95548-64-4

Upstream product

• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 2700-22-3 Benzylidenemalononitrile 
• 42963-41-7 6-hydroxyamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 100-52-7 benzaldehyde 
• 109-77-3 malononitrile 

Relevant academic research and scientific papers

Aqueous hydrotropic solution: green reaction medium for synthesis of pyridopyrimidine carbonitrile and spiro-oxindole dihydroquinazolinone derivatives

Abstract: From the green chemistry point of view, water is one of the most sustainable solvents for chemical transformations, but there are some limitations to its use as a reaction medium due to the lack of solubility of organic compounds. To overcome this difficulty, we used aqueous hydrotropic solution, which increases the solubility of organic compounds in water by?200-fold. We report an environmentally efficient method for synthesis of pyridopyrimidine carbonitriles and spiro-oxindole dihydroquinazolinones by using 50?% aqueous sodium p-toluene sulfonate (NaPTS) solution at ambient reaction condition. The merits of the present protocol include short reaction time, excellent product yield?with high purity, easy workup procedure and reusability of reaction medium. Graphical abstract: [Figure not available: see fulltext.].

One-pot synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyranes and pyridopyrimidines under mild conditions

1,8-Diazabicyclo[5.4.0]undec-7-ene immobilized on silica (SB-DBU)Cl as a reusable and heterogeneous catalyst was applied for the one-pot, three-component synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyrane-3-carbonitriles and pyridopyrimidines, under solvent-free conditions. The reaction was carried out at room temperature, and pure products were obtained in high yields and short reaction times (3–7 min). This work introduced an environmentally benign procedure for the synthesis of these classes of biological active compounds.

DABCO-based ionic liquids: Introduction of two metal-free catalysts for one-pot synthesis of 1,2,4-triazolo[4,3-a] pyrimidines and pyrido[2,3-d] pyrimidines

Straightforward methods for the synthesis of 1,2,4-triazolo[4,3-a]pyrimidine and pyrido[2,3-d]pyrimidine derivatives are described through three-component condensation of aromatic aldehydes, malononitrile, and 3-amino-1,2,4-triazole or 6-amino-1,3-dimethyluracil. In both procedures two affordable and metal-free DABCO-based ionic liquids are employed as catalysts and the obtained outcomes are compared with each other. All reactions are performed under mild conditions during acceptable reaction times in good to high yields. After ensuring the efficiency of the catalysts in both reactions, four new derivatives are synthesized and their structures are characterized by FT-IR, 1H NMR and 13C NMR. Simplicity, easy work-up procedures and recoverability of the catalysts are other advantages of these methods.

Antibacterial activity of synthetic pyrido[2,3-d]pyrimidines armed with nitrile groups: POM analysis and identification of pharmacophore sites of nitriles as important pro-drugs

A clean and simple one-pot multi-component methodology was developed for the preparation of 7-amino-2,4-dioxo-5-aryl-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitriles via the reaction of 6-amino uracil, aromatic aldehydes and malononitrile using triethylamine (TEA) base as a catalyst in aqueous ethanol medium at NTP. The reaction protocol has assorted advantages viz.; mild reaction conditions, short reaction time, environmentally friendly procedure, low cost chemicals, and easy isolation of derivatives with excellent yields of bioactive products (85-95%). All the synthesised pyrido[2,3-d]pyrimidines bearing nitrile groups (4a-4h) showed comparatively good in vitro antibacterial activities against Staphylococcus and Bacillus cereus (Gram-positive bacteria) and P. merabitis and S. maresens (Gram-negative bacteria). Nevertheless, compound 4h exhibited the highest antibacterial activity and had an excellent % inhibition as compared to standard streptomycin. Overall, compound 4h had enhanced antibacterial activity compared to its positional isomers compound 4f and compound 4g. This increase in bioactivity going from 4f (R = 4-nitro) to 4h (R = 2-nitro) is attributed to the hydrolysis of the CN to an amide which restores the vital intramolecular interaction between the ortho-nitro-phenyl and amide linkages (ONOδ?...Hδ+N) and offers a crucial template for antibacterial NH, O-pharmacophore sites. The synthesized compound 4h was tested to verify that it had fewer side effects than the standard/streptomycin. But, its possible inclusion in selective fungal/viral media viz. HIV or Hepatitis B/C is a subject of further research. This multi-component synthetic protocol uses cheap ingredients like Et3N catalyst and ethanol as the green solvent.

