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

页数：13

共 50 条

[41] Transition-metal-free synthesis of imidazobenzothiazines via domino C-S/C-N bond formation
Tu, Xingzhao
Zhou, Lihong
Li, Zhijie
Lei, Ning
Zeng, Qingle
MONATSHEFTE FUR CHEMIE, 2014, 145 (12): : 1925 - 1931
[42] In Situ Generated 1-Naphthylmethyl Radicals from Bis(1-Naphthylmethyl)tin Dichlorides: Utilization for C-C, C-N, and C-O Bond-Forming Reactions
Dhanwant, Kisturi
Bhedi, Dharmveer
Bhanuchandra, M.
Thirumoorthi, Ramalingam
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (01)
[43] Copper(II) Acetate/Oxygen-Mediated Nucleophilic Addition and Intramolecular C-H Activation/C-N or C-C Bond Formation: One-Pot Synthesis of Benzimidazoles or Quinazolines
He, Hua-Feng
Wang, Zhi-Jing
Bao, Weiliang
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) : 2905 - 2912
[44] Rh(III)-Catalyzed C(8)-H Functionalization of Quinolines via Simultaneous C-C and C-O Bond Formation: Direct Synthesis of Quinoline Derivatives with Antiplasmodial Potential
Sharma, Ritika
Kumar, Rakesh
Kumar, Rohit
Upadhyay, Pooja
Sahal, Dinkar
Sharma, Upendra
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20) : 12702 - 12710
[45] A Domino Palladium-Catalyzed C-C and C-O Bonds Formation via Dual O-H Bond Activation: Synthesis of 6, 6-Dialkyl-6H-benzo[c]chromenes
Mahendar, Lodi
Krishna, Jonnada
Reddy, Alavala Gopi Krishna
Ramulu, Bokka Venkat
Satyanarayana, Gedu
ORGANIC LETTERS, 2012, 14 (02) : 628 - 631
[46] C-N and C-C Bond Formations in the Thermal Reactions of "Bare" Ni(NH2)+ with C2H4: Mechanistic Insight on the Metal-Mediated Hydroamination of an Unactivated Olefin
Kretschmer, Robert
Schlangen, Maria
Schwarz, Helmut
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) : 3483 - 3488
[47] C-C Bond Formation via C-H Activation and C-N Bond Formation via Oxidative Amination Catalyzed by Palladium-Polyoxometalate Nanomaterials Using Dioxygen as the Terminal Oxidant
Chng, Leng Leng
Zhang, Jie
Yang, Jinhua
Amoura, Makhlouf
Ying, Jackie Y.
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 2988 - 2998
[48] A versatile and efficient ligand for copper-catalyzed formation of C-N, C-o, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester
Rao, HH
Jin, Y
Fu, H
Jiang, YY
Zhao, YF
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) : 3636 - 3646
[49] Transition-metal-free Oxidative Coupling Reactions for the Formation of C-C and C-N Bonds Mediated by TEMPO and its Derivatives
Murarka, Sandip
Wertz, Sebastian
Studer, Armido
CHIMIA, 2012, 66 (06) : 413 - 417
[50] Ruthenium(II)-Catalysed sp2 C-H Bond Functionalization by C-C Bond Formation
Li, Bin
Dixneuf, Pierre H.
RUTHENIUM IN CATALYSIS, 2014, 48 : 119 - 193

← 1 2 3 4 5 →