Ruthenium(II)-catalyzed remote C-H addition of 8 aminoquinoline amide to activated aldehyde

被引：16

作者：

Mondal, Susmita ^{[1
]}

Hajra, Alakananda ^{[1
]}

机构：

[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 16期

关键词：

CATALYZED OXIDATIVE ANNULATION; BOND ACTIVATION; MILD CONDITIONS; METAL-FREE; 8-AMINOQUINOLINE AMIDES; COUPLING REACTION; QUINOLINES; FUNCTIONALIZATION; ARYLATION; DERIVATIVES;

D O I：

10.1039/c8ob00537k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium(II)-catalyzed regioselective remote C-H addition of 8-aminoquinoline amides at C-5 position to ethyl glyoxalate and 2,2,2-trifluoroacetaldehyde have been developed. The transformation affords C-5 functionalized quinolines in moderate to good yields. This method is applicable to various aryl, heteroaryl as well as aliphatic carboxamides. Experimental results suggest that the reaction very likely proceeds through an ionic pathway.

引用

页码：2846 / 2850

页数：5

共 55 条

[1] Ruthenium-Catalyzed Oxidative Annulation of 6-Anilinopurines with Alkynes via C-H Activation: Synthesis of Indole-Substituted Purines/Purine Nucleosides [J].

Allu, Srinivasarao ;

Swamy, K. C. Kumara .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (12) :2665-2680

[2] Ruthenium-Catalyzed Synthesis of lsoquinolones with 8-Aminoquinoline as a Bidentate Directing Group in C-H Functionalization [J].

Allu, Srinivasarao ;

Swamy, K. C. Kumara .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :3963-3972

[3]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]

[4] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].

Berman, Ashley M. ;

Lewis, Jared C. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+

[5] Carboxylation of C-H Bonds Using N-Heterocyclic Carbene Gold(I) Complexes [J].

Boogaerts, Ine I. F. ;

Nolan, Steven P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) :8858-+

[6] Nickel-Catalyzed Site-Selective C-H Bond Difluoroalkylation of 8-Aminoquinolines on the C5-Position [J].

Chen, Hao ;

Li, Pinhua ;

Wang, Min ;

Wang, Lei .

ORGANIC LETTERS, 2016, 18 (19) :4794-4797

[7] Cobalt-Catalyzed Coupling of Alkyl Grignard Reagent with Benzamide and 2-Phenylpyridine Derivatives through Directed C-H Bond Activation under Air [J].

Chen, Quan ;

Ilies, Laurean ;

Yoshikai, Naohiko ;

Nakamura, Eiichi .

ORGANIC LETTERS, 2011, 13 (12) :3232-3234

[8] Iron-Catalyzed, Chelation-Induced Remote C-H Allylation of Quinolines via 8-Amido Assistance [J].

Cong, Xuefeng ;

Zeng, Xiaoming .

ORGANIC LETTERS, 2014, 16 (14) :3716-3719

[9] Ruthenium-Catalyzed C-N and C-O Bond-Forming Processes from C-H Bond Functionalization [J].

Dana, Suman ;

Yadav, M. Ramu ;

Sahoo, Akhila K. .

C-H BOND ACTIVATION AND CATALYTIC FUNCTIONALIZATION I, 2016, 55 :189-215

[10]

David J. R., 1976, BIOCH GENET, V14, P11

← 1 2 3 4 5 6 →