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A facile synthesis of ( 15 N 2 ) malononitrile - DeepDyve

Freeman, F. 2001. Malononitrile. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

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Malononitrile for synthesis | VWR

2,5-hexanedione) react with malononitrile in benzene in the presence of ammonium acetate or piperidinium acetate to give an array of products including double Knoevenagel adducts, cyclopentadiene derivatives, and 1-pyrindine derivatives (eq 7).Ethyl pyruvate condenses with malononitrile to yield ethyl 2-dicyanomethylenepropanoate (eq 8), a useful dienophile in the Diels-Alder reaction and in natural products synthesis., Ethoxycarbonyl-1-cyclohexanone reacts with malononitrile to give the Knoevenagel condensation product, which rearranges to the tetrahydroisoquinoline (eq 9).,,The Knoevenagel reaction of aliphatic methyl ketones with malononitrile produces 6-alkyl-2,4-diamino-3,5-dicyanopyridines in moderate yield. The Michael reaction between aliphatic ,-unsaturated ketones and malononitrile gives 2-amino-3-cyano-4,6-dialkylpyridines. Conjugated aromatic ketones react with malononitrile in the presence of ammonium acetate to give 2-amino-4,6-diarylnicotinonitriles. The Michael addition of malononitrile to -acetylcinnamamides and chiral -acylacrylates to form 2-amino-4-pyrans and polyfunctionalized carbocycles,, and the first asymmetric synthesis of polyfunctionalized 4-pyrans via Michael addition of malononitrile to 2-acyl acrylates, have been reported. Polyfunctionalized 4-pyrans are a common structural unit in a number of natural products.

Synthesis of O -Heterocycles - Organic Chemistry Portal

Malononitrile reacts with carbon disulfide in aqueous ammonia to yield 4,6-diamino-3,5-dicyano-2-1-thiapyran-2-thione (eq 13). Malononitrile reacts with carbon disulfide and sulfur in the presence of secondary or tertiary amines to give 4-cyano-5-amino-1,2-dithiole-3-thione. 2-Amino-3-cyano-4,5-dialkylthiophenes are obtained from malononitrile, ketones, and sulfur. Cholestan-3-one reacts with malononitrile and sulfur in ethanol containing morpholine to produce cholestanothiophene (2�-aminocholest-2-eno[3,2-]thiophene-4�-carbonitrile) (eq 14).Malononitrile forms synthetically useful dimers and trimers and can be alkylated under a variety of experimental conditions., Ethyl orthoformate reacts with malononitrile to form . Malononitrile reacts with 2,3-bis(phenylsulfonyl)-1,3-butadiene via a novel 4-annulation to yield 1-sulfonyl-4,4-dicyanocyclopentene. Cholest-1-en-3-yl esters undergo allylic alkylation with malononitrile in the presence of a palladium catalyst. Malononitrile may be used to prepare adenine,, aminopyrroles, aminocyanopyrroles, diaminopyrimidines, and many other heterocycles. Malononitrile is converted to aminomalononitrile (aminopropanedinitrile) which is useful in the synthesis of heterocycles including pyrazines,, -nucleosides,,

Pyridine synthesis - Organic chemistry

Synthesis of Polysubstituted Dihydropyridines by Four-Component Reactions of Aromatic Aldehydes, Malononitrile, Arylamines, and Acetylenedicarboxylate

Effective catalysts for the condensation include glycine and -alanine., Benzaldehyde condenses with malononitrile in the presence of a catalytic amount of glycine to give benzalmalononitrile, which is valuable in heterocyclic synthesis, in quantitative yield (eq 1). The condensation of 1,4-cyclohexanedione with malononitrile proceeds almost quantitatively to 1,4-bis(dicyanomethylene)cyclohexane under catalysis by -alanine (eq 2). 1,4-Bis(dicyanomethylene)cyclohexane is used to prepare the quinomethane electron acceptor 7,7,8,8-tetracyanoquinonedimethane (TCNQ). In general, the Knoevenagel condensation of malononitrile with ketones or esters is efficiently catalyzed by weak bases

