111253-25-9

Upstream product

• 2475-92-5 4-methoxyacetophenone oxime 
• 100-52-7 benzaldehyde 
• 109-77-3 malononitrile 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 959-23-9 4'-methoxychalcone 

Downstream Products

• 111253-36-2 4-Imino-7-(p-methoxyphenyl)-5-phenyl-3-(p-tolyl)pyrido<2,3-d>pyrimidine-2(1H)-thione 
• 111253-31-7 3,5-Diphenyl-4-imino-7-(p-methoxyphenyl)pyrido<2,3-d>pyrimidine-2(1H)-thione 
• 111253-32-8 3-(p-Chlorophenyl)-4-imino-7-(p-methoxyphenyl)-5-phenylpyrido<2,3-d>pyrimidine-2(1H)-thione 
• 111253-34-0 4-Imino-7-(p-methoxyphenyl)-5-phenyl-3-(o-tolyl)pyrido<2,3-d>pyrimidine-2(1H)-thione 
• 111253-35-1 4-Imino-7-(p-methoxyphenyl)-5-phenyl-3-(m-tolyl)pyrido<2,3-d>pyrimidine-2(1H)-thione 
• 111253-33-9 3-(p-Bromophenyl)-4-imino-7-(p-methoxyphenyl)-5-phenylpyrido<2,3-d>pyrimidine-2(1H)-thione 

Relevant academic research and scientific papers

Amberlyst-15 catalysed sonochemical synthesis of 2-amino-4,6-disubstituted nicotinonitrile derivatives and their biological evaluation

The 2-amino nicotinonitrile framework has been explored first time for the identification of potential inhibitors of SIRT1. Thus a series of targeted 2-amino-4,6-disubstituted nicotinonitrile derivatives were synthesized by employing an ultrasound assisted MCR of ketones, aldehydes, malononitrile and ammonium acetate. The MCR was carried out in the presence of Amberlyst-15 in MeCN under mild conditions to give the desired product in good yields. The reaction was less efficient in the absence of air whereas combination of Amberlyst-15, ultrasound, air and MeCN was essential for the success of this MCR. Several of the synthesized compounds showed good activities when tested for their SIRT1 inhibitory potential in vitro among which 5c, 5e and 5n were identified as the most potent (IC50 ~ 3 μM) and were better than the known inhibitor nicotinamide (IC50 ~109 μM). In the in silico docking studies these three compounds showed better binding energy (> 100 kcal/mol) and higher number of interactions than nicotinamide (binding energy -88.38 kcal/mol). While both amino (–NH2) and cyano (–CN) groups of nicotinonitrile derivatives formed H-bonds with the ASN346 and HIS363 residue respectively the nicotinamide showed similar interactions with ASP348 and ILE347 through its amide (–CONH2) moiety. Compound 5c, 5e and 5n has been identified as initial hits for further study.

β-Cyclodextrin: A supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1 H)-one

β-Cyclodextrin, a green and widespread supramolecular catalyst, has been explored as a highly proficient promoter for the metal-free one-pot multi-component synthesis of a vast range of highly functionalized bioactive heterocyclic moiety, 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one, from easily available precursor aldehydes. The main endeavor of these protocols is to explore this organic supramolecule in one-pot multi-component synthesis. Absence of metal catalyst or toxic acid and harsh reaction conditions, excellent functional group tolerance, inexpensive, greener and environmentally safe protocol are the key advantages of this work.

Synthesis of a novel acidic ionic liquid catalyst and its application for preparation of pyridines via a cooperative vinylogous anomeric-based oxidation

Abstract: In the current study, a novel acidic ionic liquid catalyst based on 8-hydroxyquinoline, namely 8,8′,8″-([1,3,5-triazine-2,4,6-triyl]tris[oxy])tris(1-sulfoquinolin-1-ium)chloride (TTS), was designed and synthesized. The structure of the prepared acidic ionic liquid (AIL) was fully investigated by using Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray (EDX) analysis, thermogravimetric analysis/differential thermal analysis (TGA/DTA), 1HNMR, 13CNMR and mass spectroscopy. Then, the catalytic performance of described AIL was successfully inspected toward the four-component synthesis of pyridine derivatives via a cooperative vinylogous anomeric-based oxidation. Graphic abstract: Novel AIL (TTS) showed a very high efficiency in the synthesis of pyridines. [Figure not available: see fulltext.].

