Metal-Free Cascade Formation of C–C and C–N Bond for the Construction of 3-Cyano-2-Pyridones with Insecticidal Properties

Yao Tang; Nvjiang Wu; Junyu Xu; Xiaopo Zhang; Youbin Li; Xuesong Wang

doi:10.3390/molecules29122792

Molecules (Jun 2024)

Metal-Free Cascade Formation of C–C and C–N Bond for the Construction of 3-Cyano-2-Pyridones with Insecticidal Properties

Yao Tang,
Nvjiang Wu,
Junyu Xu,
Xiaopo Zhang,
Youbin Li,
Xuesong Wang

Affiliations

Yao Tang: Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-Machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Academy of Medical Sciences, Hainan Medical University, Haikou 571199, China
Nvjiang Wu: Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-Machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Academy of Medical Sciences, Hainan Medical University, Haikou 571199, China
Junyu Xu: Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-Machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Academy of Medical Sciences, Hainan Medical University, Haikou 571199, China
Xiaopo Zhang: Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-Machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Academy of Medical Sciences, Hainan Medical University, Haikou 571199, China
Youbin Li: Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-Machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Academy of Medical Sciences, Hainan Medical University, Haikou 571199, China
Xuesong Wang: Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-Machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Academy of Medical Sciences, Hainan Medical University, Haikou 571199, China

DOI: https://doi.org/10.3390/molecules29122792
Journal volume & issue: Vol. 29, no. 12
p. 2792

Abstract

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A straightforward and efficient methodology has been developed for the synthesis of 3-cyano-2-pyridones via the C–C and C–N bond formation processes. A total of 51 diverse 3-cyano-2-pyridone derivatives were obtained in moderate to excellent yields. This reaction featured advantages such as a metal-free process, wide functional group tolerance, simple operation, and mild conditions. A plausible mechanism for the reaction was proposed. 3-cyano-2-pyridones as ricinine analogues for insecticidal properties were evaluated, and the compound 3ci (LC50 = 2.206 mg/mL) showed the best insecticidal property.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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