Molecular Iodine-Mediated Domino Reaction for the Synthesis of Benzamides, 2,2-Diazidobenzofuran-3(2H)-ones and Benzoxazolones

被引：27

作者：

Rajendar, K. ^{[1
]}

Kant, Ruchir ^{[2
]}

Narender, T. ^{[1
]}

机构：

[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, Uttar Pradesh, India

[2] CSIR Cent Drug Res Inst, Mol & Struct Biol Div, Lucknow 226051, Uttar Pradesh, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 18期

关键词：

benzamides; benzoxazolones; Curtius rearrangement; 2; 2-diazidobenzofuran-3(2H)-ones; Haller-Bauer reaction; iodine; sodium azide; PRIMARY AMIDES; ONE-POT; OXIDATIVE CYCLOCARBONYLATION; CATALYZED HYDRATION; BETA-AMINOALCOHOLS; CARBOXYLIC-ACIDS; PRIMARY AMINES; EFFICIENT; ALDOXIMES; ALDEHYDES;

D O I：

10.1002/adsc.201300668

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A simple and efficient domino protocol has been developed for the preparation of biologically important benzamides, 2,2-diazidobenzofuran-3(2H)-ones and benzoxazolones from various structurally and electronically divergent acetophenones and ortho-hydroxyacetophenones in the presence of molecular iodine, sodium azide and sodium bicarbonate at 100 degrees C in good to excellent yields.

引用

页码：3591 / 3596

页数：6

共 61 条

[1] Novel Synthesis of Primary Arylamides from Aryl Methyl Ketone Oxidations using Iodine in Aqueous Ammonia [J].

Angeles, Norma A. ;

Villavicencio, Felipe ;

Guadarrama, Carlos ;

Corona, David ;

Cuevas-Yanez, Erick .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (05) :905-908

[2]

[Anonymous], 1870, JUSTUS LIEBIGS ANN S

[3]

[Anonymous], 2008, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.200802464

[4]

[Anonymous], Japanese Patent, Patent No. [JP 82102876, 82102876]

[5]

[Anonymous], Japanese Patent, Patent No. [JP 83225072, 83225072]

[6]

Beckwith A.L.J., 1970, CHEM AMIDES, P73

[7] Non-catalytic clean synthesis route using urea to cyclic urea and cyclic urethane compounds [J].

Bhanage, BM ;

Fujita, S ;

Ikushima, Y ;

Arai, M .

GREEN CHEMISTRY, 2004, 6 (02) :78-80

[8]

Bode J.W., 2006, ANGEW CHEM, V118, P1270, DOI DOI 10.1021/JA204277B

[9] 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

[10] Large-scale manufacture of peptide therapeutics by chemical synthesis [J].

Bray, BL .

NATURE REVIEWS DRUG DISCOVERY, 2003, 2 (07) :587-593

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