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
  • [11] Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions
    Kaboudin, B
    Nazari, R
    TETRAHEDRON LETTERS, 2001, 42 (46) : 8211 - 8213
  • [12] Microwave synthesis of AFI-type aluminophosphate molecular sieve under solvent-free conditions
    Zhao, Xinhong
    Zhao, Jiangbo
    Wen, Juanjuan
    Li, An
    Li, Guixian
    Wang, Xiaolai
    MICROPOROUS AND MESOPOROUS MATERIALS, 2015, 213 : 192 - 196
  • [13] Highly efficient cyanosilylation of aldehydes and ketones under microwave, solvent-free, and Lewis acid-free conditions
    Iida, Hirokazu
    Hamana, Hiroshi
    Matsumoto, Kiyoshi
    SYNTHETIC COMMUNICATIONS, 2007, 37 (11) : 1801 - 1805
  • [14] Microwave-assisted efficient synthesis of spiro-fused heterocycles under solvent-free conditions
    Shaabani, A
    Bazgir, A
    TETRAHEDRON LETTERS, 2004, 45 (12) : 2575 - 2577
  • [15] Heck reactions under microwave irradiation in solvent-free conditions
    DiazOrtiz, A
    Prieto, P
    Vazquez, E
    SYNLETT, 1997, (03) : 269 - &
  • [16] Synthesis of ferrocenyl Schiff bases under solvent-free conditions using microwave irradiation
    Ozturk, Gulsen
    Petit, Alain
    Kouklovsky, Cyrille
    SYNTHETIC COMMUNICATIONS, 2008, 38 (16) : 2707 - 2713
  • [17] Mild microwave-assisted hydrolysis of acetals under solvent-free conditions
    He, YH
    Johansson, M
    Sterner, O
    SYNTHETIC COMMUNICATIONS, 2004, 34 (22) : 4153 - 4158
  • [18] An efficient one-pot biginelli condensation of aliphatic aldehydes catalyzed by zinc bromide under solvent-free conditions
    Yu, Yang
    Liu, Di
    Liu, Chunsheng
    Jiang, Heng
    Luo, Genxiang
    PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY, 2007, 37 (04) : 381 - 387
  • [19] An efficient synthesis of quinolines under solvent-free conditions
    Chaudhuri, MK
    Hussain, S
    JOURNAL OF CHEMICAL SCIENCES, 2006, 118 (02) : 199 - 202
  • [20] Synthesis of polyhydroquinoline derivatives under solvent-free conditions
    Chen, WY
    Lu, J
    Jin, JR
    LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (04) : 317 - 319