2-Bromopyridines as Versatile Synthons for Heteroarylated 2-Pyridones via Ru(II)-Mediated Domino C-O/C-N/C-C Bond Formation Reactions

被引：0
作者：
Drev, Miha [1 ]
Brodnik, Helena [1 ]
Groselj, Uros [1 ]
Perdih, Franc [1 ]
Svete, Jurij [1 ]
Stefane, Bogdan [1 ]
Pozgan, Franc [1 ]
机构：
[1] Univ Ljubljana, Fac Chem & Chem Technol, Vecna Pot 113, Ljubljana 1000, Slovenia
来源：
MOLECULES | 2024年 / 29卷 / 18期
关键词：
ruthenium catalysis; heterocycles; C-H activation; pyridones; 2-bromopyridines; DIRECT ALKYLATION; H ALKYLATION; ARYLATION; PYRIDONES; HETEROCYCLES; ACTIVATION; CHEMISTRY; DIENES;
D O I：
10.3390/molecules29184418
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A novel methodology for the synthesis of 2-pyridones bearing a 2-pyridyl group on nitrogen and carbon atoms, starting from 2-bromopyridines, was developed employing a simple Ru(II)-KOPiv-Na2CO3 catalytic system. Unsubstituted 2-bromopyridine was successfully converted to the penta-heteroarylated 2-pyridone product using this method. Preliminary mechanistic studies revealed a possible synthetic pathway leading to the multi-heteroarylated 2-pyridone products, involving consecutive oxygen incorporation, a Buchwald-Hartwig-type reaction, and C-H bond activation.
引用
收藏
页数：13
相关论文
共 50 条
  • [1] Copper-catalyzed Oxidative C-C, C-O, and C-N Bond Forming Reactions of Arylboronic Acids
    Shirakawa, Eiji
    Nishikawa, Ryo
    Uchiyama, Nanase
    Hata, Ippei
    Hayashi, Tamio
    CHEMISTRY LETTERS, 2013, 42 (03) : 269 - 271
  • [2] Highly Efficient Cyclization Approach of Propargylated Peptides via Gold(I)-Mediated Sequential C-N, C-O, and C-C Bond Formation
    Vanjari, Rajeshwer
    Eid, Emad
    Vamisetti, Ganga B.
    Mandal, Shaswati
    Brik, Ashraf
    ACS CENTRAL SCIENCE, 2021, 7 (12) : 2021 - 2028
  • [3] Formation and evolution of C-C, C-O, C=O and C-N bonds in chemical reactions of prebiotic interest
    Arias, Alejandro
    Gomez, Sara
    Rojas-Valencia, Natalia
    Nunez-Zarur, Francisco
    Cappelli, Chiara
    Murillo-Lopez, Juliana A.
    Restrepo, Albeiro
    RSC ADVANCES, 2022, 12 (44) : 28804 - 28817
  • [4] Ru(ii)-Catalyzed C6-selective C-H amidation of 2-pyridones
    Zhang, Lei
    Zheng, Xiangyun
    Chen, Jinkang
    Cheng, Kang
    Jin, Licheng
    Jiang, Xinpeng
    Yu, Chuanming
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (20): : 2969 - 2973
  • [5] Cu(II)-Mediated C-C/C-O Bond Formation via C-H/C-C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group
    Yu, Shuling
    Lv, Ningning
    Liu, Zhanxiang
    Zhang, Yuhong
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (01) : 118 - 125
  • [6] Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions
    Monnier, Florian
    Taillefer, Marc
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) : 6954 - 6971
  • [7] Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C-N, C-C, and C-O Bond Formations
    Wu, Xingxing
    Hao, Lin
    Zhang, Yuexia
    Rakesh, Maiti
    Reddi, Rambabu N.
    Yang, Song
    Song, Bao-An
    Chi, Yonggui Robin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) : 4201 - 4205
  • [8] Practical palladium catalysts for C-N and C-O bond formation
    Muci, AR
    Buchwald, SL
    CROSS-COUPLING REACTIONS: A PRACTICAL GUIDE, 2002, 219 : 131 - 209
  • [9] Metal-Free Cascade Formation of C-C and C-N Bond for the Construction of 3-Cyano-2-Pyridones with Insecticidal Properties
    Tang, Yao
    Wu, Nvjiang
    Xu, Junyu
    Zhang, Xiaopo
    Li, Youbin
    Wang, Xuesong
    MOLECULES, 2024, 29 (12):
  • [10] Organozinc-Mediated Direct C-C Bond Formation via C-N Bond Cleavage of Ammonium Salts
    Wang, Dong-Yu
    Morimoto, Koki
    Yang, Ze-Kun
    Wang, Chao
    Uchiyama, Masanobu
    CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (19) : 2554 - 2557
12345