A novel application of the oxidizing properties of urea nitrate and peroxydisulfate-cobalt(II): aromatization of NAD(P)H model Hantzsch 1,4-dihydropyridines

被引:94
作者
Anniyappan, M [1 ]
Muralidharan, D [1 ]
Perumal, PT [1 ]
机构
[1] Cent Leather Res Inst, Div Organ Chem, Adyar 600020, Chennai, India
关键词
1,4-dihydropyridines; urea nitrate; peroxydisulphate-cobalt(II); oxidation; pyridine derivatives;
D O I
10.1016/S0040-4020(02)00461-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Alkyl or aryl substituted derivatives of Hantzsch 1,4-dihydropyridine were readily oxidized by urea nitrate under microwave irradiation or refluxing conditions to the corresponding pyridine derivatives in quantitative yields. The oxidation reaction was also effected by peroxydisulfate in the presence of cobalt(II) in aqueous acetonitrile under refluxing conditions. When n-propyl, n-butyl and cinnamyl were the substituent groups in the 4-position, a mixture of 4-substituted and unsubstituted pyridines were formed. The catalysts used in the reaction are inexpensive and provide high yields in short reaction times. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5069 / 5073
页数:5
相关论文
共 36 条
  • [1] Synthesis of Hantzsch 1,4-dihydropyridines under microwave irradiation
    Anniyappan, M
    Muralidharan, D
    Perumal, PT
    [J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (04) : 659 - 663
  • [2] Urea nitrate catalyzed imino Diels-Alder reactions: Synthesis of cyclopentaquinolines, pyranoquinolines, and furoquinoline derivatives
    Anniyappan, M
    Nagarajan, R
    Perumal, PT
    [J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (01) : 99 - 103
  • [3] [Anonymous], [No title captured]
  • [4] The influences of alkyl groups in carbonyl compounds.
    Ayling, EE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1938, : 1014 - 1023
  • [5] THE MECHANISM OF THE OXIDATION OF 2-PROPANOL BY PEROXYDISULFATE ION
    BALL, DL
    CRUTCHFIELD, MM
    EDWARDS, JO
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (09) : 1599 - 1611
  • [6] CLAY-SUPPORTED REAGENT - AROMATIZATION OF 1,4-DIHYDROPYRIDINES BY CLAY-SUPPORTED METAL NITRATES
    BALOGH, M
    HERMECZ, I
    MESZAROS, Z
    LASZLO, P
    [J]. HELVETICA CHIMICA ACTA, 1984, 67 (08) : 2270 - 2272
  • [7] BiCl3 or CdI2 catalyzed Michael addition of 1,3-dicarbonyl compounds under microwave irradiations
    Baruah, B
    Boruah, A
    Prajapati, D
    Sandhu, JS
    [J]. TETRAHEDRON LETTERS, 1997, 38 (08) : 1449 - 1450
  • [8] FACILE CONVERSION OF ELECTRON RICH BENZYLIC HYDROCARBONS TO CARBONYL-COMPOUNDS BY PEROXYDISULFATE AND COPPER IONS
    BHATT, MV
    PERUMAL, PT
    [J]. TETRAHEDRON LETTERS, 1981, 22 (27) : 2605 - 2608
  • [9] Bouchr R. H., 1986, J MED CHEM, V29, P1596
  • [10] REACTIVITY OF BIOLOGICALLY IMPORTANT REDUCED PYRIDINES .4. EFFECT OF SUBSTITUTION ON FERRICYANIDE-MEDIATED OXIDATION RATES OF VARIOUS 1,4-DIHYDROPYRIDINES
    BREWSTER, ME
    SIMAY, A
    CZAKO, K
    WINWOOD, D
    FARAG, H
    BODOR, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) : 3721 - 3726