Basic isoreticular nanoporous metal–organic framework for Biginelli and Hantzsch coupling: IRMOF-3 as a green and recoverable heterogeneous catalyst in solvent-free conditions

The IRMOF-3 metal–organic framework (MOF) acts as a suitable green catalyst for the one-pot synthesis of dihydropyrimidinone and dihydropyridine derivatives through the Biginelli and Hantzsch reactions, and the desired products were obtained in high yields with short reaction times under mild solvent-free conditions. The MOFs can be isolated from the reaction mixture and reused.

[1]  S. Rostamnia,et al.  RuCl3-catalyzed solvent-free Ugi-type Groebke–Blackburn synthesis of aminoimidazole heterocycles , 2013 .

[2]  H. Xin,et al.  Metal–organic frameworks as a very suitable reaction inductor for selective solvent-free multicomponent reaction: IRMOF-3 as a heterogeneous nanocatalyst for Kabachnik–Fields three-component reaction , 2013 .

[3]  Esmail Doustkhah,et al.  Hexafluoroisopropanol dispersed into the nanoporous SBA-15 (HFIP/SBA-15) as a rapid, metal-free, highly reusable and suitable combined catalyst for domino cyclization process in chemoselective preparation of alkyl rhodanines , 2013 .

[4]  A. Pourjavadi,et al.  Water dispersed magnetic nanoparticles (H2O-DMNPs) of γ-Fe2O3 for multicomponent coupling reactions: a green, single-pot technique for the synthesis of tetrahydro-4H-chromenes and hexahydroquinoline carboxylates , 2013 .

[5]  H. Xin,et al.  Pd(OAc)2@SBA‐15/PrEn nanoreactor: a highly active, reusable and selective phosphine‐free catalyst for Suzuki–Miyaura cross‐coupling reaction in aqueous media , 2013 .

[6]  F. Kapteijn,et al.  Understanding adsorption of highly polar vapors on mesoporous MIL-100(Cr) and MIL-101(Cr): Experiments and molecular simulations , 2013 .

[7]  S. Rostamnia,et al.  SBA-15/TFE (SBA-15/2,2,2-trifluoroethanol) as a suitable and effective metal-free catalyst for the preparation of the tri- and tetra-substituted imidazoles via one-pot multicomponent method , 2012 .

[8]  A. Heydari,et al.  Nanomagnetically modified sulfuric acid (γ-Fe2O3@SiO2-OSO3H): an efficient, fast, and reusable green catalyst for the Ugi-like Groebke-Blackburn-Bienaymé three-component reaction under solvent-free conditions , 2012 .

[9]  F. Kapteijn,et al.  Interplay of metal node and amine functionality in NH2-MIL-53: modulating breathing behavior through intra-framework interactions. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[10]  A. Corma,et al.  An unexpected bifunctional acid base catalysis in IRMOF-3 for Knoevenagel condensation reactions , 2012 .

[11]  R. Butcher,et al.  Hydrogen-bonding 2D metal-organic solids as highly robust and efficient heterogeneous green catalysts for Biginelli reaction. , 2011, Tetrahedron letters.

[12]  S. Rostamnia,et al.  A Rapid, Catalyst-Free,Three-Component Synthesis of Rhodanines in Water Using Ultrasound , 2011 .

[13]  F. Kapteijn,et al.  Synthesis and Characterization of an Amino Functionalized MIL-101(Al): Separation and Catalytic Properties , 2011 .

[14]  A. Alizadeh,et al.  Adducts of Diketene, Alcohols,and Aldehydes: Useful Building Blocks for 3,4-Dihydropyrimidinonesand 1,4-Dihydropyridines , 2010 .

[15]  S. Che,et al.  Palladium nanoparticles supported on MOF-5: A highly active catalyst for a ligand- and copper-free Sonogashira coupling reaction , 2010 .

[16]  Cheng Wang,et al.  Isoreticular chiral metal-organic frameworks for asymmetric alkene epoxidation: tuning catalytic activity by controlling framework catenation and varying open channel sizes. , 2010, Journal of the American Chemical Society.

[17]  N. Phan,et al.  MOF-5 as an efficient heterogeneous catalyst for Friedel–Crafts alkylation reactions , 2010 .

[18]  C. Pinel,et al.  Solvent free base catalysis and transesterification over basic functionalised Metal-Organic Frameworks , 2009 .

[19]  F. Kapteijn,et al.  Amino-based metal-organic frameworks as stable, highly active basic catalysts , 2009 .

[20]  A. Corma,et al.  MOFs as catalysts: Activity, reusability and shape-selectivity of a Pd-containing MOF , 2007 .

[21]  Omar M. Yaghi,et al.  Metal-organic frameworks: a new class of porous materials , 2004 .

[22]  Takehisa Dewa,et al.  Enolization and Aldol Reactions of Ketone with a La3+-Immobilized Organic Solid in Water. A Microporous Enolase Mimic , 2001 .

[23]  C. Kappe.  Biologically active dihydropyrimidones of the Biginelli-type--a literature survey. , 2000, European journal of medicinal chemistry.

[24]  M. O'keeffe,et al.  Design and synthesis of an exceptionally stable and highly porous metal-organic framework , 1999, Nature.

[25]  A Hedberg,et al.  Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. , 1991, Journal of medicinal chemistry.

[26]  D. J. Triggle,et al.  New developments in calcium ion channel antagonists , 1983 .