38477-51-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 98-86-2 acetophenone 
• 109-77-3 malononitrile 
• 2826-26-8 2-(4-methoxyphenylmethylene)malononitrile 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 2972-85-2 2-(1-(4-methoxyphenyl)ethylidene)malononitrile 
• 156605-56-0 1-phenylethan-1-one O-pivaloyl oxime 
• 613-91-2 acetophenone oxime 
• 19433-17-1 (E)‐1‐phenylethan‐1‐one O‐acetyl oxime 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 169698-78-6 C₁₉H₁₄N₂O 

Downstream Products

• 129769-70-6 4-Imino-5-(4-methoxy-phenyl)-3,7-diphenyl-3,4-dihydro-1H-pyrido[2,3-d]pyrimidine-2-thione 
• 132814-27-8 3-(4-Fluoro-phenyl)-4-imino-5-(4-methoxy-phenyl)-7-phenyl-3,4-dihydro-1H-pyrido[2,3-d]pyrimidine-2-thione 
• 132814-29-0 3-(4-Ethoxy-phenyl)-4-imino-5-(4-methoxy-phenyl)-7-phenyl-3,4-dihydro-1H-pyrido[2,3-d]pyrimidine-2-thione 
• 132814-28-9 3-(2-Ethoxy-phenyl)-4-imino-5-(4-methoxy-phenyl)-7-phenyl-3,4-dihydro-1H-pyrido[2,3-d]pyrimidine-2-thione 
• 132814-26-7 3-(4-Bromo-phenyl)-4-imino-5-(4-methoxy-phenyl)-7-phenyl-3,4-dihydro-1H-pyrido[2,3-d]pyrimidine-2-thione 

Relevant academic research and scientific papers

Improved Synthesis of 2-Amino-3-cyanopyridines in Solvent Free Conditions under Microwave Irradiation

A simple and efficient method is developed for the rapid synthesis of 2-amino-3-cyanopyridines 3-5 from arylidenemalanonitriles 1 and ketones 2 or 4 in presence of ammonium acetate without solvent/containing traces of solvent under microwave irradiation:

Synthesis and anticancer assessment of some new 2-amino-3-cyanopyridine derivatives

The 2-Aminonicotinonitrile derivative was reacted with different bi-functional reagents such as formamide, thiourea, acetic anhydride, and phthalic anhydride under optimized conditions to give pyrimidine, thiourea, acetamide, and isoindoline derivatives, respectively, When it was treated with active methylene reagents as malononitrile, phenacyl bromide, and ethyl bromoacetate under varied experimental modulation, it afforded 1, 8-naphthyridine, ethyl, and methylamino nicotinonitrile derivatives, respectively. Also, it was reacted with p-toluene sulfonyl chloride, chloroacetyl chloride, and benzoyl chloride to give sulfonamide, 2-chloro-N-acetamide, and benzamide derivatives, respectively. Likewise, it was reacted with diethyl malonate, ethyl cyanoacetate, and cyano acetic acid to give ethylpropanoate, naphthyridine, and cyano acetamide derivatives, respectively. However, treatment of ethylpropanoate and cyano acetamide derivatives with hydrazine hydrate gave pyrazole and 5-amino-pyrazole nicotinonitrile derivatives, respectively. In addition, it was reacted with p-anisaldehyde, phenyl isocyanate, and triethyl orthoformate to give benzylamino nicotinonitrile, phenyl urea, and N-formamide derivatives, respectively. Furthermore, it was reacted with nitrous acid then coupled with aniline; it was also reacted with isatine and 1,3- dibromo propane to give oxoindoline derivative, and the dimer. Elemental analyses, together with spectroscopic data including IR, 1H-NMR in addition to 13C-NMR and mass spectra submit proofs for the chemical structures for all compounds.

Application of salicylic acid as an eco-friendly and efficient catalyst for the synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives

In this study, three eco-friendly, efficient, and convenient protocols have been reported for one-pot synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives using salicylic acid as a catalyst under solvent-free condition. The reported protocols offer several significant advantages such as the application of a nontoxic, neutral, and cheap catalyst, environmentally friendly conditions, the easy isolation of products by filtering, short reaction times, simple methodology, and good yields.

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.

Green synthesis of 2-amino-3-cyanopyridines via a cooperative vinylogous anomeric-based oxidation and their antiproliferative effects on liver, breast, and prostate cancer studies

2-Amino-3-cyanopyridine derivatives were synthesized in an ultrasonic bath and one pot four-component reactions with high yields, in a short time, without solvent and catalyst, and anticancer activity studies on MCF7, DU145, and HepG2 cell lines were inve

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.].

Facile microwave-assisted preparation of an ester-based cationic gemini surfactant for the improved micellar synthesis of aminocyanopyridines

In this work, a diester cationic gemini surfactant (DCGS) was prepared from the reaction of N,N-dimethyldodecylamine with the microwave (MW)-assisted synthesized spacer ethane-1,2-diyl bis(2-chloroacetate) (EDBC) by the three-component reaction of ethylene glycol with chloroacetic acid (2 equiv.) under MW-irradiation. The structure of the spacer EDBC and surfactant DCGS were evaluated by 1H NMR, FT-IR, melting point, surface tension (γ), pendant drop, and critical micelle concentration (CMC) analysis and also cleavability test for DCGS. The γ and CMC for DCGS were 36.8 (～50% γ H2O) and 1.62 × 10?5 mol L?1 and lower than simple GSs. The catalytic performance of DCGS was evaluated in the synthesis of aminocyanopyridines by the four-component reaction of acetophenone, malononitrile, (NH4)2CO3, and aldehydes in water. Thermal stability, easy separation and highest ever reported turnover number (TON) and turnover frequency (TOF) for synthesis of products are advantages of DCCGS.

Poly N,N-dimethylaniline-formaldehyde supported on silica-coated magnetic nanoparticles: a novel and retrievable catalyst for green synthesis of 2-amino-3-cyanopyridines

Preparation and application of novel and reusable magnetic nanoparticles with poly N,N-dimethylaniline-formaldehyde support as a heterogeneous basic catalyst have been described. The reported catalyst was characterized by Fourier transform infrared spectr

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.].