Copper-Catalyzed Domino Three-Component Approach for the Assembly of 2-Aminated Benzimidazoles and Quinazolines.

J Org Chem

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, Laboratoire International Associé, CNRS, 91198 Gif-sur-Yvette Cedex, France.

Published: June 2015

AI Article Synopsis

  • A new method has been created to synthesize 2-aminobenzimidazoles or 2-aminoquinazolines using cyanamides, arylboronic acids, and amines.
  • The process is simple and involves oxidative conditions with specific catalysts (CuCl2·2H2O and 2,2'-bipyridine) and K2CO3, conducted under an oxygen atmosphere.
  • This synthesis allows for the quick formation of key compounds by creating three new bonds, including two C-N bonds and one C-H functionalization bond.

Article Abstract

A copper-promoted three-component synthesis of 2-aminobenzimidazoles (1) or of 2-aminoquinazolines (2) involving cyanamides, arylboronic acids, and amines has been developed. The operationally simple oxidative process, performed in the presence of K2CO3, a catalytic amount of CuCl2·2H2O, 2,2'-bipyridine, and an O2 atmosphere (1 atm), allows the rapid assembly of either benzimidazoles or quinazolines starting from aryl- or benzyl-substituted cyanamides, respectively. In this process, the copper promotes the formation of three bonds, two C-N bonds, and an additional bond resulting from C-H functionalization event.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.5b00614DOI Listing

Publication Analysis

Top Keywords

benzimidazoles quinazolines
8
copper-catalyzed domino
4
domino three-component
4
three-component approach
4
approach assembly
4
assembly 2-aminated
4
2-aminated benzimidazoles
4
quinazolines copper-promoted
4
copper-promoted three-component
4
three-component synthesis
4

Similar Publications

Researchers are actively looking for novel anticancer medications because cancer is one of the leading causes of mortality worldwide. A fascinating area of study in medicinal chemistry is the screening of antioxidants for novel anticancer medicines, as antioxidants have lately been used as therapeutic candidates to combat a variety of ailments in aerobic species. Additionally, pyrazole-based heterocycle synthesis is a productive approach to the drug development process.

View Article and Find Full Text PDF

Selected Metal (Au, Ag, and Cu) Complexes of N-heterocyclic Ligands as Potential Anticancer Agents: A Review.

Anticancer Agents Med Chem

January 2025

Department of Pharmaceutics, College of Pharmacy, Jazan University, Saudi Arabia.

Nitrogen-based organic heterocyclic compounds are an important source of therapeutic agents. About 75% of drugs approved by the FDA and currently available in the market are N-heterocyclic organic compounds. The N-heterocyclic organic compounds like pyridine, indole, triazoles, triazine, imidazoles, benzimidazoles, quinazolines, pyrazoles, quinolines, pyrimidines, porphyrin, etc.

View Article and Find Full Text PDF
Article Synopsis
  • The phosphatidylinositol-3 kinase (PI3K) pathway is crucial in various cancers, making it an attractive target for cancer therapies due to its role in cell survival and metastasis.
  • Mutations or overexpression in PI3K genes (PIK3CA, PIK3CB, PIK3CD, PIK3CG) lead to treatment failures, prompting ongoing clinical trials of PI3K inhibitors to combat drug resistance.
  • Many PI3K inhibitors have faced withdrawal due to safety concerns, but research continues on promising compounds with unique scaffolds to improve therapy efficacy and safety.
View Article and Find Full Text PDF

Letermovir and maribavir have demonstrated efficacy in the prevention and treatment, respectively, of immunosuppressed patients with cytomegalovirus (CMV) infection and disease. These patients often have polypharmacy making them at risk for drug-drug interactions. Both letermovir and maribavir can be perpetrators and victims of drug-drug interactions.

View Article and Find Full Text PDF

A critical analysis of design, binding pattern and SAR of benzo-fused heteronuclear compounds as VEGFR-2 inhibitors.

Bioorg Med Chem

December 2024

Drug Design and Synthesis Lab, Department of Pharmaceutical Sciences and Drug Research, Punjabi University, Patiala, India.

Vascular endothelial growth factors (VEGFs) are a class of homodimeric ligands that bind to their receptors (VEGFRs) to carryout physiological and pathological angiogenesis essential for regulating homeostasis of body. Overexpression of VEGF results in metastasis of benign tumor into malignant tumor. An active role of VEGFR-2 in cancer angiogenesis makes it a major target for cancer therapy.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!