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

[21] Take the right catalyst:: Palladium-catalyzed C-C, C-N, and C-O bond formation on chloroarenes
Stürmer, R
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (22) : 3307 - 3308
[22] 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
[23] Synthesis of bicyclic lactones via I2-mediated intramolecular tandem C-C/C-O bond formation
Maejima, Saki
Osuka, Mai
Yamaguchi, Eiji
Itoh, Akichika
TETRAHEDRON, 2018, 74 (24) : 2985 - 2990
[24] A Novel Approach for C-C, C-N, and C-O Bond Formation Reactions: A Facile Synthesis of Benzophenazine, Quinoxaline, and Phenoxazine Derivatives via Ring Opening of Benzoxepines
Raju, Bhimapaka China
Prasad, Kasagani Veera
Saidachary, Gannerla
Sridhar, Balasubramanian
ORGANIC LETTERS, 2014, 16 (02) : 420 - 423
[25] Design of palladium (II) methanesulfonate precatalysts for C-C, C-O and C-N cross-coupling reactions
Bruno, Nicholas C.
Tudge, Matthew T.
Buchwald, Stephen L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[26] 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
[27] Consequences of the formation organometallic exciplex [Hg(eta 2-arene)] in mercury-photosensitized reactions of arenes: C-C, C-O, and C-N bond cleavage
Fowley, LA
Lee, JC
Crabtree, RH
Siegbahn, PEM
ORGANOMETALLICS, 1996, 15 (04) : 1157 - 1165
[28] AN ENANTIOSELECTIVE SYNTHESIS OF N-METHYLFUCOSAMINE VIA TANDEM C-C C-O BOND FORMATION
SAMES, D
POLT, R
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16): : 4596 - 4601
[29] AN ENANTIOSELECTIVE SYNTHESIS OF N-METHYLFUCOSAMINE VIA TANDEM C-C/C-O BOND FORMATION
SAMES, D
POLT, R
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 392 - ORGN
[30] BippyPhos: A Highly Versatile Ligand for Pd-Catalyzed C-N, C-O and C-C Couplings
Singer, Robert A.
ISRAEL JOURNAL OF CHEMISTRY, 2020, 60 (3-4) : 294 - 302

← 1 2 3 4 5 →