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] A convenient synthesis of 5-trichloromethyl-5-hydroxy-3-heteroalkyl-4,5-dihydroisoxazoles
    Martins, MAP
    Sinhorin, AP
    Zimmermann, NEK
    Zanatta, N
    Bonacorso, HG
    Bastos, GP
    SYNTHESIS-STUTTGART, 2001, (13): : 1959 - 1964
  • [2] A convenient synthesis of 5-trichloromethyl-5-hydroxy-3-heteroalkyl-4,5-dihydroisoxazoles
    Martins, M.A.P.
    Sinhorin, A.P.
    Zimmermann, N.E.K.
    Zanatta, N.
    Bonacorso, H.G.
    Bastos, G.P.
    Synthesis, 2001, (13) : 1959 - 1964
  • [3] Synthesis in Water and Antimicrobial Activity of 5-Trichloromethyl-4,5-dihydroisoxazoles
    Flores, Alex F. C.
    Piovesan, Luciana A.
    Souto, Alynne A.
    Pereira, Mariano A.
    Martins, Marcos A. P.
    Balliano, Tatiane L.
    da Silva, Givanildo S.
    SYNTHETIC COMMUNICATIONS, 2013, 43 (17) : 2326 - 2336
  • [4] Structural investigations of 5-hydroxy-4,5-dihydroisoxazoles
    Campos, Patrick T.
    Machado, Pablo
    Frizzo, Clarissa P.
    Moreira, Dayse N.
    Meyer, Alexandre R.
    Bonacorso, Helio G.
    Zanatta, Nilo
    Ducati, Lucas C.
    Rittner, Roberto
    Tormena, Claudio F.
    Martins, Marcos A. P.
    JOURNAL OF MOLECULAR STRUCTURE, 2011, 1006 (1-3) : 462 - 468
  • [5] SYNTHESIS AND REACTIVITY OF 5-AMINO-4,5-DIHYDROISOXAZOLES
    BARLUENGA, J
    JARDON, J
    GOTOR, V
    JOURNAL OF CHEMICAL RESEARCH, 1986, (12) : 464 - 464
  • [6] 5-Bromomethyl-4,5-dihydroisoxazoles
    Mosher, Michael D.
    Norman, Amber L.
    Shurrush, Khriesto A.
    TETRAHEDRON LETTERS, 2009, 50 (40) : 5647 - 5648
  • [7] Facile Regioselective Synthesis of 5-Hydroxy-4,5-dihydroisoxazoles from Acetylenic Ketones
    Xie, Meihua
    Li, Ming
    Liu, Changqing
    Zhang, Jitan
    Feng, Chengyou
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (06) : 1462 - 1465
  • [8] Synthesis of 3-aryl-5-diethoxyphosphorylethyne-4,5-dihydroisoxazoles
    V. K. Brel’
    Chemistry of Heterocyclic Compounds, 2012, 48 : 907 - 911
  • [9] Synthesis of 3-aryl-5-diethoxyphosphorylethyne-4,5-dihydroisoxazoles
    Brel, V. K.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (06) : 907 - 911
  • [10] Ultrasound promoted synthesis of 5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles and β-enamino trihalomethyl ketones in water
    Martins, MAP
    Pereira, CMP
    Cunico, W
    Moura, S
    Rosa, FA
    Peres, RL
    Machado, P
    Zanatta, N
    Bonacorso, HG
    ULTRASONICS SONOCHEMISTRY, 2006, 13 (04) : 364 - 370