Synthesis of isoxazolyl substituted 1,2,4-oxadiazolines and pyrazolines

被引:0
|
作者
Geng, L [1 ]
Lei, M [1 ]
Wang, YG [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
1,3-dipolar cycloaddition; nitrile oxide; 1,2,4-oxadiazoline; pyrazoline;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile method for preparation of 5-methyl-5-[5-(tert-butyldimethylsiloxymethyl)-3-isoxazolyl]-3-aryl-4-(4-methyloxyphenyl)-4,5-dihydro-1,2,4-oxadiazoles (4a similar to 4e) via 1,3-dipolar cycloaddition of Schiff bases derived from 3-acetyl-5-hydroxymethylisoxazoles and nitrile oxides in situ generated from oximes was described. 5-(tert-Butyldimethylsiloxymethyl)-3-(1,5-diaryl-4,5-dihydropyrazol-3-yl)isoxazoles (6a similar to 6i) were also prepared through cycloaddition of aryl hydrazine and alpha,beta-unsaturated ketones (5) derived from 3-acetyl-5-hydroxylmethylisoxazoles. The structures of all new compounds were characterized by H-1 NMR, C-13 NMR, MS, IR and HRMS spectra.
引用
收藏
页码:690 / 695
页数:6
相关论文
共 30 条
  • [1] ANKHIWALA MD, 1990, J INDIAN CHEM SOC, V67, P514
  • [2] Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands
    Arai, MA
    Arai, T
    Sasai, H
    [J]. ORGANIC LETTERS, 1999, 1 (11) : 1795 - 1797
  • [3] Stereo- and chemoselectivity in 1,3-dipolar cycloaddition reaction of 2-diazopropane with diarylidenacetones
    Boukamcha, N
    Gharbi, R
    Martin, MT
    Chiaroni, A
    Mighri, Z
    Khemiss, A
    [J]. TETRAHEDRON, 1999, 55 (02) : 449 - 460
  • [4] A novel method for the generation of nitrile oxides on solid phase: Application to the synthesis of substituted benzopyranoisoxazoles
    Chao, EY
    Minick, DJ
    Sternbach, DD
    Shearer, BG
    Collins, JL
    [J]. ORGANIC LETTERS, 2002, 4 (03) : 323 - 326
  • [5] CHIMIRRI A, 1980, CHEM PHARM BULL, V28, P3296
  • [6] STEREOSPECIFIC CYCLOPROPENIC SYNTHESIS OF CIS-CHRYSANTHEMIC METHYL-ESTER .2. THE BY-PASSING DIAZOALKANE WAY
    FRANCKNEUMANN, M
    MIESCH, M
    [J]. TETRAHEDRON LETTERS, 1982, 23 (13) : 1409 - 1412
  • [7] HIROYUKI K, 2002, HETEROCYCLES, V57, P2299
  • [8] Regioselective synthesis of 1,3,5-triaryl-4-alkylpyrazoles: Novel ligands for the estrogen receptor
    Huang, YR
    Katzenellenbogen, JA
    [J]. ORGANIC LETTERS, 2000, 2 (18) : 2833 - 2836
  • [9] HENNOXAZOLES - BIOACTIVE BISOXAZOLES FROM A MARINE SPONGE
    ICHIBA, T
    YOSHIDA, WY
    SCHEUER, PJ
    HIGA, T
    GRAVALOS, DG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) : 3173 - 3174
  • [10] A novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives using ammonium cerium nitrate (CAN)
    Itoh, K
    Takahashi, S
    Ueki, T
    Sugiyama, T
    Takahashi, TT
    Horiuchi, CA
    [J]. TETRAHEDRON LETTERS, 2002, 43 (39) : 7035 - 7037