Potassium 1,1,3,3-Tetracyano-2-[2-(methoxycarbonyl)benzoyl]prop-2-enide in the Synthesis of Spiro-Fused Isobenzofuran Derivatives

Russian Journal of Organic Chemistry - Successive treatment of potassium 1,1,3,3-tetracyano-2-(2-(methoxycarbonyl)benzoyl)prop-2-enide with concentrated sulfuric acid and water gave...     

2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides

Reactions of 2-aroyl-1,1,3,3-tetracyanopropenides with hydrogen halides in solvents of low dielectric permittivity result in the formation of 6-amino-2-aroyl-2-halopyridine-3,5-dicarbonitriles. 2-Acyl-1,1,3,3-tetracyanopropenides under similar conditions afford 2-(2-alkylidene-5-amino-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles. In solvents of high dielectric permittivity the result of the reaction depends on the nature of the hydrogen halide and the acyl(aroyl) substituent: With HCl and HBr 2-aroyl-1,1,3,3-tetracyanopropenides form 2-(5-amino-2-aryl-2-halo-4-cyano-2,3-dihydrofuran-3-ylidene)-propanedinitriles, and 2-acyl-1,1,3,3-tetracyanopropenides give 2-(2-alkylidene-5-amino-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles; with HI depending on the reaction conditions and the structure of the acyl substituent 2-(5-amino-2-aryl-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles, 2-(5-amino-4-cyano-2,3-dihydrofuran-3-ylidene) propane-dinitrile, 2-amino-4-(dimethoxybenzyl)-6-iodo-5-cyanonicotinamide, 4-amino-6-iodo-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitrile, or 4-amino-6-iodo-3-oxo-1-ethylidene-1,3-dihydrofuro[3,4-c]pyridine-7-carbonitrile are obtained.     

2-acyl(aroyl)-1,1,3,3-tetracyanopropenides: V. Reaction with hydrazine hydrate

Reactions of 2-acyl(aroyl)-1,1,3,3-tetracyanopropenides with hydrazine hydrate followed by neutralization led to the formation of 2-amino-4-[hydrazono(aryl)methyl]-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles.     

Reaction of 3-(ethylamino)-2,2-dimethylpropanal with alkylene phosphites

Russian Journal of General Chemistry -     

11,11,12,12-四氰基-2-对甲基苯基-9,10-蒽醌二甲烷的合成及其光谱性能

以邻苯二甲酸酐和对溴甲苯为原料,经Friedel-Crafts酰基化、浓硫酸催化、Suzuki偶联及Knoevenagel缩合合成了一种新型的四氰基-9,10-蒽醌二甲烷衍生物——11,11,12,12-四氰基-2-对甲基苯基-9,10-蒽醌二甲烷(5),其结构经1H NMR,ESI-MS和元素分析表征。UV-Vis和荧光光谱研究表明,5在249 nm,332 nm和426nm有较强吸收;在375 nm激发波长激发下,5的最大发射波长在595 nm。     

Reaction of Methyl 1-(2-Bromoisobutyryl)cyclopentane-carboxylate and 3-(1-Bromocyclopentyl)-2,2-dimethyl-3-oxo-propionate with Zinc and Aromatic Aldehydes

Methyl 1-(2-bromoisobutyryl)cyclopentanecarboxylate and 3-(1-bromocyclopentyl)-2,2-dimethyl-3-oxopropionate react with zinc and aromatic aldehydes to afford 8-aryl-9,9-dimethyl-7-oxaspiro[4.5]decane-6,10-diones and 10-aryl-7,7-dimethyl-9-oxaspiro[4.5]decane-6,8-diones, respectively.     

Reaction of 2,2-dinitro-2-(3-phenyl-1,2,4-oxadiazol-5-l)acetonitrile with substituted phenyl azides

Russian Journal of Organic Chemistry -     

Reaction of 3-(dimethylamino)-2,2-dimethylpropanal with trialkylphosphites in the presence of acetic anhydride

Russian Journal of General Chemistry -     

Reaction of zinc enolates derived from 1-aryl-2,2-dibromoalkan-1-ones with tetramethyl 2,2′-(1,4-phenylenedimethylidene)dimalonate,dimethyl 3,3′-(1,4-phenylene)bis(2-cyanoacrylate), and 2,2′-(1,4-phenylenedimethylidene)-bis(malononitrile)

Zinc enolates derived from 1-aryl-2,2-dibromoalkanones reacted with tetramethyl 2,2′-(1,4-phenylenedimethylidene)dimalonate, dimethyl 3,3′-(1,4-phenylene)bis(2-cyanoacrylate), and 2,2′-(1,4-phenylenedimethylidene)bis(malononitrile) to give, respectively, tetramethyl 3,3′-(1,4-phenylene)bis(2-alkyl-2-aroylcyclopropane-1,1-dicarboxylates), dimethyl 3,3′-(1,4-phenylene)bis(2-alkyl-2-aroyl-1-cyanocyclopropane-1-carboxylates), and 3,3′-(1,4-phenylene)bis(2-alkyl-2-aroylcyclopropane-1,1-dicarbonitriles) as a single stereoisomer.     

Synthesis of N-(2-Benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-Benzene-2,2- dichloroethylidene)-4-methylbenzenesulfonamide

In reaction of N,N-dichloro-4-chlorobenzene- and N,N-dichloro-4-methylbenzenesulfonamides with phenylacetylene were obtained in good yield N-(2-benzene-2,2-dichloroethylidene)arenesulfonamides. The latter undergo nucleophilic addition of water, ethanol, and arenesulfonamides.     

Copolymerization of 2,2-diallyl-1,1,3,3-tetraethylguanidinium chloride with N-substituted maleimides

The free-radical copolymerization of 2,2-diallyl-1,1,3,3-tetraethylguanidinium chloride with N-phenyl- and N-p-carboxyphenylmaleimide is studied in bulk and in organic solvents. It is shown that copolymerization proceeds to form copolymers with a high tendency toward alternation of monomer units. The kinetic laws of the reaction are investigated, and the relative activities of the monomers are determined. It is found that 2,2-diallyl-1,1,3,3-tetraethylguanidinium chloride is involved in copolymerization with N-substituted maleimides to give rise to pyrrolidinium structures. This work was supported by the Russian Foundation for Basic Research (project no. 09-03-00220) and the by the Presidium of the Russian Academy of Sciences through the program Development of Methods of Synthesis of Chemical Substances and the Creation of Novel Materials.     

Copolymerization of 2,2-diallyl-1,1,3,3-tetraethylguanidinium chloride with vinyl acetate

The free-radical copolymerization of 2,2-diallyl-1,1,3,3-tetraethylguanidinium chloride with vinyl acetate in bulk and organic solvents has been studied. Copolymerization is shown to produce random copolymers. The kinetic features of the process are examined, and the relative activities of the monomers are estimated. 2,2-Diallyl-1,1,3,3-tetraethylguanidinium chloride is involved in copolymerization with vinyl acetate via both double bonds to give rise to pyrrolidinium structures.     

Nitration of 2-(2-quinolyl)thiophene and 5-(2-quinolyl)-2,2′-dithiophene

2-(2-Quinolyl)thiophene is nitrated in the 5 position, while its 2-thiophenyl analog is nitrated in the 3′ and 5′ positions simultaneously.