Malononitrile

Distribution by Scientific Domains
Distribution within Chemistry


Selected Abstracts


Selenium-Containing Heterocycles from Isoselenocyanates: 4-Methylselenazole Derivatives from the Reaction with Malononitrile and Propargyl Chloride

HELVETICA CHIMICA ACTA, Issue 2 2008
Geoffroy
Abstract Aryl isoselenocyanates 1 react with malononitrile (6a) and propargyl chloride (8) in DMF in the presence of Et3N to give the corresponding 2-(3-aryl-2,3-dihydro-4-methyl-1,3-selenazol-2-ylidene)malononitriles 12 as major products. The analogous reaction takes place with benzoylacetonitrile (6f) instead of 6a. In some cases, the corresponding noncyclic 2-[(arylamino)(prop-2-ynylselanyl)methylidene]malononitriles 9 were obtained as minor products. The structures of 9e and 11a have been established by X-ray crystallography. [source]


Selenium-Containing Heterocycles from Isoselenocyanates: Base-Catalyzed Reaction of Malononitrile with Phenyl Isoselenocyanate and Bromoacetonitrile or , -Halogenated Ketones

HELVETICA CHIMICA ACTA, Issue 10 2007
Geoffroy
Abstract The reaction of phenyl isoselenocyanate (1a) with malononitrile (=propanedinitrile) in DMF in the presence of Et3N leads to the intermediate ketene N,Se-hemiacetal 6a, which can be trapped with bromoacetonitrile or , -halogenated ketones 12a and 12b (Scheme,3). The products are [(alkylseleno)(phenylamino)methylene]malononitriles 10 and 13, which are obtained in good yield. In the case of the (2-oxoalkyl)seleno derivatives 13, they are in equilibrium with the cyclic hemiacetals 14. Chemical and spectroscopic evidence for the structures of the new compounds are described. The structure of 14a was established by X-ray crystallography. [source]


Back to Natural Cinchona Alkaloids: Highly Enantioselective Michael Addition of Malononitrile to Enones

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 18 2009
Alessio Russo
Abstract An efficient and convenient highly enantioselective Michael addition of malononitrile to enones has been developed by using quinine as the organocatalyst. The adducts were isolated in excellent yield and high asymmetric induction (up to 95% ee). An easy route to difficultly accessible ester derivatives has been also disclosed. [source]


Some novel accelerating agents for nitroxide-mediated living free-radical polymerization

JOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 21 2005
Huang Jianying
Abstract Malononitrile (MN), trifluoroacetic acid anhydride, acetylacetone, acetoacetic ester, and diethyl malonate have been identified as novel rate-accelerating additives for nitroxide-mediated living free-radical polymerization. Among these additives, MN has the greatest accelerating effect. Adding MN at an MN/2,2,6,6-tetramethylpiperidine-oxyl (TEMPO) molar ratio of 4.0 results in a nearly 20 times higher rate of polymerization of styrene (St), and adding MN at an MN/TEMPO molar ratio of 2.5 results in a nearly 15 times higher rate of copolymerization of St and methyl methacrylate. The polymerization of St proceeds in a living fashion, as indicated by the increase in the molecular weight with time and conversion and the relatively low polydispersity. The polymerization rate of St is so quick that the conversion reaches 70% within 1 h at 125 °C when the molar ratio of MN to TEMPO is 4:1. Moreover, the reaction temperature can be reduced to 110 °C. A possible explanation for this effect is that the formation of hydrogen bonds between the MN and TEMPO moiety weakens the CON bond at the end of the polymer chain. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 5246,5256, 2005 [source]


ChemInform Abstract: Electrocatalytic Multicomponent Cyclization of Aromatic Aldehydes, Malononitrile, and Malonates into 3-Substituted 2,2-Dicyanocyclopropane-1,1-dicarboxylates.

CHEMINFORM, Issue 37 2010
A. N. Vereshchagin
Abstract The first examples of a direct electrocatalytic multicomponent construction of the cyclopropane ring are given (16 examples). [source]


ChemInform Abstract: One-Pot Cascade Assembling of 3-Substituted Tetracyanocyclopropanes from Alkylidenemalononitriles and Malononitrile by the only Bromine Direct Action.

