Molybdate sulfuric acid (MSA): an efficient solid acid catalyst for the synthesis of diversely functionalized fused imidazo[1,2-a]pyrimidines under solvent-free conditions

被引:26
作者
Shinde, Vijay Vilas [1 ]
Jeong, Yeon Tae [1 ]
机构
[1] Pukyong Natl Univ, Dept Image Sci & Engn, Busan 608737, South Korea
关键词
3-COMPONENT COUPLING REACTION; P-TOLUENESULFONIC ACID; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; HETEROGENEOUS CATALYSIS; ACTIVE METHYLENE; DOMINO REACTIONS; INHIBITORS; DERIVATIVES; COPPER;
D O I
10.1039/c5nj00516g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A one-pot multi-component, green, and highly efficient protocol has been developed for the synthesis of imidazo[1,2-a] pyrimidines annulated heterocyclic scaffolds (4a-4ab) using molybdate sulfuric acid (MSA) as an eco-friendly and reusable catalyst in good to excellent yields under solvent-free conditions that efficiently produced three new bonds (two C-N and one C-C) in a single operation. Other remarkable features of this environmentally benign protocol are a short reaction time, a wide range of functional group tolerance, use of an inexpensive heterogeneous catalyst, and high yield of products via a simple experimental and work-up procedure. The catalyst can be recovered and reused for at least four runs without any significant impact on the product yields. [GRAPHICS] .
引用
收藏
页码:4977 / 4986
页数:10
相关论文
共 54 条
[1]   Synthesis and SAR of a new series of COX-2-selective inhibitors:: Pyrazolo[1,5-α]pyrimidines [J].
Almansa, C ;
de Arriba, AF ;
Cavalcanti, FL ;
Gómez, LA ;
Miralles, A ;
Merlos, M ;
García-Rafanell, J ;
Forn, J .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (03) :350-361
[2]   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
[3]   Heterogeneous or homogeneous? A case study involving palladium-containing perovskites in the Suzuki reaction [J].
Andrews, SP ;
Stepan, AF ;
Tanaka, H ;
Ley, SV ;
Smith, MD .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) :647-654
[4]  
[Anonymous], 2010, ANGEW CHEM, V122, P2803, DOI [10.1002/ange.200907291, DOI 10.1002/ANGE.200907291]
[5]   Bridging homogeneous and heterogeneous catalysis with CAN•SiO2 as a solid catalyst for four-component reactions for the synthesis of tetrasubstituted pyrroles [J].
Atar, Amol B. ;
Kim, Jong Su ;
Lim, Kwon Taek ;
Jeong, Yeon Tae .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (01) :396-402
[6]  
Bahador K., 2013, J CHIN CHEM SOC-TAIP, V60, P1103
[7]   Ion Exchange Resins: Catalyst Recovery and Recycle [J].
Barbaro, Pierluigi ;
Liguori, Francesca .
CHEMICAL REVIEWS, 2009, 109 (02) :515-529
[8]   Magnesium Chelating 2-Hydroxyisoquinoline-1,3(2H,4H)-diones, as Inhibitors of HIV-1 Integrase and/or the HIV-1 Reverse Transcriptase Ribonuclease H Domain: Discovery of a Novel Selective Inhibitor of the Ribonuclease H Function [J].
Billamboz, Muriel ;
Bailly, Fabrice ;
Lion, Cedric ;
Touati, Nadia ;
Vezin, Herve ;
Calmels, Christina ;
Andreola, Marie-Line ;
Christ, Frauke ;
Debyser, Zeger ;
Cotelle, Philippe .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) :1812-1824
[9]   Imidazo[1,2-a]pyrimidines as functionally selective GABAA ligands [J].
Blackaby, WP ;
Atack, JR ;
Bromidge, F ;
Castro, JL ;
Goodacre, SC ;
Hallett, DJ ;
Lewis, RT ;
Marshall, GR ;
Pike, A ;
Smith, AJ ;
Street, LJ ;
Tattersall, DFD ;
Wafford, KA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (05) :1175-1179
[10]  
Bouma M. J., 2012, EUR J ORG CHEM, P475