis of 2-substituted benzimidazole derivatives from o-phenylenediamine and a variety of aldehydes were developed under mild reaction conditions. RESULTS: We have examined the effect of different solvents using the same reaction conditions. The yield of the product varied with the nature of the solvents, and better conversion and easy isolation of products were found with acetonitrile. In a similar manner, the reaction with o-phenylenediamine and 3,4,5-trimethoxybenzaldehyde was carried out without any solvents. The observation shows that the reaction was not brought into completion, even after starting for a period of 9 h, and the reaction mixture showed a number of spots in thin-layer chromatography. CONCLUSIONS: In conclusion, lanthanum chloride has been employed as a novel and efficient catalyst for the synthesis of benzimidazoles in good yields from o-phenylenediamine and a wide variety of aldehydes. All of the reactions were carried out in the presence of lanthanum chloride (10 mol%) in acetonitrile at room temperature.
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spelling pubmed-37652542013-09-10 Facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride Venkateswarlu, Yekkirala Kumar, Sudhagani Ramesh Leelavathi, Panuganti Org Med Chem Lett Original Article BACKGROUND: We report the synthesis of benzimidazoles using lanthanum chloride as an efficient catalyst. One-pot synthesis of 2-substituted benzimidazole derivatives from o-phenylenediamine and a variety of aldehydes were developed under mild reaction conditions. RESULTS: We have examined the effect of different solvents using the same reaction conditions. The yield of the product varied with the nature of the solvents, and better conversion and easy isolation of products were found with acetonitrile. In a similar manner, the reaction with o-phenylenediamine and 3,4,5-trimethoxybenzaldehyde was carried out without any solvents. The observation shows that the reaction was not brought into completion, even after starting for a period of 9 h, and the reaction mixture showed a number of spots in thin-layer chromatography. CONCLUSIONS: In conclusion, lanthanum chloride has been employed as a novel and efficient catalyst for the synthesis of benzimidazoles in good yields from o-phenylenediamine and a wide variety of aldehydes. All of the reactions were carried out in the presence of lanthanum chloride (10 mol%) in acetonitrile at room temperature. Springer 2013-08-06 /pmc/articles/PMC3765254/ /pubmed/23919542 http://dx.doi.org/10.1186/2191-2858-3-7 Text en Copyright ©2013 Venkateswarlu et al.; licensee Springer. http://creativecommons.org/licenses/by/2.0 This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Original Article
Venkateswarlu, Yekkirala
Kumar, Sudhagani Ramesh
Leelavathi, Panuganti
Facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride
title Facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride
title_full Facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride
title_fullStr Facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride
title_full_unstemmed Facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride
title_short Facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride
title_sort facile and efficient one-pot synthesis of benzimidazoles using lanthanum chloride
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3765254/
https://www.ncbi.nlm.nih.gov/pubmed/23919542
http://dx.doi.org/10.1186/2191-2858-3-7
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