One-pot synthesis of 2-amino-3-cyanopyridines and hexahydroquinolines using eggshell-based nano-magnetic solid acid catalyst via anomeric-based oxidation

Abstract: In the present research, the eggshell as a hazardous waste by European Union regulations was converted to a valuable catalyst, namely nano-Fe3O4@(HSO4)2. The as-prepared catalyst, first, was characterized using different techniques, including Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX), field emission scanning electron microscopy (FESEM), and transmission electron microscopy (TEM). Back-titration method confirmed the loading of a high surface density of acidic group, namely 8.8?mmol HSO4 per gram of the catalyst. The catalytic property of the as-prepared catalyst was examined in the synthesis of 2-amino-3-cyanopyridines via anomeric-based oxidation (ABO), and hexahydroquinolines derivatives. High yield, short reaction time, solvent-free condition, waste to wealth, and optimization with the design of experiment are the major advantages of the present work. Taken together, these results suggest the conversion of waste to wealth products around the world and usage in organic transformation. Graphic abstract: [Figure not available: see fulltext.].

Catalyst-free three-component synthesis of 2-amino-4,6-diarylpyridine-3-carbonitriles under solvent-free conditions

[Figure not available: see fulltext.] A novel efficient one-pot synthesis of 2-amino-4,6-diarylpyridine-3-carbonitriles is described. Method involves heating the mixture of an acetophenone oxime, aldehyde, and malononitrile without any catalyst under solvent-free conditions to give the title compounds in good to high yields.

The green synthesis of 2-amino-3-cyanopyridines using SrFe12O19 magnetic nanoparticles as efficient catalyst and their application in complexation with Hg2+ ions

Abstract: In this paper, a family of 2-amino-4,6-diphenylnicotinonitriles are prepared from aromatic aldehydes, acetophenone derivatives, malononitrile, and ammonium acetate via one-pot reaction catalyzed by SrFe12O19 magnetic nanoparticles. SrFe12O19 was an efficient, green, and reusable nanomagnetic heterogeneous catalyst with the average particles’ size of 70?nm which can be recycled and readily and separated from the reaction mixture using an external magnet. Short reaction times and high yields of desired products are the main advantages of the presented procedure. Subsequently, the spectrophotometric method was used to investigation of the complexation process between 2-amino-4,6-diphenylnicotinonitrile as organo-ligand and several metal ions such as Ag+, Cd2+, Co2+, Cr3+, Cu2+, Fe3+, Hg2+, Mn2+, Ni2+, Pb2+, and Zn2+ in CH3CN solution at 25?°C. According to the obtained results, the absorption spectra of organo-ligand in the CH3CN solution only were changed by the addition of Hg2+ ions, which indicates the formation of one absorbing complex compound between organo-ligand and Hg2+ ions. The stoichiometry of the resulting complex was calculated from the computer fitting of the molar absorbance measurements in different mole ratios. Graphical abstract: [Figure not available: see fulltext.].

A multicomponent synthesis of 2-amino-3-cyanopyridine derivatives catalyzed by heterogeneous and recyclable copper nanoparticles on charcoal

An efficient and convenient method was developed for synthesis of 2-amino-3-cyanopyridine derivatives via the four-component coupling reaction between ketone, aldehyde, malononitrile, and ammonium acetate in the presence of 2 molpercent copper nanoparticles on charcoal (Cu/C) catalyst. A variety of ketones and aldehydes was used to afford the corresponding products in good to excellent yields. The method is applicable to large-scale operation without any problem. The catalyst could be quantitatively recovered from the reaction mixture by simple filtration and reused at least eight times with almost consistent activity.

Graphene oxide: A reusable and metal-free carbocatalyst for the one-pot synthesis of 2-amino-3-cyanopyridines in water

A one-pot synthesis of 2-amino-3-cyanopyridine derivatives has been demonstrated through the multicomponent reaction of aldehydes, ketones, malononitrile, and ammonium acetate using graphene oxide as a heterogeneous catalyst in water as a green medium. The graphene oxide catalyst is very mild, effective, and most of its activity is preserved after being reused for five times.

Novel Bu4N+Br- catalyzed one-pot multi-component synthesis of 2-amino nicotinonitriles in aqueous medium

Abstract An efficient single-pot strategy for 2-amino nicotinonitrile derivatives 5 has been developed by multi-component reaction of arylaldehydes 1, methylketones 2, malononitrile 3, and ammonium acetate 4 using tetrabutyl ammonium bromide as catalyst in aqueous medium.