2232-13-5

Upstream product

• 16135-31-2 p-nitroformanilide 
• 3861-18-5 N-(4-nitro-phenyl)-N'-phenyl-formamidine 
• 128799-78-0 N¹-(p-chlorobenzoyl)-N¹,N²-di(p-nitrophenyl)formamidine 
• 130340-58-8 N,N-bis(p-nitrophenyliminomethyl)-p-nitroaniline 
• 64-19-7 acetic acid 
• 100-01-6 4-nitro-aniline 
• 122-51-0 orthoformic acid triethyl ester 
• 762-04-9 phosphonic acid diethyl ester 
• 40412-00-8 ethyl N-(p-nitrophenyl)formimidate 
• 128799-78-0 N¹-(p-Chlorobenzoyl)-N¹,N²-di(p-nitrophenyl)formamidine 

Downstream Products

• 68538-05-6 5-methyl-4-(4-nitro-anilinomethylene)-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 91975-03-0 4-Nitro-3-methyl-5-<2-(4-nitro-anilino)-vinyl>-isoxazol 
• 128915-06-0 N¹⁶-(3,5-dichlorobenzoyl)-N¹,N²-di(p-nitrophenyl)formamidine 
• 2416-53-7 N-(p-Nitrophenyl)-N'-methylformamidin 
• 128915-10-6 N¹-(p-methylbenzyl)-N²-(p-nitrophenyl)formamidine 
• 1198228-91-9 diethyl bis(p-nitrophenylamino)methanephosphonate 
• 41078-59-5 N-(4-Nitro-phenyl)-N-[2-(4-nitro-phenylamino)-ethyl]-formamide 
• 5431-36-7 NSC 13585 
• 133545-35-4 N,N'-bis(4-nitrophenyl)propane-1,3-diamine 
• 56225-07-1 1.4-Bis-(4-Nitroanilino)butan 
• 130340-63-5 N¹-(o-chlorobenzoyl)-N¹,N²-di-(p-nitrophenyl)formamidine 
• 58442-15-2 N,N'-bis-(4-amino-phenyl)-formamidine 
• 1160-42-5 N-[2-(3-methyl-3H-benzothiazol-2-ylidene)-ethylidene]-4-nitro-aniline 
• 1160-41-4 N-[2-(3-methyl-3H-benzooxazol-2-ylidene)-ethylidene]-4-nitro-aniline 

Relevant academic research and scientific papers

Preparation of Fe3O4@C-dots as a recyclable magnetic nanocatalyst using Elaeagnus angustifolia and its application for the green synthesis of formamidines

This work describes a novel and simple procedure for successfully synthesizing formamidines by using Fe3O4@C-dots in the role of an effective and reusable catalyst throughout a solvent-free set-up. The formamidine derivatives were easily prepared through aromatic amines with triethyl orthoformate in the company of Fe3O4@C-dots. According to the experimental outcomes, the obtained formamidines in the presence of Fe3O4@C-dots exhibited good to high yield values. In the following, we distinguished the prepared catalyst by applying field emission scanning electron microscope (FESEM), transmission electron microscopy (TEM), energy-dispersive X-ray (EDX), X-ray diffraction (XRD), Fourier transform infrared (FTIR), and vibrating sample magnetometer (VSM) techniques. Furthermore, the evaluation of catalytic activity was done in the course of synthesizing formamidine derivatives. Among the advantages of this method, one can highlight the facts of solvent-free conditions, the simplicity of operation, high yields, nonacidic catalyst, and the reusability of nanocatalyst for at least five cycles.

Catalyst-Free Synthesis of Aryl Diamines via a Three-Step Reaction Process

The formation of C-N bonds with aryl amines is one of the most widely studied reactions in organic chemistry. Despite this, it is still highly challenging, often requiring expensive, precious metal-based catalysts. Here we report an easy catalyst-free methodology for constructing C-N bonds. The method, which proceeds via the in situ formation of closed ring amidinium ions, allows the preparation of a series of symmetrical and/or unsymmetrical aryl diamines in notably high yields (82-98%) and purity and with a variety of different substituents. The methodology is shown successful for the preparation of aryl diamines having para- and/or meta-substituted carboxyl, nitro, bromo, methoxy, or methyl groups. This green synthetic pathway, which is catalyst free, requires only three steps, and proceeds without the need for purification. Further, it is a new sustainable, economically viable method to achieve an otherwise challenging bond formation.

Ionic liquid-functionalized mesoporous silica nanoparticles ([pmim]FeCl4/MSNs): Efficient nanocatalyst for solvent-free synthesis of N,N′-diaryl-substituted formamidines

We report the synthesis of ionic liquid-functionalized mesoporous silica nanoparticles ([pmim]FeCl4/MSNs) via a method of post-grafting on parent MSNs. This hybrid material was characterized using scanning and transmission electron microscopies, energy-dispersive X-ray spectroscopy, nitrogen adsorption–desorption analysis, Fourier transform infrared spectroscopy, powder X-ray diffraction and thermal analyses. The material was utilized as an efficient heterogeneous catalyst for the synthesis of N,N′-diaryl-substituted formamidines through the reaction of triethyl orthoformate with arylamines under solvent-free conditions. The catalyst was recovered easily and reused several times without significant loss of its catalytic activity.

Ultrasound promoted expeditious, catalyst-free and solvent-free approach for the synthesis of N,N′-diarylsubstituted formamidines at room temperature

An effortless and efficient protocol was developed for the synthesis of N,N′-diarylsubstituted formamidines under environment-friendly conditions. Ultrasonic energy was employed to obtain the desired products in excellent yields with high purity under solvent-free and catalyst-free conditions. Products were purified by the crystallization technique to avoid excess utilization of organic solvents.

Insight into the mechanism of three component condensation leading to aminomethylenebisphosphonates

Three-component reaction of a primary amine, diethyl phosphite and triethyl orthoformate followed by acid hydrolysis of the adduct provides N-substituted aminomethylenebisphosphonic acids in good yields. Being extremely versatile, it is commonly utilized for preparation of compounds possessing potential antiosteoporotic, antibacterial, anticancer, antiparasitic or herbicidal activity. However, the mechanism of the reaction remains unknown. p-Nitroaniline has been found an interesting tool to shed light on this matter. Its use allowed to separate and identify four intermediates, both non-phosphorus and phosphorus containing, and subsequently suggest the mechanism of the whole process. The acquired knowledge was helpful in explanation the route and the final product structure obtained for more complex reaction proceeding with the use of 4-aminopyridine. Additional alkylation of the pyridine nitrogen atom, leading to unexpected N-(1-alkylpyridinium-4-amino)methylenebisphosphonic acids was unambiguously proved.

Amidines. I. Hydrolysis of N1-acyl- and N1-tosyl-N1,N2-diarylamidines

In acid hydrolysis of N1-acyl-N1,N2-diarylamidines, a water molecule attacked exclusively the amidine central carbon, and the reaction proceeded in parallel through two pathways. One of them leads to the formation of two N-acylarylamines, and the other leads to the formation of N,N-diacylarylamine and arylamine. Acid hydrolysis of N1-tosyl-N1,N2-diarylamidine was also examined. The results were similar to those of the hydrolysis of N1-acyl-N1,N2-diarylamidines. Alkaline hydrolysis and alcoholysis of N1-acyl-N1,N2-diarylamidines occurred almost exclusively at the amide carbonyl group to give N1,N2-diarylamidines and carboxylic acids or their esters. The effects of structural change and the aryl substituents on the rate and direction of the reaction were examined.