TBHP/I2-promoted oxidative coupling of acetophenones with amines at room temperature under metal-free and solvent-free conditions for the synthesis of α-ketoamides

被引：175

作者：

Zhang, Xiaobin ^{[1
]}

Wang, Lei ^{[1
,2
]}

机构：

[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

GREEN CHEMISTRY | 2012年 / 14卷 / 08期

基金：

美国国家科学基金会;

关键词：

ONE-POT SYNTHESIS; C-H ACTIVATION; DOUBLE CARBONYLATION; ARYL IODIDES; KETO AMIDE; INTRAMOLECULAR CYCLIZATION; CYCLOTHEONAMIDE-B; INHIBITORS; DERIVATIVES; IODINE;

D O I：

10.1039/c2gc35489f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel and efficient TBHP/I-2-promoted oxidative coupling reaction of acetophenones with amines for the synthesis of alpha-ketoamides has been developed. The reactions proceeded smoothly at room temperature under metal-free and solvent-free conditions and generated the corresponding products in good yields.

引用

页码：2141 / 2145

页数：5

共 57 条

[1] Synthesis of α-Keto-Imides via Oxidation of Ynamides [J].

Al-Rashid, Ziyad F. ;

Johnson, Whitney L. ;

Hsung, Richard P. ;

Wei, Yonggang ;

Yao, Pei-Yuan ;

Liu, Renhei ;

Zhao, Kang .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8780-8784

[2] A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline [J].

Boess, Esther ;

Schmitz, Corinna ;

Klussmann, Martin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5317-5325

[3] Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α-Ketoamides [J].

Bouma, Marinus ;

Masson, Geraldine ;

Zhu, Jieping .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08) :2748-2751

[4] Regiochemical observations on the lithiation of 1,2,4-trichlorobenzene and reaction with DMF and oxamide electrophiles in THF [J].

Burton, AJ ;

Cardwell, KS ;

Fuchter, MJ ;

Lindvall, MK ;

Patel, R ;

Packham, TW ;

Prodger, JC ;

Schilling, MB ;

Walker, MD .

TETRAHEDRON LETTERS, 2003, 44 (30) :5653-5656

[5] Pd-Catalyzed Ortho-C HAcylation/Cross Coupling of Aryl Ketone O-Methyl Oximes with Aldehydes Using tert-Butyl Hydroperoxide as Oxidant [J].

Chan, Chun-Wo ;

Zhou, Zhongyuan ;

Chan, Albert S. C. ;

Yu, Wing-Yiu .

ORGANIC LETTERS, 2010, 12 (17) :3926-3929

[6] P2-achiral, P'-extended α-ketoamide inhibitors of calpain I [J].

Chatterjee, S ;

Dunn, D ;

Tao, M ;

Wells, G ;

Gu, ZQ ;

Bihovsky, R ;

Ator, MA ;

Siman, R ;

Mallamo, JP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) :2371-2374

[7] A highly efficient TBAF-promoted intramolecular cyclization of gem-dibromoolefins for the synthesis of 2-bromobenzofurans(thiophenes) [J].

Chen, Wei ;

Zhang, Yicheng ;

Zhang, Lei ;

Wang, Min ;

Wang, Lei .

CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10476-10478

[8] 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

[9] Synthesis and study of a lipophilic α-keto amide inhibitor of pancreatic lipase [J].

Chiou, A ;

Markidis, T ;

Constantinou-Kokotou, V ;

Verger, R ;

Kokotos, G .

ORGANIC LETTERS, 2000, 2 (03) :347-350

[10] Copper-catalyzed direct oxidative synthesis of α-ketoamides from aryl methyl ketones, amines, and molecular oxygen [J].

Du, Feng-Tian ;

Ji, Jian-Xin .

CHEMICAL SCIENCE, 2012, 3 (02) :460-465

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