Efficient synthesis of pyrano[2,3-d]pyrimidinone and pyrido[2,3-d]pyrimidine derivatives in presence of novel basic ionic liquid catalyst

A basic ionic liquid, namely 1,1′-(butane-1,4-diyl)bis(1,4-diazabicyclo [2.2.2]octan-1-ium) hydroxide, was prepared and characterized using Fourier-transform infrared spectroscopy, 1H nuclear magnetic resonance spectroscopy, and pH measurements. The ionic liquid was used for efficient promotion of the synthesis of pyrano[2,3-d]pyrimidinone and pyrido[2,3-d]pyrimidine derivatives at room temperature under grinding conditions. A simple procedure, short reaction time, high yields, non-column chromatographic separation, commercial availability of the starting materials, and recyclability of the catalyst are attractive features of this process.

Synthesis and characterization of novel magnetic nanoparticles supported imidazole ion as an efficient catalytic system for the three-component reaction of arylaldehydes, malononitrile and a-hydroxy or a-amino active methylene compounds

Background: Recently, pyrimidine and chromene derivatives have concerned increasing attention because of the wide range of biological activities. Considering the prominence of pyrimidine and chromene derivatives, several procedures have been reported for the synthesis of these compounds. Herein, new magnetic nanoparticles supported ionic liquid has been evaluated for the synthesis of pyrimidine and chromene derivatives. Methods: In this method, pyrimidine and chromene compounds were synthesized by the multi-component reaction of aromatic aldehydes, malononitrile, and active methylene compounds in the presence of the new magnetic nanoparticles supported ionic liquid. The new nanocatalyst was characterized by using TEM, VSM, XRD and IR spectrum. Results: The remarkable advantages of this new procedure involve high yields, short experimental time, low cast and easy preparation of the catalyst and no need of any workup and purification. Magnetic properties of the catalyst led to the easy separation from the reaction mixture by using an external magnet. The catalyst can be reused several times in the desired reaction without significant decrease of its activity. Conclusion: An efficient and green method for the synthesis of chromene and pyrimidine compounds in the presence of magnetic nanoparticles supported ionic liquid have been developed. Thermal stability, low cost and easy synthesis of the catalyst, high yields, easy separation and purification of the product, short experimental time and using a green solvent such as water provided a useful and alternative method for such reactions.

Facile synthesis of pyridopyrimidine and coumarin fused pyridine libraries over a Lewis base-surfactant-combined catalyst TEOA in aqueous medium

A highly convergent and efficient protocol, for the facile synthesis of a library of coumarin fused pyridine and pyridopyrimidine derivatives, has been developed by applying a Lewis base-surfactant-combined catalyst (LBSC) triethanolamine (TEOA). The method described has the benefits of operational simplicity and excellent yields of the targeted molecule. The LBSCs were found to form stable colloidal dispersions rapidly in the presence of reaction substrates in water, even when the substrates are solid. In light of the increased demand for reduction of organic solvents in industry, the surfactant aided Lewis base catalysis described here may have immense practical consequences in organic synthesis. This work may not only lead to environmentally benign systems but also will provide a newer aspect of organic chemistry in water.

Structure-based design of pyridopyrimidinediones as dipeptidyl peptidase IV inhibitors

Dipeptidyl peptidase IV (DPP-4) inhibitors have been shown to enhance GLP-1 levels and thereby improve hyperglycemia in type II diabetes. From a small fragment hit, using structure-based design, we have discovered a new class of non-covalent, potent and s

One-pot, three-component condensation reaction in water: An efficient and improved procedure for the synthesis of pyran annulated heterocyclic systems

Environmentally friendly three-component condensation reactions of an activated C-H acid, an aldehyde, and alkyl nitriles to afford the corresponding pyran annulated heterocyclic systems in water in good yields, avoiding the addition of any catalyst, are reported. Copyright Taylor & Francis Group, LLC.

New strategy for the oxidation of Hantzsch 1,4-dihydropyridines and dihydropyrido[2,3-d]pyrimidines catalyzed by DMSO under aerobic conditions

A novel metal-salt-oxidant-free, efficient, and economical method for the oxidation of Hantzsch 1,4-dihydropyridines that uses aerial oxygen and solvent-grade dimethylsulfoxide is described. Also, the synthesis of pyrido[2,3-d]pyrimidines is achieved from in situ oxidation of dihydropyrido[2,3-d]pyrimidines that arise from the reaction of 6-aminouracils and cyano olefins in dimethylsulfoxide. Copyright Taylor & Francis Group, LLC.