Metal free one-pot synthesis of α-ketoamides from terminal alkenes

被引：45

作者：

Dutta, Sayan ^{[1
]}

Kotha, Surya Srinivas ^{[1
]}

Sekar, Govindasamy ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

RSC ADVANCES | 2015年 / 5卷 / 58期

关键词：

OXIDATIVE SYNTHESIS; METHYL KETONES; BETA-DIKETONES; BOND FORMATION; AMINES; ACCESS; INHIBITORS; ACETOPHENONES; AMIDATION; STRATEGY;

D O I：

10.1039/c5ra05671c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical approach towards the synthesis of alpha-ketoamides from readily available terminal alkenes (styrenes) has been developed. Use of inexpensive I-2/2-iodoxybenzoic acid (IBX) in dimethyl sulphoxide (DMSO) as an oxidant under metal free one-pot conditions makes this methodology versatile.

引用

页码：47265 / 47269

页数：5

共 48 条

[1] High-Yielding Oxidation of β-Hydroxyketones to β-Diketones Using o-Iodoxybenzoic Acid [J].

Bartlett, Samuel L. ;

Beaudry, Christopher M. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) :9852-9855

[2] o-Iodoxybenzoic acid- and tetraethylammonium bromide-mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles [J].

Bhalerao, Dinesh S. ;

Mahajan, Ulhas S. ;

Chaudhari, Kiran H. ;

Akamanchi, Krishnacharya G. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :662-665

[3] HIV-1 protease: mechanism and drug discovery [J].

Brik, A ;

Wong, CH .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (01) :5-14

[4] Synthesis of α-ketoamides from a carbamoylsilane and acid chlorides [J].

Chen, JX ;

Cunico, RF .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5509-5511

[5] Iodine-Promoted Oxidative Amidation of Terminal Alkenes - Synthesis of α-Ketoamides, Benzothiazoles, and Quinazolines [J].

Deshidi, Ramesh ;

Devari, Shekaraiah ;

Shah, Bhahwal Ali .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (07) :1428-1432

[6] 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

[7] Study of the cis-trans isomerization of the amino-acyl prolyl peptide bond. Application to the design of novel inhibitors of immunophilins. [J].

Dugave, C .

CURRENT ORGANIC CHEMISTRY, 2002, 6 (15) :1397-1431

[8]

Etzkorn F., 2006, Patent No. [WO 2006124494A1, 2006124494]

[9] A user-friendly entry to 2-iodoxybenzoic acid (IBX) [J].

Frigerio, M ;

Santagostino, M ;

Sputore, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4537-4538

[10] BIOACTIVE MARINE METABOLITES .33. CYCLOTHEONAMIDES, POTENT THROMBIN INHIBITORS, FROM A MARINE SPONGE THEONELLA SP [J].

FUSETANI, N ;

MATSUNAGA, S ;

MATSUMOTO, H ;

TAKEBAYASHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7053-7054

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