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Synthesis 2024; 56(06): 975-988
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

Sumit K. Singh
,
Sunil Kumar
,
Mangal S. Yadav
,
Subrato Bhattacharya
,
Vinod K. Tiwari  ∗
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).
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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 - triazoles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2157-9001.
  • Supporting Information


Publication History

Received: 06 July 2023

Accepted after revision: 21 August 2023

Accepted Manuscript online:
21 August 2023

Article published online:
10 October 2023

© 2023. Thieme. All rights reserved

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