CHEMINFORM, Issue 15 2010
Anatolii N. Vereshchagin
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


ChemInform Abstract: Enantioselective Michael Addition of Malononitrile to Chalcones Catalyzed by a Simple Quinine,Al(OiPr)3 Complex: A Simple Method for the Synthesis of a Chiral 4H-Pyran Derivative.

CHEMINFORM, Issue 51 2009
Jian Shi
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


ChemInform Abstract: Electrocatalytic Multicomponent Assembling of Isatins, 3-Methyl-2-pyrazolin-5-ones and Malononitrile: Facile and Convenient Way to Functionalized Spirocyclic [Indole-3,4,-pyrano[2,3-c]pyrazole] System.

CHEMINFORM, Issue 24 2009
Michail N. Elinson
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


ChemInform Abstract: A Novel and Green Method for the Synthesis of Indeno[2,1-c]pyridine Derivatives in Ionic Liquid Catalyzed by Malononitrile.

CHEMINFORM, Issue 39 2008
Xiang-Shan Wang
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


ChemInform Abstract: A New Strategy of the Chemical Route to the Cyclopropane Structure: Direct Transformation of Benzylidenemalononitriles and Malononitrile into 1,1,2,2-Tetracyanocyclopropanes.

CHEMINFORM, Issue 22 2008
Michail N. Elinson
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


ChemInform Abstract: Highly Enantioselective Michael Addition of Malononitrile to ,,,-Unsaturated Ketones.

CHEMINFORM, Issue 21 2008
Xuefeng Li
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reaction of Malononitrile with Aldehydes and Thiols.

CHEMINFORM, Issue 36 2007
Nikolai M. Evdokimov
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]


Reaction of Heterocyclic Ketene Aminals with Bis(methylthio)methylene Malononitrile: Synthesis of Polyfunctionalized Pyridine-Fused 1,3-Diazaheterocycles from Heterocyclic Ketene Aminals.

CHEMINFORM, Issue 30 2007
Jiang-Peng Liao
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]


Phosphine-Catalyzed One-Pot Synthesis of Cyclopentenes from Electron-Deficient Allene, Malononitrile and Aromatic Aldehydes.

CHEMINFORM, Issue 21 2006
Xiyan Lu
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]


A Convenient One-Pot Synthesis of Substituted 1,1-Dicyanocyclopropanes from Sulfonium Salts, Malononitrile, and Carbonyl Compounds.

CHEMINFORM, Issue 15 2004
Aleksandr Shestopalov
Abstract For Abstract see ChemInform Abstract in Full Text. [source]


Highly Enantioselective Michael Addition of Malononitrile to Vinylogous Imine Intermediates Generated in situ from Arylsulfonyl Indoles

CHEMISTRY - A EUROPEAN JOURNAL, Issue 36 2010
Linhai Jing
Malononitrile on rare form: Highly enantioselective Michael addition of malononitrile to vinylogous imine intermediates 2, generated in situ from arylsulfonyl indoles 1, is described (see scheme). This protocol provides easy and convenient access to valuable 3-indolyl derivatives 3 in high yields and enantioselectivities. A possible catalytic mechanism is proposed. [source]


Michael-Addition Reaction of Malononitrile with ,,,-Unsaturated Cycloketones Catalyzed by KF/Al2O3

CHINESE JOURNAL OF CHEMISTRY, Issue 2 2004
Xiang-Shan Wang
Abstract A series of KF/Al2O3 catalyzed Michael-addition reactions between malononitrile and ,,,-unsaturate cycloketones in DMF solution were studied. At room temperature, 2-cyano-3-aryl-3,(1, 2, 3, 4-tetrahydronaphthalen-1-one-2-yl) propionitrile derivatives were synthesized by the reaction between 2-arylmethylidene-1, 2, 3, 4-tetra-hydronaphthalen-l-one and malononitrile. However, if the temperature was increased to 80 C, 2-amino-3-cyano-4-aryl-4H -benzo[h]chromene derivatives were obtained in high yields. When the ,,,-unsaturated ketones were replaced by 2, 6-biarylmethylidenecyclohexanone or 25-biarylmethylidenecyclopentanone, another series of 2-amino-3-cyano-4H -pyran derivatives was isolated successfully. The structures of the products were confirmed by X-ray diffraction analysis. [source]


