Improvements in 1,3-dipolar cycloaddition of nitrones to fluorinated dipolarophiles under solvent-free microwave activation

被引：30
作者：
Loupy, A [1 ]
Petit, A [1 ]
BonnetDelpon, D [1 ]
机构：
[1] CTR ETUD PHARMACEUT,BIOCIS,SYNTH ORGAN LAB,CNRS,F-92296 CHATENAY MALABRY,FRANCE
来源：
JOURNAL OF FLUORINE CHEMISTRY | 1995年 / 75卷 / 02期
关键词：
dipolar cycloaddition; nitrones; fluorinated dipolarophiles; microwave activation; solvent-free conditions;
D O I：
10.1016/0022-1139(95)03330-6
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
1,3-Dipolar cycloadditions between ethyl trifluoracetoacetate or alpha-trifluoromethylstyrene and N-(benzylidene) methylamine N-oxide were performed in the absence of solvent. Under microwave irradiation in a monomode Maxidigest Prolabo reactor, quantitative yields were obtained within 3 min. Compared to conventional heating under the same conditions, the yields are significantly increased (from 55%-64% to 88.98%). Classical conditions using boiling toluene (65% within 24-48 h) are now considerably improved.
引用
收藏
页码：215 / 216
页数：2
相关论文
共 50 条
  • [41] Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts
    Kidou, Chihiro
    Mizoguchi, Haruki
    Nehira, Tatsuo
    Sakakura, Akira
    SYNLETT, 2019, 30 (15) : 1835 - 1839
  • [42] Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines
    Karcev, Dmitriy D.
    Efremova, Mariia M.
    Molchanov, Alexander P.
    Rostovskii, Nikolai, V
    Kryukova, Mariya A.
    Bunev, Alexander S.
    Khochenkov, Dmitry A.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2022, 23 (20)
  • [43] 1,3-Dipolar cycloaddition of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones and nitrile oxides: An experimental and theoretical investigation
    Efremova, Mariia M.
    Molchanov, Alexander P.
    Novikov, Alexander S.
    Starova, Galina L.
    Muryleva, Anna A.
    Slita, Alexander, V
    Zarubaev, Vladimir V.
    TETRAHEDRON, 2020, 76 (15)
  • [44] Synthesis and characterization of 5-substituted novel isoxazolidines derived from 1,3-dipolar cycloaddition of nitrones with olefins: Studies of antibacterial and antifungal activities
    Kumar, KRR
    Mallesha, H
    Rangappa, KS
    SYNTHETIC COMMUNICATIONS, 2003, 33 (09) : 1545 - 1555
  • [45] Microwave accelerated 1,3-dipolar cycloaddition reactions of cyclopentylidene N-phenyl nitrone with substituted N-arylmaleimides
    Singh, Manjit
    Singh, Baldev
    Singal, Kewal Krishan
    ASIAN JOURNAL OF CHEMISTRY, 2008, 20 (01) : 736 - 740
  • [46] 1,3-Dipolar cycloaddition of nitrones to transition metal-bound isocyanides: DFT and HSAB principle theoretical model together with analysis of vibrational spectra
    Novikov, Alexander S.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 797 : 8 - 12
  • [47] In situ mechanochemical synthesis of nitrones followed by 1,3-dipolar cycloaddition: a catalyst-free, "green" route to cis-fused chromano[4,3-c]isoxazoles
    Bhutia, Zigmee T.
    Geethika, P.
    Malik, Anurag
    Kumar, Vikash
    Chatterjee, Amrita
    Roy, Biswajit Gopal
    Banerjee, Mainak
    RSC ADVANCES, 2015, 5 (120): : 99566 - 99572
  • [48] Regio- and Stereoselective Synthesis of a Library of Bioactive Dispiro-Oxindolo/Acenaphthoquino Andrographolides via 1,3-Dipolar Cycloaddition Reaction Under Microwave Irradiation
    Hazra, Abhijit
    Bharitkar, Yogesh P.
    Chakraborty, Debanjana
    Mondal, Susanta Kumar
    Singal, Nupur
    Mondal, Shyamal
    Maity, Arindam
    Paira, Rupankar
    Banerjee, Sukdeb
    Mondal, Nirup B.
    ACS COMBINATORIAL SCIENCE, 2013, 15 (01) : 41 - 48
  • [49] A DFT Study of Mechanism, Diastereoselectivity, and Solvent Effects on the 1,3-Dipolar Cycloaddition Reaction between N-Methyltrichloromethylnitrone and Maleimide Derivatives
    Tliba, S.
    Yahia, W.
    Adjeroud, Y.
    Seddiki, K.
    Liacha, M.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2024, 94 (06) : 1375 - 1384
  • [50] Synthesis of Carbohydrate Mimetics by Intramolecular 1,3-Dipolar Cycloaddition of N-(3-Alkenyl)nitrones Derived from Unprotected d-Aldopentoses
    Malinowski, Maciej
    Rowicki, Tomasz
    Guzik, Patrycja
    Wielechowska, Monika
    Sas, Wojciech
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (06) : 763 - 771
12345