Erlenmeyer azlactone synthesis with aliphatic aldehydes under solvent-free microwave conditions

被引:24
作者
Chandrasekhar, Sosale [1 ]
Karri, Phaneendrasai [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
aliphatic aldehydes; alumina; azlactones; Erlenmeyer synthesis; microwave; oxazolone; solvent-free;
D O I
10.1016/j.tetlet.2006.11.174
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Phenyl-5(4H)-oxazolone (azlactone) reacts with aliphatic aldehydes upon adsorption on neutral alumina and irradiation with microwaves (< 2 min). The corresponding condensation products are obtained in good yields (62-78%), indicating the satisfactory resolution of a long-standing problem plaguing the classical Erlenmeyer synthesis (poor results with aliphatic aldehydes). Plausible mechanistic reasons for the success of the procedure are discussed. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:785 / 786
页数:2
相关论文
共 50 条
  • [41] Microwave-assisted Michael addition of amides to α,β-unsaturated esters under solvent-free conditions
    Zare, A.
    Hasaninejad, A.
    Parhami, A.
    Zare, A. R. Moosavi
    Khalafi-Nezhad, A.
    POLISH JOURNAL OF CHEMISTRY, 2008, 82 (05) : 1059 - 1066
  • [42] Microwave-Assisted Condensation Reactions of Acetophenone Derivatives and Activated Methylene Compounds with Aldehydes Catalyzed by Boric Acid under Solvent-Free Conditions
    Brun, Elodie
    Safer, Abdelmounaim
    Carreaux, Francois
    Bourahla, Khadidja
    L'helgoua'ch, Jean-Martial
    Bazureau, Jean-Pierre
    Manuel Villalgordo, Jose
    MOLECULES, 2015, 20 (06) : 11617 - 11631
  • [43] Synthesis of Cycloveratrylene Macrocycles and Benzyl Oligomers Catalysed by Bentonite under Microwave/Infrared and Solvent-Free Conditions
    Miranda, Rene
    Valencia-Vazquez, Omar
    Abel Maya-Vega, Carlos
    Nicolas-Vazquez, Ines
    Marina Vargas-Rodriguez, Yolanda
    Antonio Morales-Serna, Jose
    Garcia-Rios, Erendira
    Salmon, Manuel
    MOLECULES, 2013, 18 (10): : 12820 - 12844
  • [44] Iodination of alcohols using triphenylphosphine/iodine under solvent-free conditions using microwave irradiation
    Hajipour, Abdol Reza
    Falahati, Ali Reza
    Ruoho, Arnold E.
    TETRAHEDRON LETTERS, 2006, 47 (25) : 4191 - 4196
  • [45] Uncatalyzed and solvent-free knoevenagel condensation under microwave irradiation or heating conditions
    Wang, GW
    Wang, BL
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (01) : 85 - 87
  • [46] One-pot preparation of fluorinated propargylamines under microwave irradiation and solvent-free conditions
    Du, Wei-Qiong
    Zhang, Jian-Min
    Wu, Ran
    Liang, Qin
    Zhu, Shi-Zheng
    JOURNAL OF FLUORINE CHEMISTRY, 2008, 129 (08) : 695 - 700
  • [47] Microwave accelerated solvent-free synthesis of flavanones
    Sagrera, GJ
    Seoane, GA
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2005, 16 (04) : 851 - 856
  • [48] Catalyst-free and solvent-free method for the synthesis of quinoxalines under microwave irradiation
    Zhou, Jian Feng
    Gong, Gui Xia
    Shi, Kun Bao
    Zhi, San Jun
    CHINESE CHEMICAL LETTERS, 2009, 20 (06) : 672 - 675
  • [50] Solvent-free Cleavage of tert-Butyl Esters under Microwave Conditions
    Park, Doo Han
    Park, Jung Hwan
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (01) : 230 - 232