Selenium-Containing Heterocycles from Isoselenocyanates: 4-Methylselenazole Derivatives from the Reaction with Malononitrile and Propargyl Chloride

HELVETICA CHIMICA ACTA, Issue 2 2008
Geoffroy
Abstract Aryl isoselenocyanates 1 react with malononitrile (6a) and propargyl chloride (8) in DMF in the presence of Et3N to give the corresponding 2-(3-aryl-2,3-dihydro-4-methyl-1,3-selenazol-2-ylidene)malononitriles 12 as major products. The analogous reaction takes place with benzoylacetonitrile (6f) instead of 6a. In some cases, the corresponding noncyclic 2-[(arylamino)(prop-2-ynylselanyl)methylidene]malononitriles 9 were obtained as minor products. The structures of 9e and 11a have been established by X-ray crystallography. [source]


Selenium-Containing Heterocycles from Isoselenocyanates: Base-Catalyzed Reaction of Malononitrile with Phenyl Isoselenocyanate and Bromoacetonitrile or , -Halogenated Ketones

HELVETICA CHIMICA ACTA, Issue 10 2007
Geoffroy
Abstract The reaction of phenyl isoselenocyanate (1a) with malononitrile (=propanedinitrile) in DMF in the presence of Et3N leads to the intermediate ketene N,Se-hemiacetal 6a, which can be trapped with bromoacetonitrile or , -halogenated ketones 12a and 12b (Scheme,3). The products are [(alkylseleno)(phenylamino)methylene]malononitriles 10 and 13, which are obtained in good yield. In the case of the (2-oxoalkyl)seleno derivatives 13, they are in equilibrium with the cyclic hemiacetals 14. Chemical and spectroscopic evidence for the structures of the new compounds are described. The structure of 14a was established by X-ray crystallography. [source]


Benzofuranyl-pyran-2-ones, -pyridazines, and -pyridones from naturally occurring furochromones (visnagin and khellin)

HETEROATOM CHEMISTRY, Issue 1 2004
Eman M. Keshk
The novel and versatile enaminones 2a,b were synthesized by treatment of visnaginone methyl ether 1a or khellinone methyl ether 1b with N,N -dimethylformamide dimethylacetal. They were reacted with hippuric acid or N -acetylglycine to yield benzofuran-5-yl-2H-pyran-2-ones 3a,d. The reaction of 2a,b with cyanoacetamide and malononitrile dimer in sodium ethoxide gave benzofuran-5-yl-pyridones 4a,b and [benzofuran-5-yl-1H-pyridine-2-ylidene] malononitrile 5a, respectively. Refluxing 2a,b with hydrazine hydrate or with hydroxyla- mine afforded benzofuran-5-yl-1H-pyrazoles 6a,b and benzofuran-5-yl-isoxazoles 7a,b, respectively. Moreover, 2a,b coupled with aryl diazonium salt in the presence of sodium hydroxide to yield 3-(benzofuran-5-yl)-2-aryl-hydrazono-3-oxo-propanals 8a,b which were excellent precursors for the synthesis of pyridazines 9,12. © 2003 Wiley Periodicals, Inc. 15:85,91, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10219 [source]


One-pot PTC synthesis of polyfused pyrazoles

HETEROATOM CHEMISTRY, Issue 3 2003
Gamal A. El-Saraf
Thienopyrazole 2, 3, 5, or 6 and thienopyrazolothiazepine 7, 9, and 11 derivatives were prepared via the reaction of the 3-aminopyrazoline-5-one 1 with CS2 and different molar ratio of a variety of halo compounds having an active methylene under PTC conditions. Also, treatment of 1 with CS2 and alcoholic KOH in 2:1:1 molar ratio afforded dipyrazolopyridine derivatives 12 and 14. On other hand, the pyrazolothiadiazineone derivative 13 was obtained by treating compound 1 with CS2 and alcoholic KOH in 1:2:2 molar ratio. Under PTC conditions, compound 1, CS2, and ethyl cyanoacetate or malononitrile to gave the pyrazolopyridine derivatives 16 and 17. Coupling of compound 1 with diazonium acetates afforded the hydrazone derivatives 18a,b, which were oxidized with bromine to give pyrazolotriazoles 19a,b or cyclized with aldehydes to give pyrazolotriazine derivatives 20a,e. Bromination of compound 1 afforded monobromopyrazole derivative 21, which could be condensed to a dipyrazolopyrazindione 23. Finally, the dibromopyrazole derivative 22 was cyclized with 2-mercaptoethanol or o-phenylenediamine to give the spiropyrazoles 24a,b. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:211,217, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10129 [source]


