Metal-Free Cascade Formation of C–C and C–N Bond for the Construction of 3-Cyano-2-Pyridones with Insecticidal Properties-Reference-Cited by-同舟云学术

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

Published:2024-06-12 Issue:12 Volume:29 Page:2792
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Tang Yao¹,Wu Nvjiang¹,Xu Junyu¹,Zhang Xiaopo¹,Li Youbin¹,Wang Xuesong¹^ORCID

Affiliation:

1. 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

Abstract

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.

Funder

Hainan Provincial Association for Science and Technology Youth Science and Technology Talent Innovation Program

National Natural Science Foundation of China

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/12/2792/pdf

Reference77 articles.

1. Fredericamycin A, an Antitumor Antibiotic of a Novel Skeletal Type;Misra;J. Am. Chem. Soc.,1982

2. Pyridones as Highly Selective, Noncovalent Inhibitors of T790M Double Mutants of EGFR;Bryan;ACS Med. Chem. Lett.,2016

3. Six Years (2012–2018) of Researches on Catalytic Ezh2 Inhibitors: The Boom of the 2-Pyridone Compounds;Fioravanti;Chem. Rec.,2018

4. Structure–Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 6. Structure-Activity Studies of Orally Bioavailable, 2-Pyridone-Containing Peptidomimetics;Dragovich;J. Med. Chem.,2002

5. Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (Perampanel): A Novel, Noncompetitive α-Amino-3-hydroxy-5-methyl-4-isoxazolepropanoic Acid (AMPA) Receptor Antagonist;Hibi;J. Med. Chem.,2012