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Synthesis 2024; 56(06): 975-988
DOI: 10.1055/a-2157-9001
DOI: 10.1055/a-2157-9001
paper
Emerging Trends in Glycoscience
Glycosyl Triazole Based Pyridinamide/CuI-Catalyzed Coupling of 2-Halobenzamides with Active Methylene Compounds
The authors sincerely thank the Science and Engineering Research Board (SERB), New Delhi (Grant No.: CRG/2021/002776) and the Council of Scientific and Industrial Research (CSIR), New Delhi, India (Scheme No. 02(0345)/19/EMR-II) for financial support. The authors also gratefully acknowledge the Institute of Eminence (IOE), Banaras Hindu University for an incentive grant. MSY and SK acknowledge the CSIR, New Delhi for fellowships (SRF).
Abstract
This report describes a convenient method for the Cu(I)-catalyzed tandem synthesis of dihydrophenanthridinediones and substituted isoquinolinones with the assistance of efficient glycosyl 1,2,3-triazole-based pyridinamide ligands. The catalytic system effectively works for the coupling of N-substituted 2-halobenzamides with various active methylene compounds to form biologically relevant heterocyclic scaffolds in high to excellent yields. The consecutive path of the reaction including intermolecular C–C cross-coupling followed by intramolecular cyclization efficiently takes place at low catalytic loading. These glycosyl triazole-appended pyridinamides were synthesized in good yields by a CuI/DIPEA-mediated regioselective CuAAC click reaction. The notable features of the method include low catalytic loading, the use of cost-effective and biocompatible ligands, high reaction yield, and easily accessible starting materials that make the protocol more versatile.
Key words
carbohydrates - copper catalysis - CuAAC click reaction - cross-coupling - glycohybrids - triazolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2157-9001.
- Supporting Information
Publikationsverlauf
Eingereicht: 06. Juli 2023
Angenommen nach Revision: 21. August 2023
Accepted Manuscript online:
21. August 2023
Artikel online veröffentlicht:
10. Oktober 2023
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