A green and one-pot synthesis of a library of 1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using thiourea dioxide (TUD) as an efficient and reusable organocatalyst

被引:31
作者
Vekariya, Rajesh H. [1 ]
Patel, Kinjal D. [1 ]
Patel, Hitesh D. [1 ]
机构
[1] Gujarat Univ, Sch Sci, Dept Chem, Ahmadabad 380009, Gujarat, India
关键词
1,4-Dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives; Thiourea dioxide (TUD); One-pot synthesis; Aqueous-phase synthesis; Organocatalysis; MULTICOMPONENT SYNTHESIS; RECYCLABLE CATALYST; 4-COMPONENT SYNTHESIS; ACID; ACTIVATION; PYRAZOLE; DESIGN; MILD;
D O I
10.1007/s11164-015-2308-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The efficacy of thiourea dioxide (TUD) as an efficient, inexpensive, and readily accessible organocatalyst for the synthesis of 1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives via a four-component reaction of ethyl acetoacetate, hydrazine hydrate, aryl aldehydes, and malononitrile is described. Upon completion of the reaction, the product was isolated by filtration, and the remaining aqueous TUD solution could be reused several times with consistent catalytic activity. High yields, simple work-up process, avoiding the use of organic solvents, short reaction time, and recyclable catalyst are the superior advantages of the present protocol. [GRAPHICS] .
引用
收藏
页码:4683 / 4696
页数:14
相关论文
共 81 条
  • [11] Nano-titania-supported Preyssler-type heteropolyacid: An efficient and reusable catalyst in ultrasound-promoted synthesis of 4H-chromenes and 4H-pyrano[2,3-c]pyrazoles
    Azarifar, Davood
    Khatami, Seyed-Mola
    Nejat-Yami, Razieh
    [J]. JOURNAL OF CHEMICAL SCIENCES, 2014, 126 (01) : 95 - 101
  • [12] Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus
    Barbas, Carlos F., III
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 42 - 47
  • [13] Organocatalysis-after the gold rush
    Bertelsen, Soren
    Jorgensen, Karl Anker
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2178 - 2189
  • [14] Synthesis, cytotoxic, and DNA binding studies of novel fluorinated condensed pyrano pyrazoles
    Bhavanarushi, S.
    Kanakaiah, V.
    Yakaiah, E.
    Saddanapu, V.
    Addlagatta, A.
    Rani, J. Vatsala
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (05) : 2446 - 2454
  • [15] Bhosale VN, 2014, J CHEM PHARM RES, V6, P733
  • [16] Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles in Ethanol
    Bihani, Manisha
    Bora, Pranjal P.
    Bez, Ghanashyam
    Askari, Hassan
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (04): : 440 - 447
  • [17] Multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles catalyzed by lipase from Aspergillus niger
    Bora, Pranjal P.
    Bihani, Manisha
    Bez, Ghanashyam
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 92 : 24 - 33
  • [18] Brahmachari G., 2013, CHEM ENG, V2, P411
  • [19] Multi-component syntheses of heterocycles by transition-metal catalysis
    D'Souza, Daniel M.
    Mueller, Thomas J. J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1095 - 1108
  • [20] Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo
    de Andrade-Neto, VF
    Goulart, MOF
    da Silva, JF
    da Silva, MJ
    Pinto, MD
    Pinto, AV
    Zalis, MG
    Carvalho, LH
    Krettli, AU
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) : 1145 - 1149