Reusable silica supported poly phosphoric acid catalyzed three-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives

被引：107
作者：
Shaterian, Hamid Reza [1 ]
Hosseinian, Asghar [1 ]
Ghashang, Majid [1 ]
机构：
[1] Univ Sistan & Baluchestan, Fac Sci, Dept Chem, POB 98135-674, Zahedan, Iran
来源：
ARKIVOC | 2009年
关键词：
PPA-SiO2; indazolo[2,1-b]phthalazine-trione; multi-component reaction; phthalhydrazide; dimedone; ONE-POT PREPARATION; HETEROGENEOUS CATALYST; EFFICIENT; HCLO4-SIO2; HYDROGENSULFATE; CONDENSATION;
D O I：
10.3998/ark.5550190.0010.207
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives from the three-component condensation reaction of phthalhydrazide, dimedone, and aromatic aldehydes under solvent-free conditions in good to excellent yields and short reaction times using reusable silica supported poly phosphoric acid (PPA-SiO2) as heterogeneous acid catalyst has been investigated.
引用
收藏
页码：59 / 67
页数：9
相关论文
共 23 条
  • [1] Al'-Assar F., 2002, PHARM CHEM J+, V36, P598, DOI [DOI 10.1023/A:1022665331722, 10.1023/a:1022665331722]
  • [2] Silica gel-supported polyphosphoric acid (PPA/SiO2) as an efficient and reusable catalyst for conversion of carbonyl compounds into oxathioacetals and dithioacetals
    Aoyama, T
    Takido, T
    Kodomari, M
    [J]. SYNLETT, 2004, (13) : 2307 - 2310
  • [3] 3-phenyl-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-α]phthalazines and analogues:: High-affinity γ-aminobutyric acid-A benzodiazepine receptor ligands with α2, α3, and α5-subtype binding selectivity over α1
    Carling, RW
    Moore, KW
    Street, LJ
    Wild, D
    Isted, C
    Leeson, PD
    Thomas, S
    O'Connor, D
    McKernan, RM
    Quirk, K
    Cook, SM
    Atack, JR
    Wafford, KA
    Thompson, SA
    Dawson, GR
    Ferris, P
    Castro, JL
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (07) : 1807 - 1822
  • [4] Clark J.H., 2000, RSC CLEAN TECHNOL MO
  • [5] Gerard V.S., 2000, HETEROGENEOUS CATALY
  • [6] Synthesis and anticonvulsant activity of novel and potent 6,7-methylenedioxyphthalazin-1(2H)-ones
    Grasso, S
    De Sarro, G
    De Sarro, A
    Micale, N
    Zappalà, M
    Puja, G
    Baraldi, M
    De Micheli, C
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (15) : 2851 - 2859
  • [7] Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase
    Jain, RP
    Vederas, JC
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) : 3655 - 3658
  • [8] HClO4-SiO2 and PPA-SiO2 catalyzed efficient one-pot Knoevenagel condensation, Michael addition and cyclo-dehydration of dimedone and aldehydes in acetonitrile, aqueous and solvent free conditions:: Scope and limitations
    Kantevari, Srinivas
    Bantu, Rajashaker
    Nagarapu, Lingaiah
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 269 (1-2) : 53 - 57
  • [9] Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield
    Kaupp, G
    Naimi-Jamal, MR
    Schmeyers, J
    [J]. TETRAHEDRON, 2003, 59 (21) : 3753 - 3760
  • [10] Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts
    Kumar, Atul
    Maurya, Ram Awatar
    [J]. TETRAHEDRON, 2007, 63 (09) : 1946 - 1952
123