Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes

被引：158

作者：

Zheng, Liyao ^{[1
]}

Ju, Jia ^{[1
]}

Bin, Yunhui ^{[1
]}

Hua, Ruimao ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Organ Optoelect & Mol Engn, Minist Educ, Beijing 100084, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 13期

基金：

中国国家自然科学基金;

关键词：

PALLADIUM-CATALYZED IMINOANNULATION; ONE-POT SYNTHESIS; H BOND ACTIVATION; C-H; INTERNAL ALKYNES; ALPHA; BETA-UNSATURATED KETOXIMES; RHODIUM(III)-CATALYZED SYNTHESIS; ELECTROPHILIC CYCLIZATION; GAMMA-CARBOLINES; BETA-CARBOLINES;

D O I：

10.1021/jo3010414

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C-H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of multisubstituted isoquinolines as well as gamma-carbolines; furo[2,3-c]pyridines, thieno[2,3-c]pyridines, and benzofuro[2,3-c]pyridines from readily available substrates.

引用

页码：5794 / 5800

页数：7

共 65 条

[1]

[Anonymous], 2003, CHEM HETEROCYCLES ST, DOI DOI 10.1002/352760183X

[2] Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis [J].

Chen, C ;

Li, XD ;

Schreiber, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10174-10175

[3] TSPO 18 kDa (PBR) Targeted Photosensitizers for Cancer Imaging (PET) and PDT [J].

Chen, Yihui ;

Sajjad, Munawwar ;

Wang, Yanfang ;

Batt, Carrie ;

Nabi, Hani A. ;

Pandey, Ravindra K. .

ACS MEDICINAL CHEMISTRY LETTERS, 2011, 2 (02) :136-141

[4] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[5] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[6] Diphenyl quinolines and isoquinolines: Synthesis and primary biological evaluation [J].

Croisy-Delcey, M ;

Croisy, A ;

Carrez, D ;

Huel, C ;

Chiaroni, A ;

Ducrot, P ;

Bisagni, E ;

Jin, L ;

Leclercq, G .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (11) :2629-2641

[7] Multi-component syntheses of heterocycles by transition-metal catalysis [J].

D'Souza, Daniel M. ;

Mueller, Thomas J. J. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108

[8] Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C-H Bond Cleavage Using Dioxygen as Oxidant [J].

Ding, Shengtao ;

Shi, Zhuangzhi ;

Jiao, Ning .

ORGANIC LETTERS, 2010, 12 (07) :1540-1543

[9] Chemistry and Biology Of Multicomponent Reactions [J].

Domling, Alexander ;

Wang, Wei ;

Wang, Kan .

CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135

[10] Sterically non-hindering endocyclic ligands of the bi-isoquinoline family [J].

Durola, F ;

Sauvage, JP ;

Wenger, OS .

CHEMICAL COMMUNICATIONS, 2006, (02) :171-173

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