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An Efficient Synthesis of Benzimidazole-Pyrazines Via the Sequential Ugi/Hydroamination/Cyclization Reactions Publisher



Tahmasebi B1 ; Adib M1 ; Mahdavi M2 ; Taslimi P3
Authors
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Authors Affiliations
  1. 1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  2. 2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Department of Biotechnology, Faculty of Science, Bartin University, Bartin, 74100-, Turkey

Source: ChemistrySelect Published:2023


Abstract

This study reported an efficient two-step method based on the sequential post-Ugi hydroamination reaction for synthesizing a novel class of benzimidazole-pyrazines with high yields. First, a Ugi fourcomponent reaction (Ugi-4CR) is carried out using readily available starting materials, i. e., 1H-benzo[d]imidazole-2-carboxylic acid, aldehydes, propargylamine, and isocyanides, in methanol at ambient temperature. Afterward, the Ugi products undergoes a sequential intramolecular hydroamination/cyclization reaction between a nitrogen of imidazole and alkyne functional group in aqua media in the presence of AuCl3 as a catalyst to obtain benzimidazole-pyrazine products. These heterocyclic compounds may have a potential to be utilized in designing modern drugs with desirable features. © 2023 Wiley-VCH Verlag GmbH.