Palladium-Catalyzed Serendipitous Synthesis of Arylglyoxylic Amides from Arylglyoxylates and N,N-Dialkylamides in the Presence of Halopyridines

被引：6

作者：

Laha, Joydev K. ^{[1
]}

Patel, Ketul V. ^{[1
]}

Tummalapalli, K. S. Satyanarayana ^{[1
]}

Hunjan, Mandeep Kaur ^{[1
]}

机构：

[1] Natl Inst Pharmaceut Educ & Res, Dept Pharmaceut Technol Proc Chem, Mohali 160062, Punjab, India

来源：

ACS OMEGA | 2018年 / 3卷 / 08期

关键词：

ALPHA-OXOCARBOXYLIC ACIDS; COUPLING REAGENTS; AEROBIC OXIDATION; PEPTIDE-SYNTHESIS; 2-PYRIDYL ESTERS; KETO ACIDS; C-H; KETOAMIDES; AMIDATION; AMINES;

D O I：

10.1021/acsomega.8b00894

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed synthesis of arylglyoxylic amides by the reaction of arylglyoxylates and N,N-dialkylamides in the presence of a 2,3-dihalopyridine has been realized for the first time. An anticipated 2,3 diaroylpyridine did not form in this reaction. The current study unveils an unprecedented role of 2,3-dihalopyridine toward this amidation. Our mechanistic study reveals that the arylglyoxylate could react with halopyridine to form a traceless activated pyridyl ester of arylglyoxylic acid, which upon subsequent reaction with amino surrogate, N,N-dialkylamides could form the arylglyoxylic amides.

引用

页码：8787 / 8793

页数：7

共 34 条

[1] Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids [J].

Bode, JW ;

Fox, RM ;

Baucom, KD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1248-1252

[2] Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors [J].

Chen, YH ;

Zhang, YH ;

Zhang, HJ ;

Liu, DZ ;

Gu, M ;

Li, JY ;

Wu, F ;

Zhu, XZ ;

Li, J ;

Nan, F .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (05) :1613-1623

[3] Direct Amidation of Aldoses and Decarboxylative Amidation of α-Keto Acids: An Efficient Conjugation Method for Unprotected Carbohydrate Molecules [J].

Cho, Chia-China ;

Liu, Jia-Nan ;

Chien, Chung-Hsun ;

Shie, Jiun-Jie ;

Chen, Ying-Chu ;

Fang, Jim-Min .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04) :1549-1556

[4] Development of Decarboxylative Coupling Processes for the Synthesis of Azomethines and Ketones [J].

Collet, Florence ;

Song, Bingrui ;

Rudolphi, Felix ;

Goossen, Lukas J. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (32) :6486-6501

[5] Nonclassical Routes for Amide Bond Formation [J].

de Figueiredo, Renata Marcia ;

Suppo, Jean-Simon ;

Campagne, Jean-Marc .

CHEMICAL REVIEWS, 2016, 116 (19) :12029-12122

[6] Recent Developments in General Methodologies for the Synthesis of α-Ketoamides [J].

De Risi, Carmela ;

Pollini, Gian Piero ;

Zanirato, Vinicio .

CHEMICAL REVIEWS, 2016, 116 (05) :3241-3305

[7] A general metal free approach to α-ketoamides via oxidative amidation-diketonization of terminal alkynes [J].

Deshidi, Ramesh ;

Kumar, Manjeet ;

Devari, Shekaraiah ;

Shah, Bhahwal Ali .

CHEMICAL COMMUNICATIONS, 2014, 50 (67) :9533-9535

[8] Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals [J].

Dunetz, Joshua R. ;

Magano, Javier ;

Weisenburger, Gerald A. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (02) :140-177

[9] POLYPEPTIDES .12. PREPARATION OF 2-PYRIDYL ESTERS AND THEIR USE IN PEPTIDE SYNTHESIS [J].

DUTTA, AS ;

MORLEY, JS .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (17) :2896-&

[10] TBAI-catalyzed synthesis of α-ketoamides via sp3 C-H radical/radical cross-coupling and domino aerobic oxidation [J].

Fan, Weizheng ;

Shi, Dongyang ;

Feng, Bainian .

TETRAHEDRON LETTERS, 2015, 56 (31) :4638-4641

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