Microwave assisted synthesis of 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazoles

被引:31
作者
Martins, MAP [1 ]
Beck, P [1 ]
Cunico, W [1 ]
Pereira, CMP [1 ]
Sinhorin, AP [1 ]
Blanco, RF [1 ]
Peres, R [1 ]
Bonacorso, HG [1 ]
Zanatta, N [1 ]
机构
[1] Univ Fed Santa Maria, Dept Quim, BR-105900 Santa Maria, RS, Brazil
关键词
microwave irradiations; isoxazoles; enones; halogen compounds;
D O I
10.1016/S0040-4039(02)01555-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 13 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazoles have been synthesized in 78-96% yield by environmentally benign microwave induced techniques involving the cyclocondensation of 4-alkoxy-1,1,1-trichloro-3-alken-2-ones [CCl3C(O)C(R-2)=C(R-1)OR, where R-2=H, alkyl; R-1=H, alkyl, aryl and R=H, alkyl] with hydroxylamine using toluene as solvent. The advantages obtained by the use of microwave irradiation in relation to a classical method were demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7005 / 7008
页数:4
相关论文
共 50 条
[1]   Synthesis and structure-activity relationship of a new series of potent AT(1) selective angiotensin II receptor antagonists: 5-(biphenyl-4-ylmethyl)pyrazoles [J].
Almansa, C ;
Gomez, LA ;
Cavalcanti, FL ;
deArriba, AF ;
GarciaRafanell, J ;
Forn, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (04) :547-558
[2]   Trifluoroacetylation of unsymmetrical ketone acetals. A convenient route to obtain alkyl side chain trifluoromethylated heterocycles [J].
Bonacorso, HG ;
Martins, MAP ;
Bittencourt, SRT ;
Lourega, RV ;
Zanatta, N ;
Flores, AFC .
JOURNAL OF FLUORINE CHEMISTRY, 1999, 99 (02) :177-182
[3]   Haloacetylated enol ethers:: 12 [18].: Regiospecific synthesis and structural determination of stable 5-hydroxy-1H-pyrazolines [J].
Bonacorso, HG ;
Oliveira, MR ;
Wentz, AP ;
Wastowski, AD ;
de Oliveira, AB ;
Höerner, M ;
Zanatta, N ;
Martins, MAP .
TETRAHEDRON, 1999, 55 (02) :345-352
[4]   A convenient method for the synthesis of 2-trichloromethyl-4-p-substituted-phenyl-3H-1,5-benzodiazepines. [J].
Bonacorso, HG ;
Bittencourt, ST ;
Wastowski, AD ;
Wentz, AP ;
Zanatta, N ;
Martins, MAP .
TETRAHEDRON LETTERS, 1996, 37 (51) :9155-9156
[5]   Haloacetylated enol ethers.: 13.: Synthesis of N-[1-aryl(alkyl)-3-oxo-4,4,4-trichloro-1-buten-1-yl]-o-phenylenediamines and 2-trichloromethyl-4-aryl-3H-1,5-benzodiazepines [J].
Bonacorso, HG ;
Bittencourt, SRT ;
Wastowski, AD ;
Wentz, AP ;
Zanatta, N ;
Martins, MAP .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (01) :45-48
[6]  
BONACORSO HG, 2000, SYNTHESIS-STUTTGART, P1
[7]   HALOACETYLATED ENOL ETHERS .2. SYNTHESIS OF 5-TRIFLUOROMETHYLPYRAZOLES [J].
BRAIBANTE, MEF ;
CLAR, G ;
MARTINS, MAP .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (04) :1159-1160
[8]  
BUNTAIN IG, 1990, Patent No. 295117
[9]  
COLLA A, 1991, SYNTHESIS-STUTTGART, P483
[10]   Microwave assisted one pot synthesis of a series of trifluoromethyl substituted spiro [indole-triazoles] [J].
Dandia, A ;
Singh, R ;
Sachdeva, H ;
Arya, K .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 111 (01) :61-67