A method for generating nitrile oxides from nitroalkanes: a microwave assisted route for isoxazoles

被引：46

作者：

Giacomelli, G ^{[1
]}

De Luca, L ^{[1
]}

Porcheddu, A ^{[1
]}

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

TETRAHEDRON | 2003年 / 59卷 / 29期

关键词：

isoxazoline; solid-phase synthesis; microwave condition; ALPHA-AMINO-ACIDS; EFFICIENT; ALDOXIMES; CHLORIDE; ALCOHOLS; ESTERS;

D O I：

10.1016/S0040-4020(03)00859-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient route has been developed for generation of nitrile oxides in situ from nitroalkanes under very mild conditions using microwave irradiation, using 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) and DMAP as catalyst. Isoxazolines and isoxazoles are obtained in very good yields compared to known methods. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：5437 / 5440

页数：4

共 24 条

[1]

Basel Y, 1997, SYNTHESIS-STUTTGART, P309

[2]

Bunnelle WH, 1997, SYNTHESIS-STUTTGART, P439

[3] An efficient route to alkyl chlorides from alcohols using the complex TCT/DMF [J].

De Luca, L ;

Giacomelli, G ;

Porcheddu, A .

ORGANIC LETTERS, 2002, 4 (04) :553-555

[4] A mild and efficient alternative to the classical swern oxidation [J].

De Luca, L ;

Giacomelli, G ;

Porcheddu, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7907-7909

[5]

De Luca L, 2000, SYNTHESIS-STUTTGART, P1295

[6] Solid-phase synthesis of isoxazole-based amino acids: A new scaffold for molecular diversity [J].

De Luca, L ;

Giacomelli, G ;

Riu, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6823-6825

[7]

DOLE JA, 1973, J AM CHEM SOC, V95, P512

[8]

Falorni M, 2000, EUR J ORG CHEM, V2000, P3217

[9] Synthesis of new α-amino-acids containing the isoxazole moiety [J].

Falorni, M ;

Giacomelli, G ;

Spanu, E .

TETRAHEDRON LETTERS, 1998, 39 (50) :9241-9244

[10] NITRILE OXIDES .V. STABLE AROMATIC NITRILE OXIDES [J].

GRUNDMANN, C ;

DEAN, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (08) :2809-+

← 1 2 3 →