NIS-Catalyzed Reactions: Amidation of Acetophenones and Oxidative Amination of Propiophenones

被引：151

作者：

Lamani, Manjunath ^{[1
]}

Prabhu, Kandikere Ramaiah ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 46期

关键词：

acetophenones; amination; dehydrogenation; N-iodosuccinimide; oxidation; propiophenones; DOUBLE CARBONYLATION; ALPHA-KETOAMIDES; EFFICIENT SYNTHESIS; ACID-DERIVATIVES; SINGLET OXYGEN; METAL-FREE; INHIBITORS; KETONES; AMIDES; TEMPERATURE;

D O I：

10.1002/chem.201202703

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Single-step amination: The N-iodosuccinimide (NIS)-catalyzed amidation of acetophenone derivatives by using tert-butylhydroperoxide (TBHP) as an oxidant is presented. A variety of acetyl derivatives of heterocyclic compounds were easily converted to their corresponding ketoamides under these conditions. A new, NIS-catalyzed amination of propiophenone and its derivatives in the presence of TBHP to furnish the corresponding 2-aminoketone derivatives is the first reported single-step amination of propiophenone derivatives. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：14638 / 14642

页数：5

共 50 条

[21]

Ling K.-Q, 1998, TETRAHEDRON LETT, V39, P2381

[22] On the reactions of 1,3-isoquinolinediones with singlet oxygen [J].

Ling, KQ ;

Ye, JH ;

Chen, XY ;

Ma, DJ ;

Xu, JH .

TETRAHEDRON, 1999, 55 (30) :9185-9204

[23] A General and Efficient Copper Catalyst for the Double Carbonylation Reaction [J].

Liu, Jianming ;

Zhang, Rongzhao ;

Wang, Shoufeng ;

Sun, Wei ;

Xia, Chungu .

ORGANIC LETTERS, 2009, 11 (06) :1321-1324

[24] Cross Coupling of Acyl and Aminyl Radicals: Direct Synthesis of Amides Catalyzed by Bu4NI with TBHP as an Oxidant [J].

Liu, Zhaojun ;

Zhang, Jie ;

Chen, Shulin ;

Shi, Erbo ;

Xu, Yuan ;

Wan, Xiaobing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (13) :3231-3235

[25] SYNTHETIC AND NATURALLY-OCCURRING PROTEASE INHIBITORS CONTAINING AN ELECTROPHILIC CARBONYL GROUP [J].

MEHDI, S .

BIOORGANIC CHEMISTRY, 1993, 21 (03) :249-259

[26] 1-(4-methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors [J].

Meltzer, PC ;

Butler, D ;

Deschamps, JR ;

Madras, BK .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (04) :1420-1432

[27] Accelerating reactions with microreactors at elevated temperatures and pressures: Profiling aminocarbonylation reactions [J].

Murphy, Edward R. ;

Martinelli, Joseph R. ;

Zaborenko, Nikolay ;

Buchwald, Stephen L. ;

Jensen, Klavs F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1734-1737

[28]

Murphy EdwardR., 2007, ANGEW CHEM INT EDIT, V119, P1764

[29] A new family of small molecules to probe the reactivation of mutant p53 [J].

Myers, MC ;

Wang, J ;

Iera, JA ;

Bang, JK ;

Hara, T ;

Saito, S ;

Zambetti, GP ;

Appella, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6152-6153

[30] A two-step, one-pot synthesis of diverse N-pyruvoyl amino acid derivatives using the Ugi reaction [J].

Nakamura, M ;

Inoue, J ;

Yamada, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (24) :2807-2810

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