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Synthesis 2015; 47(10): 1390-1398
DOI: 10.1055/s-0034-1380154
DOI: 10.1055/s-0034-1380154
paper
One-Pot Synthesis of Highly Functionalized Benzimidazolylisophthalates and (2E)-2-Ethylidene-(1H)-pyridinecarboxylates by Ultrasound-Promoted Multicomponent Reactions
Further Information
Publication History
Received: 18 November 2014
Accepted after revision: 15 January 2015
Publication Date:
04 March 2015 (online)
Abstract
Reaction of 3-formylchromones, 2-aminobenzimidazole, and acetonedicarboxylates under ultrasound irradiation afforded alkyl 2-(1H-benzimidazol-2-ylamino)-5-(2-hydroxyaroyl)isophthalates as the only reaction product in almost quantitative yields. However, when 2-aminobenzimidazole was replaced by aromatic amines novel alkyl 1-aryl-2-[(E)-2-alkoxy-2-oxoethylidene]-5-(2-hydroxyaroyl)-(1H)-pyridine-3-carboxylates were isolated in good yields. A plausible mechanistic scheme for the formation of the isolated isophthalates and pyridine carboxylates is proposed, and full assignment of all their 1H and 13C NMR chemical shifts has been unambiguously achieved. In addition, the lipid peroxidation inhibition of the novel isophthalate derivatives was evaluated, and it was found that one such derivative presents an interesting antilipid peroxidation activity.
Key words
acetonedicarboxylates - 2-aminobenzimidazole - aroylpyridines - benzophenones - 3-formylchromonesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380154.
- Supporting Information
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