176106-06-2

Usage

Chemical structure

methyl ester derivative of 4H-pyran-3-carboxylic acid

Functional groups

amino group, cyano group, methyl group, phenyl group
Potential inhibitor of monoamine oxidase (MAO) enzyme

Potential biological activities

antimicrobial, antitumor, antiviral
Potential interactions with aromatic receptors or enzymes
Applications in medicinal chemistry and drug development

Upstream product

• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 100-52-7 benzaldehyde 
• 109-77-3 malononitrile 
• 105-45-3 acetoacetic acid methyl ester 
• 67-64-1 acetone 
• 2700-22-3 Benzylidenemalononitrile 
• 124-41-4 sodium methylate 

Relevant academic research and scientific papers

Microwave-assisted liquid-phase synthesis of methyl 6-amino-5-cyano-4-aryl- 2-methyl-4H-pyran-3-carboxylate using functional ionic liquid as soluble support

A microwave-assisted liquid-phase synthesis of methyl 6-amino-5-cyano-4- aryl-2-methyl-4H-pyran-3-carboxylate was developed using functional ionic liquid as soluble support. IL-bound acetoacetate was treated with arylidenemalononitriles to give supported 4H-pyran derivatives. After cleavage, the target compounds were obtained in good yields and high purities without chromatographic purification.

Microwave promoted, sodium acetate catalyzed one pot synthesis of poly functionalized 4H-pyrans

A clean and efficient one pot synthesis of 4H-pyran derivatives through condensation of aromatic aldehydes, malononitrile and dicarbonyl compounds under microwave irradiation in presence of Sodium acetate as a catalyst is described.

New application of decaniobate salt as basic solid in the synthesis of 4H-pyrans by microwave assisted multicomponent reactions

This study focuses on the search of new applications of polyoxometalates known as decaniobate ions [Nb10O28]6?. The decaniobates can be used as basic solid catalysts in multicomponent reactions to obtain good yields to 4H-pyrans (> 95%) under microwave radiation and solvent-free conditions, using several aldehydes with different electron-withdrawing or electron donor substituents. The synthesis of (TMA)6 [Nb10O28]6H2O was performed following a simple protocol (HPNb), which was modified to decrease the number of hexaniobate species that are formed as impurities (HPNb-HF).

Microwave-promoted synthesis of 2-amino-4-aryl-4H-pyrans on soluble polymeric support

2-Amino-4-aryl-4H-pyran derivatives could be prepared rapidly and smoothly in good to excellent yields by the microwave-assisted liquid-phase strategy of multicomponent synthesis on polyethylene glycol. Copyright Taylor & Francis, Inc.

Synthesis of mesoporous Ca-MCM catalysts and their use in suitable multicomponent synthesis of polyfunctionalized pyrans

Mesoporous Ca-MCM catalysts were prepared using a mixture of CaCO3, TEOS, cetyl trimethyl ammonium bromide (CTAB), triethanolamine (TEA), ethanol and H2O. Three catalysts with different CaCO3 contents, M-Ca 1?%, M-Ca 5?% and M-Ca 10?%, respectively, were prepared and characterized by N2 physisorption, XRD, FT-IR, XPS, TPD-CO2 and Pyridine-FTIR. A green and simple protocol was developed for the synthesis of 6-amino-4H-pyran scaffolds through a multicomponent coupling reaction of an aldehyde, malononitrile, and 1,3-dicarbonyl compound in different reaction solvents. This procedure was performed at room temperature (20?°C), obtaining good and excellent yields of 4H-pyran derivatives. The mesoporous materials are insoluble in polar media, which allows easy removal of the reaction products without affecting their catalytic activity. The leaching test showed an excellent stability, and Ca-MCM catalysts can be used three times without appreciable loss of their catalytic activity.

