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

被引:43
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 31 条
[1]   Stabilisation of Pd(0) on surface functionalised Fe3O4 nanoparticles: magnetically recoverable and stable recyclable catalyst for hydrogenation and Suzuki-Miyaura reactions [J].
Amali, Arlin Jose ;
Rana, Rohit Kumar .
GREEN CHEMISTRY, 2009, 11 (11) :1781-1786
[2]   Heterogenized tungsten complex: an efficient and high yielding catalyst for the synthesis of structurally diverse tetra substituted pyrrole derivatives via four-component assembly [J].
Atar, Amol B. ;
Jeong, Yeon Tae .
TETRAHEDRON LETTERS, 2013, 54 (41) :5624-5628
[3]   Lithium triflate (LiOTf): a highly efficient and reusable catalytic system for the synthesis of diversified quinolines under neat conditions [J].
Atar, Amol B. ;
Dindulkar, Someshwer D. ;
Jeong, Yeon Tae .
MONATSHEFTE FUR CHEMIE, 2013, 144 (05) :695-701
[4]   Silica supported tungstic acid (STA): an efficient catalyst for the synthesis of bis-spiro piperidine derivatives under milder condition [J].
Atar, Amol B. ;
Jeong, Yeon Tae .
TETRAHEDRON LETTERS, 2013, 54 (10) :1302-1306
[5]   Nanosized magnesium oxide as a highly effective heterogeneous base catalyst for the rapid synthesis of pyranopyrazoles via a tandem four-component reaction [J].
Babaie, Maryam ;
Sheibani, Hassan .
ARABIAN JOURNAL OF CHEMISTRY, 2011, 4 (02) :159-162
[6]   The preparation and use of novel immobilised guanidine catalysts in base-catalysed epoxidation and condensation reactions [J].
Blanc, AC ;
Macquarrie, DJ ;
Valle, S ;
Renard, G ;
Quinn, CR ;
Brunel, D .
GREEN CHEMISTRY, 2000, 2 (06) :283-288
[7]   Multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles catalyzed by lipase from Aspergillus niger [J].
Bora, Pranjal P. ;
Bihani, Manisha ;
Bez, Ghanashyam .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 92 :24-33
[8]   Tetramethylguanidine covalently bonded onto silica gel as catalyst for the addition of nitromethane to cyclopentenone [J].
DeOliveira, Edimar ;
Torres, Jocilene D. ;
Silva, Carlos C. ;
Luz, Afranio A. M. ;
Bakuzis, Peter ;
Prado, Alexandre G. S. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2006, 17 (05) :994-999
[9]  
El-Tamany ESH, 1999, J SERB CHEM SOC, V64, P9
[10]   Oxidation of 1,4-dioxane over Ti-MWW in the presence of H2O2 [J].
Fan, Weibin ;
Kubota, Yoshihiro ;
Tatsumi, Takashi .
CHEMSUSCHEM, 2008, 1 (03) :175-178