193887-94-4Relevant articles and documents
Efficient and facile ‘on-solvent’ multicomponent synthesis of medicinally privileged pyrano[3,2-c]pyridine scaffold
Elinson, Michail N.,Ryzhkov, Fedor V.,Vereshchagin, Anatoly N.,Goloveshkin, Alexander S.,Bushmarinov, Ivan S.,Egorov, Mikhail P.
, p. 3199 - 3209 (2018)
The new type of ‘on-solvent’ multicomponent reaction was found: transformation of benzaldehydes, malononitrile and 4–hydroxy-6-methylpyridin-2(1H)-one in the presence of sodium acetate as catalyst in a small amount of ethanol results in formation of substituted 2-amino-7-methyl-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles in excellent 92–99% yields. This novel ‘one-pot’ process opens an efficient and convenient way to functionalize pyrano[3,2-c]pyridine systems, which are promising compounds for different biomedical applications.
One-pot synthesis of 2-amino-4: H -chromene derivatives by MNPs@Cu as an effective and reusable magnetic nanocatalyst
Ma, Wanzheng,Ebadi, Abdol Ghaffar,Sabil, Mostafa Shahbazi,Javahershenas, Ramin,Jimenez, Giorgos
, p. 12801 - 12812 (2019/05/10)
In this research, MNPs@Cu as an effective and recyclable nanocatalyst was prepared and characterized using different methods including Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), vibrating sample magnetometry (VSM),
(CTA)3[SiW12]-Li+-MMT: A novel, efficient and simple nanocatalyst for facile and one-pot access to diverse and densely functionalized 2-amino-4H-chromene derivatives via an eco-friendly multicomponent reaction in water
Abbaspour-Gilandeh, Esmayeel,Aghaei-Hashjin, Mehraneh,Yahyazadeh, Asieh,Salemi, Hadi
, p. 55444 - 55462 (2016/07/06)
A simple, facile and highly efficient one-pot synthesis of a pharmaceutically interesting diverse kind of functionalized 2-amino-4H-chromene by a straightforward three-component reaction of an aromatic aldehyde, malononitrile (or ethyl cyanoacetate) and diverse enolizable C-H activated acidic compounds in the presence of a catalytic amount of (CTA)3[SiW12]-Li+-MMT is reported as a novel, environmentally friendly, reusable and promising nanocatalyst reaction in refluxing water. Based on the procedure, it was feasible to synthesize 2-amino-3-cyano-pyrano[3,2-c]chromen-5(4H)-one (4a-4y), 2-amino-3-cyano-pyrano[3,2-c]quinolin-5(4H)-one (6a-6s), 2-amino-3-cyano-7,8-dihydro-4H-chromen-5(6H)-one (8a-8u), 2-amino-3-cyano-pyrano[4,3-b]pyran-5(4H)-one (12a-12f), 2-amino-3-cyano-pyrano[3,2-c]pyridine-6(5H)-one (13a-13f), and 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-dione (14a-14f). The structure of the nanocatalyst was confirmed by various techniques such as IR, SEM, TGA-DTG, EDX, ICP and XRD analyses. In comparison to the conventional methods, the salient features of the present protocol are green reaction conditions, high quantitative yields, short reaction time, high atom economy, low cost, easy isolation of products, and no column chromatographic separation.
Synthesis, characterization, and application of Cu2O and NiO nanoparticles supported on natural nanozeolite clinoptilolite as a heterogeneous catalyst for the synthesis of pyrano[3,2-b]pyrans and pyrano[3,2-c]pyridones
Baghbanian, Seyed Meysam
, p. 59397 - 59404 (2015/02/19)
In this research, Cu2O and NiO nanoparticles supported on natural nanozeolite clinoptilolite (CP) was found to be a recoverable catalyst system for synthesis of pyrano-[3,2-c]pyridone and pyrano[3,2-b]pyran derivatives in aqueous media. The nan
Practical and efficient synthesis of pyrano[3,2-c]pyridone, pyrano[4,3-b]pyran and their hybrids with nucleoside as potential antiviral and antileishmanial agents
Fan, Xuesen,Feng, Dong,Qu, Yingying,Zhang, Xinying,Wang, Jianji,Loiseau, Philippe M.,Andrei, Graciela,Snoeck, Robert,Clercq, Erik De
supporting information; experimental part, p. 809 - 813 (2010/05/18)
A highly practical and efficient preparation of pyrano[3,2-c]pyridone and pyrano[4,3-b]pyran derivatives was developed via an ionic liquid mediated and promoted multi-component reaction of aldehyde (1), 4-hydroxy-pyridin-2(1H)-one or 4-hydroxy-2-pyranone (2), and malononitrile (3). As an application, a series of pyrimidine nucleoside-pyrano[3,2-c]pyridone or pyrano[4,3-b]pyran hybrids were efficiently obtained. These hybrid compounds were evaluated as potential antiviral and antileishmanial agents and showed encouraging biological activities.
General method for the preparation of substituted 2-amino-4H,5H-pyrano[4,3- b]pyran-5-ones and 2-Amino-4H-pyrano[3,2-c]pyridine-5-ones
Stoyanov, Edmont V.,Ivanov, Ivo C.,Heber, Dieter
, p. 19 - 32 (2007/10/03)
Reaction of 4-hydroxy-6-methyl-2-pyrone (1a) as well as 4-hydroxy-6-methyl-2(1H)-pyridones (1b-d) with arylmethylene malononitriles or arylmethylene methyl cyano-acetates (2a-h) leads to the formation of the very stable 5,6-fused bicyclic 2-amino-4H-pyran
Synthesis of Functionalized 4H-Pyrano[3,2-c]pyridines from 4-Hydroxy-6-methyl-2-pyridone and Their Reactions. Unexpected New Routes to 3,3′-Benzylidenebis[4-hydroxy-6-methyl-2(1H)-3-pyridinone]s
Mekheimer, Ramadan Ahmed,Mohamed, Nabil Helmi,Sadek, Kamal Usef
, p. 1625 - 1630 (2007/10/03)
The reaction of 4-hydroxy-6-methyl-2-pyridone 1 with benzylidenemalononitriles in an ethanolic solution containing a catalytic amount of piperidine and α-cyanoacrylic esters in pyridine affords the corresponding 4H-pyrano[3,2-c]pyridines. However, it's reaction with 3-(cyanomethylene)-2-indolinones gives either 2-amino-3-quinolinecarbonitriles or ethyl 2-amino-5′,6′-dihydro-7′-methyl-2,5′-dioxospiro- [indoline-3,4′-[4H]-pyrano[3,2-c]pyridine-3′-carboxylate. In contrast, the reaction of 1 with 3-aryl-2-cyano-2-propenethioamides affords 3,3′-benzylidenebis[4-hydroxy-6-methyl-2(1H)-3-pyridinone]s. The reaction of the obtained 4H-pyrano[3,2-c]pyridines with acetic anhydride affords the corresponding fused system.
