Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share By
An Efficient Synthesis of Benzimidazole-Pyrazines Via the Sequential Ugi/Hydroamination/Cyclization Reactions Publisher



Tahmasebi B1 ; Adib M1 ; Mahdavi M2 ; Taslimi P3
Authors

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.
Related Docs
View other Related Docs
1. Potassium Carbonate Catalyzed Intramolecular Post-Ugi Hydroamination Reaction Leading to N -Aryl Piperazine Derivatives, Synlett (2025)
2. Synthesis, Reaction and Biological Activity of Pyrazolo[5,1-C][1,2,4]Benzotriazine 5-Oxides, Politics and Religion Journal (2018)
3. Synthesis, Characterization and Biological Evaluation of Novel 3-Methyl-5-Pyrazolone Derivatives, Journal of Medicinal and Chemical Sciences (2021)
Experts (# of related papers)
View all Related Experts
Mohammad Mahdavi (16)
Mina Saeedi (5)
Other Related Docs
4. Construction of [1,4]Oxazepin-2-Ones Via Catalyst-Free Intramolecular C–O Bond Formation From Ugi Adducts, Tetrahedron Letters (2024)
5. Potassium T-Butoxide-Promoted Metal-Free Synthesis of Pyrazino[1,2-A]Indoles Via Direct Amidation and Intramolecular Hydroamination Reaction, ChemistrySelect (2023)
6. Ugi Four-Multicomponent Reaction Based Synthesis, in Vitro, and in Silico Enzymatic Evaluations of New Pyrazino[1,2-A]Indole-1,4-Dione-Indole-2-Phenylacetamides As Potent Inhibitors Against Α-Glucosidase and Α-Amylase, Chemistry and Biodiversity (2024)
7. Design, Synthesis and Antibacterial Activity Evaluation of Novel 2-(4-((1-Aryl-1H-1,2,3-Triazol-4-Yl)Methoxy)Phenyl)2-(2-Oxoazetidin-1-Yl)Acetamide Derivatives, Journal of Heterocyclic Chemistry (2020)
8. Synthesis of Novel Pyrazino[2,1-A]Isoindolediones Via Intramolecular Hydroamination of 2,3-Dihydro-3-Oxo-2-(Prop-2-Yn-1-Yl)-1H-Isoindole-1-Carboxamides, Helvetica Chimica Acta (2016)
9. Efficient Synthesis of Chromeno[4,3-B]Pyrano[3,4-E]Pyridine-6,8-Dione Derivatives Via Multicomponent One-Pot Reaction Under Mild Reaction Conditions in Water, Research on Chemical Intermediates (2021)
10. Synthesis of Piperazine-Based Benzimidazole Derivatives As Potent Urease Inhibitors and Molecular Docking Studies, Scientific Reports (2025)
11. N-Cyclohexylimidazo[1,2-A]Pyridine Derivatives As Multi-Target-Directed Ligands for Treatment of Alzheimer's Disease, Bioorganic Chemistry (2020)
12. Novel and Efficient Synthesis of Triazolobenzodiazepine Analogues Through the Sequential Ugi 4Cr-Click-N-Arylation Reactions, Tetrahedron Letters (2019)
13. Iodine-Mediated Synthesis of Novel Pyrazole Derivatives, Synthesis (Germany) (2016)
14. Developments in Organocatalysis Transformations of Unsaturated Pyrazolones, Current Organic Synthesis (2025)
15. Post-Ugi Cyclization Approach for Transition Metal-Free Synthesis of Azetidine Derivatives, Tetrahedron Letters (2025)
16. Triarylpyrazole Derivatives As Potent Cytotoxic Agents; Synthesis and Bioactivity Evaluation Pyrazole Derivatives As Anticancer Agent, Drug Research (2021)
17. Synthesis and Cytotoxic Activity of Novel Poly-Substituted Imidazo[2,1-C][1,2,4]Triazin-6-Amines, Molecular Diversity (2015)
18. Experimental and Computational Evidence for Kot-Bu-Promoted Synthesis of Oxopyrazino[1,2-A]Indoles, RSC Advances (2015)
19. Antiproliferative Activity of New Derivatives of Pyrazino[1,2-A]Benzimidazole: Integrated Cell-Based Assay and Computational Studies With Divalent Magnesium, Iron, and Copper Ions, Journal of Biochemical and Molecular Toxicology (2022)
20. An Efficient and Targeted Synthetic Approach Towards New Highly Substituted 6-Amino-Pyrazolo[1,5-A]Pyrimidines With Α-Glucosidase Inhibitory Activity, Scientific Reports (2020)