Synthesis of (2-oxoindolin-3-ylidene)methyl acetates involving a C-H functionalization process

被引：86

作者：

Tang, Shi ^{[1
,3
]}

Peng, Peng ^{[1
]}

Wang, Zhi-Qiang ^{[1
]}

Tang, Bo-Xiao ^{[1
]}

Deng, Chen-Liang ^{[1
]}

Li, Jin-Heng ^{[1
,2
]}

Zhong, Ping ^{[2
]}

Wang, Nai-Xing ^{[3
]}

机构：

[1] Hunan Normal Univ, Key Lab Chem Biol & Trad Chinese Med Res, Changsha 410081, Hunan, Peoples R China

[2] Wenzhou Univ, Coll Chem & Mat Sci, Wenzhou 325035, Peoples R China

[3] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100080, Peoples R China

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 09期

关键词：

D O I：

10.1021/ol8006315

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel palladium-catalyzed oxidative C-H functionalization protocol for the synthesis of (2-oxoindolin-3-ylidene)methyl acetates has been developed. In the presence of Pd(OAC)(2) and Phl(OAC)(2), a variety of N-arylpropiolamides underwent the C-H functionalization reaction with acids to afford the corresponding (E)-(2-oxoindolin-3-ylidene)methyl acetates selectively in moderate to excellent yields.

引用

页码：1875 / 1878

页数：4

共 41 条

[11] A novel one-pot synthesis of highly diverse indole scaffolds by the Ugi/Heck reaction [J].

Kalinski, Cedric ;

Umkehrer, Michael ;

Schmidt, Juergen ;

Ross, Guenther ;

Kolb, Juergen ;

Burdack, Christoph ;

Hiller, Wolfgang ;

Hoffmann, Stephan D. .

TETRAHEDRON LETTERS, 2006, 47 (27) :4683-4686

[12] A simple catalytic method for the regioselective halogenation of arenes [J].

Kalyani, Dipannita ;

Dick, Allison R. ;

Anani, Waseem Q. ;

Sanford, Melanie S. .

ORGANIC LETTERS, 2006, 8 (12) :2523-2526

[13] Molecular recognition of protein kinase binding pockets for design of potent and selective kinase inhibitors [J].

Liao, Jeffrey Jie-Lou .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (03) :409-424

[14] Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and SN2 C-O bond formation [J].

Liu, Guosheng ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7179-7181

[15] A NOVEL REGIO-SPECIFIC AND STEREO-SPECIFIC HYDROACETOXYLATION REACTION OF 2-ALKYNOIC ACID-DERIVATIVES [J].

LU, XY ;

ZHU, GX ;

MA, SM .

TETRAHEDRON LETTERS, 1992, 33 (47) :7205-7206

[16] Stereoselective synthesis 3-alkylideneoxindoles by rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryl- and alkenylboronic acids [J].

Miura, Tomoya ;

Takahashi, Yusuke ;

Murakami, Masahiro .

ORGANIC LETTERS, 2007, 9 (24) :5075-5077

[17] Structures of the tyrosine kinase domain of fibroblast growth factor receptor in complex with inhibitors [J].

Mohammadi, M ;

McMahon, G ;

Sun, L ;

Tang, C ;

Hirth, P ;

Yeh, BK ;

Hubbard, SR ;

Schlessinger, J .

SCIENCE, 1997, 276 (5314) :955-960

[18]

MORI M, 1979, TETRAHEDRON LETT, P1133

[19] Oxidative diamination of alkenes with ureas as nitrogen sources:: Mechanistic pathways in the presence of a high oxidation state palladium catalyst [J].

Muniz, Kilian ;

Hovelmann, Claas H. ;

Streuff, Jan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :763-773

[20] Advancing palladium-catalyzed C-N bond formation:: Bisindoline construction from successive amide transfer to internal alkenes [J].

Muniz, Kilian .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) :14542-+

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