N-substituted pyrido[4,3-d]pyrimidines are heterocycles which exhibit the asymmetric hydrogen bonding codes of both guanine and cytosine at 60 angles to each other, such that the molecules self-organize unambiguously into a cyclic hexamer, assembled via 18 intermolecular hydrogen bonds. The synthesis is straightforward and can be concluded in six steps from the commercially available malononitrile dimer. X-ray crystallographic analysis of the supermacrocyclic structure shows an undulating disk with a ca. 10.5 Å cavity, the centers of which do not overlap sufficiently to describe a channel in the solid state. However, AFM, SEM, and TEM imaging in solution reveals the formation of 1D nanostructures in agreement with their self-assembly into rosette supermacrocycles, which then stack linearly to form rosette nanotubes.

Thieme E-Books & E-Journals - Synthesis / Issue

Synthesis and structural properties of 2-((10-alkyl-10H-phenothiazin-3-yl)methylene)malononitrile derivatives; a combined experimental and theoretical insight

AB - N-substituted pyrido[4,3-d]pyrimidines are heterocycles which exhibit the asymmetric hydrogen bonding codes of both guanine and cytosine at 60 angles to each other, such that the molecules self-organize unambiguously into a cyclic hexamer, assembled via 18 intermolecular hydrogen bonds. The synthesis is straightforward and can be concluded in six steps from the commercially available malononitrile dimer. X-ray crystallographic analysis of the supermacrocyclic structure shows an undulating disk with a ca. 10.5 Å cavity, the centers of which do not overlap sufficiently to describe a channel in the solid state. However, AFM, SEM, and TEM imaging in solution reveals the formation of 1D nanostructures in agreement with their self-assembly into rosette supermacrocycles, which then stack linearly to form rosette nanotubes.

N2 - N-substituted pyrido[4,3-d]pyrimidines are heterocycles which exhibit the asymmetric hydrogen bonding codes of both guanine and cytosine at 60 angles to each other, such that the molecules self-organize unambiguously into a cyclic hexamer, assembled via 18 intermolecular hydrogen bonds. The synthesis is straightforward and can be concluded in six steps from the commercially available malononitrile dimer. X-ray crystallographic analysis of the supermacrocyclic structure shows an undulating disk with a ca. 10.5 Å cavity, the centers of which do not overlap sufficiently to describe a channel in the solid state. However, AFM, SEM, and TEM imaging in solution reveals the formation of 1D nanostructures in agreement with their self-assembly into rosette supermacrocycles, which then stack linearly to form rosette nanotubes.

The Condensation of Salicylaldehydes and Malononitrile Revisited: Synthesis of New Dimeric Chromene Derivatives
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    How to Cite. Freeman, F. 2001. Malononitrile. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

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Malononitrile, 2-phenylazo- | C9H6N4 | ChemSpider

The reaction of salicylic aldehydes with malononitrile was reinvestigated, and the reaction pathway was followed by 1H NMR spectroscopy. A delicate control of the experimental conditions allowed the synthesis of 2-imino-2-chromene-3-carbonitriles 1, (2-amino-3-cyano-4-chromen-4-yl)malononitriles 2, 4-amino-5-imino-2,7-dimethoxy-5-chromeno[3,4-]pyridine-1-carbonitrile 12, and (4,5-diamino-1-cyano-1,10b-dihydro-2-chromeno[3,4-]pyridin-2-ylidene)malononitrile 13. Two novel 2-iminochromene dimers, with structures 8 and 9, were isolated and fully characterized. The activity of compound 8a on spp. growth and on ochratoxin A production was evaluated. The results of the bioassays indicate that compound 8a, applied at concentrations of 2 mM, totally inhibited the growth of the fungi tested. Ochratoxin A production by was reduced by about 93% with a 200 μM solution of this compound. A moderate inhibitory effect was observed for the analogous structure 8b, and no inhibition was registered for compounds 2 and 1, used as synthetic precursors of the dimeric species 8.

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