Facile synthesis of 3-aryl-5-(2-oxopyrrolidin-1-yl)- and 5-(pyridin-4-yl)-4,5-dihydroisoxazoles via 1,3-dipolar cycloaddition under mild conditions

被引：15
|
作者：
Gong, Yan [1 ]
Wang, Yong [1 ]
Zhao, Wen-Tao [1 ]
Tang, Xiang-Yang [1 ]
机构：
[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
来源：
JOURNAL OF CHEMICAL RESEARCH | 2013年 / 08期
基金：
中国国家自然科学基金;
关键词：
1,3-dipolarcycloaddition; 3-aryl-5-(2-oxopyrrolidin-1-yl)-4,5-dihydroisoxazoles; 3-aryl-5-(pyridin-4-yl)-4,5-dihydroisoxazoles; nitrile oxides; POTENT; DISCOVERY;
D O I：
10.3184/174751913X13735527483211
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A convenient and efficient synthetic approach for the synthesis of 5-substituted 3-aryl-4,5-dihydroisoxazoles is reported. In the presence of triethylamine, a series of hydroximoyl chlorides were transformed into nitrile oxides, followed by reaction with N-vinyl-2-pyrrolidinone (or 4-vinylpyridine) by a 1,3-dipolar cycloaddition to give novel 4,5-dihydroisoxazole derivatives.
引用
收藏
页码：499 / 502
页数：4
相关论文
共 50 条
  • [1] [5-(1,3-Diphenyl-1H-pyrazol-4-yl)-3-phenyl-4,5-dihydropyrazol-1-yl](pyridin-4-yl)methanone
    Kaushik, Darpan
    Nagpal, Upasana
    Verma, Tarawanti
    Madan, Kapish
    MOLBANK, 2011, (01)
  • [2] 4-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]pyridinium benzoate
    Han, Meng Ting
    Zhang, Yuan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O447 - U1343
  • [3] Ethyl 2-[5-(4-fluorophenyl)pyridin-3-yl]1-[3-(2-oxopyrrolidin-1-yl) propyl]-1H-benzimidazole-5-carboxylate
    Yeong, Keng Yoon
    Ali, Mohamed Ashraf
    Choon, Tan Soo
    Rosli, Mohd Mustaqim
    Razak, Ibrahim Abdul
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1013 - +
  • [4] Synthesis of 5-(thiazol-5-yl)-4,5-dihydroisoxazoles from 3-chloropentane-2,4-dione
    Milinkevich, Kristin A.
    Ye, Long
    Kurth, Mark J.
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (04): : 521 - 525
  • [5] Synthesis, antibacterial and antifungal activities of 3-aryl-5-(pyridin-3-yl)-4,5-dihydropyrazole-1-carbothioamide derivatives
    M. Shekarchi
    M. Pirali-Hamedani
    L. Navidpour
    N. Adib
    A. Shafiee
    Journal of the Iranian Chemical Society, 2008, 5 : 150 - 158
  • [6] 1,3-dipolar cycloaddition of nitrile oxides to 1-phenylsulfonyl-1,3-butadienes: synthesis of 3-(4,5-dihydroisoxazol-5-yl)pyrroles
    Hwang, SH
    Kurth, MJ
    TETRAHEDRON LETTERS, 2002, 43 (01) : 53 - 56
  • [7] Facile Synthesis of Isoniazid Derivatives-1-[2-(3-Aryl(Hetaryl)-1-Phenyl-1H-Pyrazol-4-yl)-5-(Pyridin-4-yl)-1,3,4-Oxadiazol-3(2H)-yl]Ethanones
    Chaudhry, Faryal
    Munawar, Munawar Ali
    Khan, Misbahul Ain
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (05) : 615 - 618
  • [8] Facile Synthesis of Isoniazid Derivatives – 1-[2-(3-Aryl(Hetaryl)-1-Phenyl-1H-Pyrazol-4-yl)-5-(Pyridin-4-yl)-1,3,4-Oxadiazol-3(2H)-yl]Ethanones
    Faryal Chaudhry
    Munawar Ali Munawar
    Misbahul Ain Khan
    Chemistry of Heterocyclic Compounds, 2020, 56 : 615 - 618
  • [9] 1,4-Bis{[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}butane
    Liu, Qing-lei
    Wang, Wei
    Gao, Yan
    Jia, Xiao-yu
    Zhang, Jing-jing
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O740 - U2858
  • [10] Synthesis and Antibacterial Evaluation of Some Novel 1-(5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-3-chloro-4-aryl-azetidin-2-one Derivatives
    Alsaiari, Ahad Amer
    Almehmadi, Mazen Mohammed
    Asif, Mohammad
    LATIN AMERICAN JOURNAL OF PHARMACY, 2023, 42 (02): : 339 - 343
12345