SYNTHESIS OF 6-AMINO-2,4-DIHYDROPYRANO[2,3-c]PYRAZOL-5-CARBONITRILES CATALYZED BY SILICA-SUPPORTED TETRAMETHYLGUANIDINE UNDER SOLVENT-FREE CONDITIONS

被引:42
|
作者
Atar, Amol B. [1 ]
Kim, Jong Tae [1 ]
Lim, Kwon Taek [1 ]
Jeong, Yeon Tae [1 ]
机构
[1] Pukyong Natl Univ, Dept Image Sci & Engn, Pusan 608737, South Korea
关键词
Four-component reaction; heterogeneous catalyst; pyrano[2; 3-c]pyrazole; silica-supported tetramethylguanidine; ONE-POT SYNTHESIS; MULTICOMPONENT SYNTHESIS; HIGHLY EFFICIENT; RAPID SYNTHESIS; PYRANOPYRAZOLES; 4-COMPONENT; DERIVATIVES; CONDENSATION; GEL;
D O I
10.1080/00397911.2014.913634
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, high-yielding, and rapid protocol has been developed for the synthesis of diversity-oriented 6-amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles derivatives via a four-component, one-pot cyclocondensation reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile using silica-supported tetramethylguanidine as a heterogeneous catalyst for the first time. The protocol proves to be efficient and environmentally benign in terms of very easy workup, good yields, and ease of recovery of catalyst. In addition, the present method is superior in terms of green media, the amount of catalyst, and reaction time.
引用
收藏
页码:2679 / 2691
页数:13
相关论文
共 50 条
  • [41] An Efficient and Green Synthesis of 6-Amino-3-phenyl-4-aryl-1,4-dihydropyrano [2,3-c]pyrazole-5-carbonitrile Derivatives under Ultrasound Irradiation in Aqueous Medium
    Zou, Yi
    Hu, Yu
    Liu, Hai
    Shi, Da-Qing
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (05) : 1174 - 1179
  • [42] Environmentally benign synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c] pyrazole-3-carboxylates using CeO2 nanoparticles as a reusable and robust catalyst
    Safaei-Ghomi, Javad
    Asgari-Kheirabadi, Mehrnoosh
    Shahbazi-Alavi, Hossein
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2016, 71 (11): : 1135 - 1140
  • [43] Synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using nano-ZnZr4(PO4)(6) as an efficient catalyst
    Safaei-Ghomi, Javad
    Asgari-Kheirabadi, Mehrnoosh
    Shahbazi-Alavi, Hossein
    Ziarati, Abolfazl
    IRANIAN JOURNAL OF CATALYSIS, 2016, 6 (04): : 319 - 324
  • [44] A facile synthesis of 6-amino-2H, 4H-pyrano[2,3-c]pyrazole-5-carbonitriles in deep eutectic solvent
    Bhosle, Manisha R.
    Khillare, Lalit D.
    Dhumal, Sambhaji T.
    Mane, Ramrao A.
    CHINESE CHEMICAL LETTERS, 2016, 27 (03) : 370 - 374
  • [45] D,L-proline-catalyzed one-pot synthesis of pyrans and pyrano[2,3-c]pyrazole derivatives by a grinding method under solvent-free conditions
    Guo, Shao-Bo
    Wang, Shu-Xiang
    Li, Ji-Tai
    SYNTHETIC COMMUNICATIONS, 2007, 37 (13) : 2111 - 2120
  • [46] Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[α]pyrano[2,3-c]phenazine]and benzo[α]pyrano[2,3-c]phenazine derivatives under solvent-free conditions
    Afshin Yazdani-Elah-Abadi
    Malek-Taher Maghsoodlou
    Razieh Mohebat
    Reza Heydari
    ChineseChemicalLetters, 2017, 28 (02) : 446 - 452
  • [47] Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[a]pyrano[2,3-c]phenazine] and benzo[a]pyrano[2,3-c]phenazine derivatives under solvent-free conditions
    Yazdani-Elah-Abadi, Afshin
    Maghsoodlou, Malek-Taher
    Mohebat, Razieh
    Heydari, Reza
    CHINESE CHEMICAL LETTERS, 2017, 28 (02) : 446 - 452
  • [48] X-Ray Crystal Structure Analysis of Novel 6-Amino-3-Phenyl-4-(Pyridin-4-yl)-2,4-Dihydropyrano[2,3-c]pyrazole-5-Carbonitrile
    S. Sharma
    G. Brahmachari
    V. K. Gupta
    Crystallography Reports, 2020, 65 : 1202 - 1207
  • [49] Efficient synthesis of 3,4-dihydropyrano[3,2-c]chromenes catalyzed by Ni(II)-functionalized Li+-Montmorillonite in a one-pot fashion under solvent-free conditions
    Azizi, Hashem
    Khorshidi, Alireza
    Tabatabaeian, Khalil
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (05) : 1023 - 1032
  • [50] Synthesis and crystal structure of 3-methyl-5-cyano-6-amino-1-phenyl-4-(3,4-dimethoxylphenyl)-1,4-dihydropyrano[2,3-c]pyrazole
    Wang, XS
    Shi, DQ
    Rong, LC
    Yao, CS
    Dai, GY
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2003, 22 (03) : 331 - 335