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
  • [41] Polyfunctional imidazoles: XII.1 Synthesis of 1-[(4-chloro-1H-imidazol-5-yl)methyl]-substituted 1,2,3-triazoles and dihydropyrrolo[3,4-d]triazoles from 5-(azidomethyl)-4-chloro-1H-imidazoles
    Grozav, A. N.
    Chornous, V. A.
    Vovk, M. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (06) : 873 - 878
  • [42] Synthesis and antitumor properties of some new N-(5-R-benzyl-1,3-thiazol-2-yl)-4,5-dihydro-1H-imidazole-2-carboxamides
    Horishny, Volodymyr Ya
    Drapak, Iryna, V
    Chaban, Taras, I
    Ostapiuk, Yuriy, V
    Matiychuk, Vasyl S.
    INDONESIAN JOURNAL OF PHARMACY, 2020, 31 (03): : 150 - 160
  • [43] Synthesis of 3-[5-(biphenyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn-1-ones by palladium-free cross-coupling between pyrroles and haloalkynes on aluminum oxide
    Sobenina, L. N.
    Stepanova, Z. V.
    Petrova, O. V.
    Ma, J. Sh
    Yang, G.
    Tatarinova, A. A.
    Mikhaleva, A. I.
    Trofimov, B. A.
    RUSSIAN CHEMICAL BULLETIN, 2013, 62 (01) : 88 - 92
  • [44] Synthesis and cytotoxic activity evaluation of some novel 1-(3-(aryl-4,5-dihydroisoxazol-5-yl)methyl)-4-trihalomethyl-1H-pyrimidin-2-ones in human cancer cells
    Lobo, Marcio M.
    Viau, Cassiana M.
    dos Santos, Josiane M.
    Bonacorso, Helio G.
    Martins, Marcos A. P.
    Amaral, Simone S.
    Saffi, Jenifer
    Zanatta, Nilo
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 101 : 836 - 842
  • [45] Synthesis, crystal structures and xanthine oxidase inhibitory activity of 2-(benzylthio)-5-[1-(4-fluorobenzyl)-3-phenyl-1H-pyrazol-5-yl]-1,3,4-oxadiazoles derivatives
    Qi, Deqiang
    You, Jinzong
    Wang, Xuejie
    Zhang, Yiping
    JOURNAL OF CHEMICAL RESEARCH, 2015, (12) : 706 - 710
  • [46] A Fragment-Derived Clinical Candidate for Antagonism of X-Linked and Cellular Inhibitor of Apoptosis Proteins: 1-(6-[(4-Fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl)-2-[(2R,5R)-5-methyl-2-([(3R)-3-methylmorpholin-4-yl]methyl)piperazin-1-yl]ethan-1-one (ASTX660)
    Johnson, Christopher N.
    Ahn, Jong Sook
    Buck, Ildiko M.
    Chiarparin, Elisabetta
    Day, James E. H.
    Hopkins, Anna
    Howard, Steven
    Lewis, Edward J.
    Martins, Vanessa
    Millemaggi, Alessia
    Munck, Joanne M.
    Page, Lee W.
    Peakman, Torren
    Reader, Michael
    Rich, Sharna J.
    Saxty, Gordon
    Smyth, Tomoko
    Thompson, Neil T.
    Ward, George A.
    Williams, Pamela A.
    Wilsher, Nicola E.
    Chessari, Gianni
    JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (16) : 7314 - 7329
  • [47] Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
    Chen, Hai-Lin
    Huang, Xiu-Xiang
    Yao, Dong-Mei
    Wang, Yan-Ping
    Lu, Xiao-Bing
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2021, 236 (06): : 1371 - 1373
  • [48] Synthesis, antimicrobial activity and DFT studies of 4,5-dihydro-9-methoxy-4-(5-methylisoxazol-3-yl)benzo[f][1,4]oxazepin-3(2H)-one
    Ramesh, Gaddam
    Kakkerla, Ramu
    Marri, Srinivas
    Haripriya, R.
    Reddy, Byru Venkatram
    MATERIALS TODAY-PROCEEDINGS, 2022, 50 : 340 - 347
  • [49] Pharmacological Characterization of 3-[3-tert-Butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionicAcid (AM103), a Novel Selective 5-Lipoxygenase-Activating Protein Inhibitor That Reduces Acute and Chronic Inflammation
    Lorrain, Daniel S.
    Bain, Gretchen
    Correa, Lucia D.
    Chapman, Charles
    Broadhead, Alex R.
    Santini, Angelina M.
    Prodanovich, Pat
    Darlington, Janice V.
    Hutchinson, John H.
    King, Christopher
    Lee, Catherine
    Baccei, Christopher
    Li, Yiwei
    Arruda, Jeannie M.
    Evans, Jilly F.
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2009, 331 (03): : 1042 - 1050
  • [50] Design, Synthesis, and Biological Evaluation of 3-(Imidazo[1,2-a]pyrazin-3-ylethynyl)-4-isopropyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide as a Dual Inhibitor of Discoidin Domain Receptors 1 and 2
    Wang, Zhen
    Zhang, Yali
    Pinkas, Daniel M.
    Fox, Alice E.
    Luo, Jinfeng
    Huang, Huocong
    Cui, Shengyang
    Xiang, Qiuping
    Xu, Tingting
    Xun, Qiuju
    Zhu, Dongsheng
    Tu, Zhengchao
    Ren, Xiaomei
    Brekken, Rolf A.
    Bullock, Alex N.
    Liang, Guang
    Ding, Ke
    Lu, Xiaoyun
    JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (17) : 7977 - 7990
12345