Theoretical study on the mechanism of reaction between 3-hydroxy-3-methyl-2-butanone and malononitrile catalyzed by magnesium ethoxide

INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, Issue 4 2009
Lin-Sen Heng
The mechanism of reaction between 3-hydroxy-3-methyl-2-butanone and malononitrile for the synthesis of 2-dicyanomethylene-4,5,5-trimethyl-2,5-dihydrofuran-3-carbonitrile catalyzed by magnesium ethoxide was investigated by density functional theory (DFT). The geometries and the frequencies of reactants, intermediates, transition states, and products were calculated at the B3LYP/6,31G(d) level. The vibration analysis and the IRC analysis demonstrated the authenticity of transition states, and the reaction processes were confirmed by the changes of charge density at bond-forming critical point. The results indicated that magnesium ethoxide is an effective catalyst in the synthesis of 2-dicyanomethylene-4,5,5-trimethyl-2,5-dihydrofuran-3-carbonitrile from malononitrile and 3-hydroxy-3-methyl-2-butanone. The activation energy of reaction with magnesium ethoxide decreased by 102.37 kJ mol,1 compared with that of the reaction without it. The mechanism of reaction with catalyst magnesium ethoxide differs from that of reaction without it. © 2008 Wiley Periodicals, Inc. Int J Chem Kinet 41: 227,235, 2009 [source]


A Simple Copper-Catalyzed Cascade Synthesis of 2-Amino-1H -indole-3-carboxylate Derivatives

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 6 2010
Xiaobo Yang
Abstract We have developed a simple and efficient copper-catalyzed method for the synthesis of 2-amino-1H -indole-3-carboxylate derivatives via cascade reactions of substituted N -(2-halophenyl)-2,2,2-trifluoroacetamide with alkyl 2-cyanoacetate or malononitrile under mild conditions, and the method is of wide practical application. [source]


Back to Natural Cinchona Alkaloids: Highly Enantioselective Michael Addition of Malononitrile to Enones

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 18 2009
Alessio Russo
Abstract An efficient and convenient highly enantioselective Michael addition of malononitrile to enones has been developed by using quinine as the organocatalyst. The adducts were isolated in excellent yield and high asymmetric induction (up to 95% ee). An easy route to difficultly accessible ester derivatives has been also disclosed. [source]


Efficient Method for the Synthesis of Optically Active 2-Amino-2-chromene Derivatives via One-Pot Tandem Reactions

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 18 2009
Jian-Wu Xie
Abstract The asymmetric synthesis of functionalized 2-amino-2-chromene derivatives with high enantioselectivities via one-pot tandem reactions of functionalized ,,,-unsaturated ketones with malononitrile catalyzed by 9-amino-9-deoxyepiquinine (1a) in combination with (R)-1,1,-binaphth-2,2,-diyl hydrogen phosphate (1c) is reported for the first time. [source]


Ruthenium Catalysts for Controlled Mono- and Bis-Allylation of Active Methylene Compounds with Aliphatic Allylic Substrates

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 16 2009
Hui-Jun Zhang
Abstract The allylation of 1,3-dicarbonyl compounds and malononitrile with aliphatic allylic substrates is achieved under mild conditions in the presence of new ruthenium catalysts. The ruthenium complex [Ru(C5Me5)(2-quinolinecarboxylato)(CH2CHCH- n -Pr)],[BF4] as a precatalyst, allows the synthesis of mono-allylated branched derivatives. On the other hand, the parent complex [Ru(C5Me5)(MeCN)3],[PF6] as a precatalyst, straightforwardly favours the bis-allylation of the procarbonucleophiles leading to bis-allylated bis-linear products. The involvement of the two precatalysts provides a sequential synthesis of unsymmetrical mixed linear-branched bis-allylated derivatives. [source]


