1202-48-8

Usage

Physical state

Bright yellow solid

Common uses

Organic synthesis, chemical research

Functional groups

Aniline group, malononitrile group

Known for

Reactivity in various reactions

Usage

Precursor for the synthesis of various organic compounds (e.g. pharmaceuticals, dyes, specialty chemicals)

Field of study

Organic chemistry

InChI:InChI=1/C10H7N3/c11-6-9(7-12)8-13-10-4-2-1-3-5-10/h1-5,8,13H

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 109-77-3 malononitrile 
• 62-53-3 aniline 
• 123-06-8 Ethoxymethylenemalononitrile 
• 997-76-2 tricyanoethene 
• 1783-25-1 N₁,N₁-dimethyl-N₂-phenylformamidine 
• 80420-96-8 α-Cyano-β-anilinoacrylamide 
• 149-73-5 trimethyl orthoformate 
• 91255-20-8 N,N-Dimethyl-N'-(α-cyano-β-N'-anilinoacrylyl)formamidine 

Downstream Products

• 1439-67-4 2-[5-(Triphenyl-λ⁵-phosphanylidene)-cyclopenta-1,3-dienylmethylene]-malononitrile 
• 112124-35-3 sodium 6-amino-3,5-dicyanopyridine-2-thiolate 
• 59021-52-2 [(2,2-Dicyano-vinyl)-phenyl-amino]-acetic acid ethyl ester 
• 130224-42-9 5-amino-3-(phenylamino)-1H-pyrazole-4-carbonitrile 
• 165267-30-1 N-ethoxycarbonylanilinomethylenemalononitrile 
• 59021-51-1 ethyl 3-amino-4-cyano-1-phenyl-1H-pyrrole-2-carboxylate 
• 59021-49-7 4-amino-5-benzoyl-1-phenyl-pyrrol-3-carbonitril 
• 88796-36-5 4-amino-1-phenyl-pyrrol-3-carboxamid 
• 145162-46-5 4-amino-1-phenyl-pyrrol-3-carbonitril 
• 60531-49-9 N-(2,2-dicyanovinyl)-N-benzyl-3,5-bistrifluoromethyl-aniline 
• 52832-04-9 N-(trichloromethylthio)anilinomethylenemalononitrile 
• 83907-79-3 3-amino-1-phenyl-1H-pyrrole-2,4-dicarbonitrile 
• 889997-32-4 5-acetyl-4-amino-1-phenyl-1H-pyrrole-3-carbonitrile 

Relevant academic research and scientific papers

Solvent-free synthesis of quinolone derivatives

Quinolones can be prepared in a three step procedure from triethylorthoformate and activated methylene derivatives leading to alkoxymethylenemalonates followed by reaction with aromatic amines and finally a cyclization. All the reactions were carried out under solvent-free conditions possibly under microwave activation with benefits for the first step.

1,1'-Dicyano-2-substituted ethylenes : A new class of glucose uptake inhibitors in antifilarial chemotherapy

Several 1,1'-dicyano-2-substituted ethylenes (2-16) were synthesized and evaluated for in vivo antifilarial activity. Some of the screened compounds showed significant antifilarial response against Acanthocheilonema viteae in rodents.

One Pot Synthesis of 3-Amino-1H-pyrazole-4-carbonitrile

Condensation of malodinitrile with trimethoxymethan and aniline affords 3-anilino-2-cyanoacrylonitrile, which on treatment with hydrazine gives the title compound.Aniline can be recovered almost quantitatively. Keywords: Enaminonitrile; Amine exchange; Cyclisation

An efficient synthesis of 3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one derivatives via an iminophosphorane

The iminophosphorane (3), obtained from reaction of ethyl 3-amino-4-cyano-1-phenyl-1H-pyrrole-2-carboxylate (2) with triphenylphosphine, hexachloroethane, and triethylamine, reacted with aromatic isocyanates to give carbodiimides (4). Further reaction of

Triflic acid-mediated N-heteroannulation of β-anilino-β-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines

Various functionalised 4-amino-2-(methylthio)quinolines are synthesised through triflic acid-mediated N-heteroannulation of α-functionalized-β-anilino-β-(methylthio)acrylonitriles for the first time. The N-heteroannulation process is highly chemoselective and has mild reaction conditions. However, this process fails in the absence of the β-methylthio group in the acrylonitriles. In addition, a new double N-heteroannulation process is demonstrated to synthesise indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine is synthesised in four steps from an acyclic precursor.

Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.

Pyrrolopyrimidine derivatives and purine analogs as novel activators of Multidrug Resistance-associated Protein 1 (MRP1, ABCC1)

Multidrug resistance (MDR) is the main cause of diminished success in cancer chemotherapy. ABC transport proteins are considered to be one important factor of MDR. Besides P-glycoprotein (P-gp, ABCB1) and Breast Cancer Resistance Protein (BCRP, ABCG2), Mu

Synthesis and biological evaluation of new tacrine analogues under microwave irradiation

Efficient routes to various kinds of heterocycles incorporating the p-halophenyl moiety have been synthesized. Different pyrrole derivatives have been synthesized, as well, by Thorpe–Ziegler cyclization. Therefore, we synthesized different analogues of tacrine by Friedl?nder reaction of o-amino nitriles (pyrazolo, furano and pyrrolo) with different cycloalkanones. The use of microwave irradiation leads to shorter production times and high product conversion. These synthesized compounds were biologically evaluated by Ellman’s test on acetylcholinesterase inhibition.

Pyrrolopyrimidine Derivatives as Novel Inhibitors of Multidrug Resistance-Associated Protein 1 (MRP1, ABCC1)

Five series of pyrrolo[3,2-d]pyrimidines were synthesized and evaluated with respect to potency and selectivity toward multidrug resistance-associated protein 1 (MRP1, ABCC1). This transport protein is a major target to overcome multidrug resistance in cancer patients. We investigated differently substituted pyrrolopyrimidines using the doxorubicin selected and MRP1 overexpressing small cell lung cancer cell line H69 AR in a calcein AM and daunorubicin cell accumulation assay. New compounds with high potency and selectivity were identified. Piperazine residues at position 4 bearing large phenylalkyl side chains proved to be beneficial for MRP1 inhibition. Its replacement by an amino group led to decreased activity. Aliphatic and aliphatic-aromatic variations at position 5 and 6 revealed compounds with IC50 values in high nanomolar range. All investigated compounds had low affinity toward P-glycoprotein (P-gp, ABCB1). Pyrrolopyrimidines with small substituents showed moderate inhibition against breast cancer resistance protein (BCRP, ABCG2).

Oxidation of 2-cyanoprop-2-enethioamides with hydrogen peroxide

Oxidation of (E)-3-aryl-2-cyanoprop-2-enethioamides with 32% H 2O2 under mild conditions gave (E)-3-aryl-2-cyano-1- iminioprop-2-ene-1-sulfenates in 70-88% yields. Under the conditions of the Radziszewski reaction (H2O2, 10% aqueous KOH) or upon prolonged treatment with H2O2, (E)-3-aryl-2-cyanoprop-2- enethioamides underwent transformations leading to complex mixtures of oxidation products. In some cases, 3-aryloxirane-2,2-dicarboxamides were isolated from those mixtures in low yields (2O2/KOH in ethanol afforded (arylaminomethylidene)malononitriles.