Benzoxanthenes and their analogues are a very important class of compounds mainly due to their wide range of biological and technological applications. The development of a new methodology for their synthesis, involving an Ullmann-type coupling followed by an intramolecular C-H arylation, catalyzed by copper in a domino fashion, is reported. A variety of -substituted phenols are amenable to this methodology, affording the desired products in moderate to good yields. Our protocol is expedient and practical and is carried out under microwave irradiation in only 3 min under air. A plausible catalytic cycle is proposed based on experimental mechanistic investigations and density functional theory (DFT) calculations.
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http://dx.doi.org/10.1021/acs.joc.3c00830 | DOI Listing |
Bioorg Chem
January 2025
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India; Glycochemistry Laboratory, School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India. Electronic address:
Molecular hybridization is an emerging strategy in medicinal chemistry for designing new bioactive molecules that link pharmacophores covalently and shows synergistic enhanced properties. Herein, we have developed pyrazolo[3,4-b]pyridine-based new glycohybrids considering the Warburg effect. A microwave-assisted, copper-catalyzed efficient synthesis of new triazole-linked glycohybrids based on pyrazolo[3,4-b]pyridines scaffold was achieved successfully in high yields with inherent stereochemical diversity from d-glucose, d-galactose, and d-mannose.
View Article and Find Full Text PDFBioorg Med Chem
October 2024
Department of Microbiology, University of Ilorin, Ilorin, Nigeria.
In this dispensation of rapid scientific and technological advancements, significant efforts are being made to curb health-related diseases. Research discoveries have highlighted the value of heterocyclic compounds, particularly thiadiazole derivatives, due to their diverse pharmacological activities. These compounds play a crucial role in therapeutic medicine and the development of effective drugs.
View Article and Find Full Text PDFSci Rep
January 2024
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India.
Hybrid molecules maintain their stronghold in the drug market, with over 60% of drug candidates in pharmaceutical industries. The substantial expenses for developing and producing biologically privileged drugs are expected to create opportunities for producing hybrid molecule-based drugs. Therefore, we have developed a simple and efficient copper-catalyzed approach for synthesizing a wide range of triazole-linked glycohybrids derived from pyrazolo[1,5-a]pyrimidines.
View Article and Find Full Text PDFRSC Adv
September 2023
Center of Excellence in Cannabis Research, Faculty of Pharmaceutical Sciences, Naresuan University Phitsanulok 65000 Thailand
A facile and green one-pot synthesis of AChE quinazolinone inhibitors was developed using microwave irradiation under solvent free conditions. Quinazolinones were synthesized from 2-aminobenzamide derivatives and various alcohols such as benzyl alcohol derivatives and butanol using economical commercially available copper as a catalyst in the presence of base, CsCO. The desired products were achieved in moderate to high yields with up to 92% isolated yield.
View Article and Find Full Text PDFJ Org Chem
August 2023
Department of Chemistry, National and Kapodistrian University of Athens Panepistimiopolis, 15771 Athens, Greece.
Benzoxanthenes and their analogues are a very important class of compounds mainly due to their wide range of biological and technological applications. The development of a new methodology for their synthesis, involving an Ullmann-type coupling followed by an intramolecular C-H arylation, catalyzed by copper in a domino fashion, is reported. A variety of -substituted phenols are amenable to this methodology, affording the desired products in moderate to good yields.
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