Riot control agents: pharmacology, toxicology, biochemistry and chemistry,

JOURNAL OF APPLIED TOXICOLOGY, Issue 5 2001
Eugene J. Olajos
Abstract The desired effect of all riot control agents is the temporary disablement of individuals by way of intense irritation of the mucous membranes and skin. Generally, riot control agents can produce acute site-specific toxicity where sensory irritation occurs. Early riot control agents, namely, chloroacetophenone (CN) and chlorodihydrophenarsazine (DM), have been replaced with ,safer' agents such as o -chlorobenzylidene malononitrile (CS) and oleoresin of capsicum (OC). Riot control agents are safe when used as intended: however, the widespread use of riot control agents raises questions and concerns regarding their health effects and safety. A large margin exists between dosages that produce harassment and dosages likely to cause adverse health effects for modern riot control agents such as CS and dibenz[b,f]1 : 4-oxazepine (CR). Yet, despite the low toxicity of modern riot control agents, these compounds are not entirely without risk. The risk of toxicity increases with higher exposure levels and prolonged exposure durations. Ocular, pulmonary and dermal injury may occur on exposure to high levels of these substances, and exposure to riot control agents in enclosed spaces may produce significant toxic effects. Reported deaths are few involving riot control agents, and then only under conditions of prolonged exposure and high concentrations. Recently, concern has focused on the deaths resulting from law enforcement use of OC, a riot control agent generally regarded as safe because it is a natural product. As with other xenobiotics, not enough is known concerning the long-term/chronic effects of riot control agents. Clearly, there is considerable need for additional research to define and delineate the biological and toxicological actions of riot control agents and to illuminate the full health consequences of these compounds as riot control agents. Copyright © 2001 John Wiley & Sons, Ltd. [source]


Selectivity of N -aroyl- N,-arylthioureas towards 2-(1,3-dioxo-1H -inden-2(3H)-ylidene)malononitrile.

JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 3 2010
2- d][, 3]- thiazepin-2(6H)-ylidene)-4-arylamides of antitumor, New synthesis of (Z)- N -((E)-4-amino-1-aryl-5-cyano-6-oxo-1H -indeno[, antioxidant activities
The reaction between N -aroyl- N,-arylthioureas with 2-(1,3-dioxoindan-2-ylidene)malononitrile furnished indeno[1,2- d][1,3]thiazepines in 70,85% yields. The mechanism of the products' formation is discussed. Some of the products showed effective antitumor and antioxidant activities. The results revealed that compound indenothiazepine derivative showed a high inhibition of the cell growth of Hep-G2 cells is compared with the growth of untreated control cells, as concluded from their low IC50 value 21.73 ,M. On the other hand, two indenothiazepine derivatives have an effective antioxidant activity with SC50 values of 62.5 mM and 87.4 mM, respectively. J. Heterocyclic Chem., (2010). [source]


Facile, efficient, and eco-friendly synthesis of benzo[b]pyran-2-imines over MgO and transformation to the coumarin derivatives

JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 6 2009
Hassan Valizadeh
Room temperature synthesis of benzo[b]pyran-2-imine derivatives via the Knoevenagel condensation of malononitrile and cyanoacetates with salicylaldehyde derivatives over MgO and their transformation to the known coumarins is described. The satisfactory results were obtained with good yields, short reaction time, and simplicity in the experimental procedure. J. Heterocyclic Chem., (2009). [source]


An efficient method for synthesis of pyrano[3,2- c]pyridine derivatives under microwave irradiation

JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 5 2009
Shu-Liang Wang
A series of pyrano[3,2- c]pyridine derivatives were synthesized via reactions of 3,5-dibenzylidene-piperidin-4-one and malononitrile in N,N -dimethylformamide under microwave irradiation. It is a simple, efficient, and promising synthetic method to construct pyrano[3,2- c]pyridine skeleton. J. Heterocyclic Chem., (2009). [source]