Green synthesis and antibacterial, antifungal activities of 4H-pyran, tetrahydro-4H-chromenes and spiro2-oxindole derivatives by highly efficient Fe3O4@SiO2@NH2@Pd(OCOCH3)2 nanocatalyst

An efficiently, magnetically retrievable Fe3O4@SiO2@NH2@Pd(OCOCH3)2 nanoparticles was successfully synthesized and affirmed by several physicochemical characterization tools, such as scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-disoersive X-ray spectroscopy (EDX), Fourier-transform infrared spectroscopy (FT-IR), and power X-ray diffraction. Thereafter, the catalytic performance of this environmentally benign nanocatalyst was investigated in the one-pot multicomponent synthesis of biologically important 2-amino-3-cyano-4H-pyran, tetrahydro-4H-chromenes and spiro2-oxindole derivatives. The reaction was simply achieved via one-pot three-component reaction of arylaldehydes, malononitrile and dimedone/isatins/methylaceto acetate ethanol at room temperature, with excellent yields and high purity. A new catalytic system, recyclability of reaction medium, little reaction times and excellent yields with easy workup render this protocol more attractive and economically viable.

Synthesis and antibacterial study of 2-amino-4H-pyrans and pyrans annulated heterocycles catalyzed by sulfated polysaccharide-coated BaFe12O19 nanoparticles

Abstract: In this procedure, the synthesis of ecofriendly, magnetically retrievable BaFe12O19 was reported using a sulfated polysaccharide of?algal origin, Irish moss (IM), as bio-matrix and capping agent. The characterization of BaFe12O19@IM was performed by some physicochemical characterization tools, such?as Fourier transform?infrared spectroscopy, X-ray powder diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, vibrating sample magnetometer, and thermogravimetric analysis. The catalytic performance and recyclability of the introduced heterogeneous catalyst have been explored in the one-pot synthesis of 2-amino-4H-pyrans and pyrans annulated heterocyclic compounds via a three-component reaction between aldehydes, malononitrile, and various C–H activated acidic compound under green reaction conditions. This environmentally benign catalyst displayed high catalytic activity and effective reusability and could maintain its high catalytic efficiency even after six recycling runs. Furthermore, the antibacterial activity of BaFe12O19@IM and the selected compound (4a) toward two types of clinically isolated bacterial strains Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) was evaluated. The results revealed that BaFe12O19@IM and 2-amino-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (4a) showed an effective antibacterial activity against gram-positive S. aureus. Graphic abstract: [Figure not available: see fulltext.].

A Novel Biopolymer-based Nanomagnetic Catalyst for the Synthesis of 4H-pyran and Tetrahydro-4H-chromene Derivatives

In the present study, we have designed and synthesized a new magnetically recoverable, nanocatalyst of Ag/Fe3O4?starch. The successful synthesis and the structure of the nanocatalyst were confirmed and evaluated with several analytical techniques including XRD, EDX, VSM, FT-IR, TEM and TGA. The impact and efficiency of Ag/Fe3O4?starch were successfully investigated in the one-pot synthesis of desired 4H-pyrans and tetrahydro-4H-chromenes using three-component condensation of various aldehydes, malononitrile, and 1,3-diketoesters or cyclic 1,3-diketones. The magnetic nanocatalyst was easily recovered and reused with high catalytic activity even after up to five runs.

Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4: H -chromenes

Immobilized piperazine on the surface of graphene oxide (piperazine-GO) is synthesized and characterized by different methods such as FT-IR, solid-state 29Si{1H} and 13C{1H} CP/MAS NMR, elemental analysis, TGA, TEM, FE-SEM, XPS, and TPD. Subsequently, it is used as a heterogeneous bifunctional acid-base catalyst for the efficient multicomponent reaction of malononitrile, different active compounds containing enolizable C-H bonds and various aryl/alkyl aldehydes in aqueous ethanol. A wide variety of 2-amino-3-cyano-4H-chromenes are synthesized in the presence of this heterogeneous catalyst in good to high yields and with short reaction times. The catalyst is easily separated and reused for at least six times without significant loss of activity. The acidic nature of GO improves the catalytic activity of the supported piperazine and also provides heterogeneity to the catalyst. Use of aqueous ethanol as a green solvent, high turnover numbers (TON), facile catalyst recovery and reuse, simple work-up and generality of the method make this protocol an environmentally benign procedure for the synthesis of the title heterocycles.

Ferric Sulfasalazine Sulfa Drug Complex Supported on Cobalt Ferrite Cellulose; Evaluation of Its Activity in MCRs

Abstract: The green and nano catalyst was simply prepared through the reaction of ferric sulfasalazine with nanomaterial CoFe2O4-cellulose as a magnetic biopolymer surface. This novel heterogeneous organometallic catalyst was charact