Facile Synthesis of Disubstituted Isoxazoles from Homopropargylic Alcohol via C=N Bond Formation

被引：60

作者：

Gao, Pin ^{[1
]}

Li, Hong-Xia ^{[1
]}

Hao, Xin-Hua ^{[1
]}

Jin, Dong-Po ^{[1
]}

Chen, Dao-Qian ^{[1
]}

Yan, Xiao-Biao ^{[1
]}

Wu, Xin-Xing ^{[1
]}

Song, Xian-Rong ^{[1
]}

Liu, Xue-Yuan ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 24期

基金：

美国国家科学基金会;

关键词：

REGIOSPECIFIC SYNTHESIS; COPPER(I)-CATALYZED SYNTHESIS; NITRILE OXIDES; NITRATION; ACID; CYCLOADDITION; DECOMPOSITION; CONSTRUCTION; CONVERSION; ALKYNES;

D O I：

10.1021/ol503228x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C-N bond and C-O bond, CH oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.

引用

页码：6298 / 6301

页数：4

共 50 条

[1] One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling [J].

Ahmed, MSM ;

Kobayashi, K ;

Mori, A .

ORGANIC LETTERS, 2005, 7 (20) :4487-4489

[2] ON THE OXIMATION OF DIARYL-BETA-DIKETONES [J].

BANDIERA, T ;

GRUNANGER, P ;

ALBINI, FM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (06) :1423-1428

[3] USEFUL, REGIOSPECIFIC SYNTHESIS OF ISOXAZOLES [J].

BARBER, GN ;

OLOFSON, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :3015-3021

[4] Efficient synthesis of isoxazoles and isoxazolines from aldoximes using Magtrieve™ (CrO2) [J].

Bhosale, Sandeep ;

Kurhade, Santosh ;

Prasad, Uppuleti Viplava ;

Palle, Venkata P. ;

Bhuniya, Debnath .

TETRAHEDRON LETTERS, 2009, 50 (27) :3948-3951

[5] Cascade Formation of Isoxazoles: Facile Base-Mediated Rearrangement of Substituted Oxetanes [J].

Burkhard, Johannes A. ;

Tchitchanov, Boris H. ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (23) :5379-5382

[6] Effect of Aqueous Polyethylene Glycol on 1,3-Dipolar Cycloaddition of Benzoylnitromethane/Ethyl 2-Nitroacetate with Dipolarophiles: Green Synthesis of Isoxazoles and Isoxazolines [J].

Chary, R. Gangadhara ;

Reddy, G. Rajeshwar ;

Ganesh, Y. S. S. ;

Prasad, K. Vara ;

Raghunadh, Akula ;

Krishna, T. ;

Mukherjee, Soumita ;

Pal, Manojit .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (01) :160-164

[7] Dehydrogenative N-Incorporation: A Direct Approach to Quinoxaline N-Oxides under Mild Conditions [J].

Chen, Feng ;

Huang, Xiaoqiang ;

Li, Xinyao ;

Shen, Tao ;

Zou, Miancheng ;

Jiao, Ning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (39) :10495-10499

[8] Ethyl α-Nitrocinnamates in the Synthesis of Highly Functionalized Isoxazoles [J].

Chen, Kuang-Po ;

Chen, Yu-Jyun ;

Chuang, Che-Ping .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (27) :5292-5300

[9] A Regioselective Route to 5-Substituted Isoxazole- and Isoxazoline-3-phosphonates [J].

Conti, Paola ;

Pinto, Andrea ;

Tamborini, Lucia ;

Dunkel, Petra ;

Gambaro, Veniero ;

Visconti, Giacomo L. ;

De Micheli, Carlo .

SYNTHESIS-STUTTGART, 2009, (04) :591-596

[10] Regiospecific synthesis of 5-silyl azoles [J].

Cuadrado, P ;

González-Nogal, AM ;

Valero, R .

TETRAHEDRON, 2002, 58 (24) :4975-4980

← 1 2 3 4 5 →