Facile Synthesis of Pyrimidine-Isoxazoline Hybrids in a [bmim][PF6]-Water Biphasic System

被引：1

作者：

Lanjewar, Kushal ^{[1
]}

Rahatgaonkar, Anjali ^{[1
]}

Chorghade, Mukund ^{[2
]}

Saraf, Binda ^{[1
]}

机构：

[1] Inst Sci, Dept Chem, Nagpur 440001, Maharashtra, India

[2] Chorghade Enterprises, Natick, MA 01760 USA

来源：

SYNTHESIS-STUTTGART | 2011年 / 16期

关键词：

pyrimidines; dihydroisoxazoles; ionic liquids; water; biphasic systems; SOLID-PHASE SYNTHESIS; NITRILE OXIDES; HYDROXIMOYL CHLORIDES; 2-ISOXAZOLINES; ALDOXIMES; ROUTE;

D O I：

10.1055/s-0030-1260099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The convenient synthesis of a library of pyrimidine-isoxazoline hybrids in 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6])-water/potassium hydroxide at ambient temperature has been accomplished. The ionic liquid [bmim][PF6], immiscible in water, can be easily recycled for reuse after separation of the products without any noticeable diminution in its activity. The protocol is rapid, the yields are good to excellent, and the method is facile.

引用

页码：2644 / 2650

页数：7

共 30 条

[1] Examination of ionic liquids and their interaction with molecules, when used as stationary phases in gas chromatography [J].

Armstrong, DW ;

He, LF ;

Liu, YS .

ANALYTICAL CHEMISTRY, 1999, 71 (17) :3873-3876

[2] A NEW METHOD FOR STEREOSELECTIVE HOMOALLYLIC AMINE SYNTHESIS [J].

ARMSTRONG, SK ;

COLLINGTON, EW ;

KNIGHT, JG ;

NAYLOR, A ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13) :1433-1447

[3] 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

[4] Synthesis of some new steroidal [16α, 17α-d]-isoxazolines [J].

Chowdhury, P ;

Das, AM ;

Goswami, P .

STEROIDS, 2005, 70 (08) :494-498

[5] Design of novel conformationally restricted analogues of glutamic acid [J].

Conti, P ;

De Amici, M ;

Roda, G ;

Vistoli, G ;

Stensbol, TB ;

Bräuner-Osborne, H ;

Madsen, U ;

Toma, L ;

De Micheli, C .

TETRAHEDRON, 2003, 59 (09) :1443-1452

[6] 1,3-DIPOLAR ADDITION-REACTIONS OF 6-ETHYLIDENEOLIVANIC ACID-DERIVATIVES WITH DIAZOMETHANE AND ACETONITRILE OXIDE [J].

CORBETT, DF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (03) :421-428

[7] COMPETITION EXPERIMENTS FOR THE DETECTION OF ACYL NITRENES [J].

EIBLER, E ;

KASBAUER, J ;

POHL, H ;

SAUER, J .

TETRAHEDRON LETTERS, 1987, 28 (10) :1097-1100

[8] Synthesis of novel 3-[5-ethyl-2-(2-phenoxy-ethyl)pyridin]-5-substituted isoxazoline libraries via 1,3-dipolar cycloaddition and evaluation of antimicrobial activities [J].

Gaonkar, S. L. ;

Rai, K. M. Lokanatha ;

Prabhuswamy, B. .

MEDICINAL CHEMISTRY RESEARCH, 2007, 15 (7-8) :407-417

[9] Synthesis of dihydroisoxazole nucleoside and nucleotide analogs [J].

Gi, HJ ;

Xiang, YJ ;

Schinazi, RF ;

Zhao, K .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :88-92

[10] Solid-phase synthesis of liquid crystalline isoxazole library [J].

Haino, T ;

Tanaka, M ;

Ideta, K ;

Kubo, K ;

Mori, A ;

Fukazawa, Y .

TETRAHEDRON LETTERS, 2004, 45 (11) :2277-2279

← 1 2 3 →