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1.
Ya. S. Kayukov S. V. Karpov O. V. Kayukova O. V. Ershov O. E. Nasakin 《Russian Journal of Organic Chemistry》2014,50(8):1097-1106
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. 相似文献
2.
S. V. Karpov Ya. S. Kayukov I. N. Bardasov O. V. Ershov O. E. Nasakin O. V. Kayukova 《Russian Journal of Organic Chemistry》2011,47(8):1161-1164
Reactions of 2-aroyl-1,1,3,3-tetracyanopropenides with thiols in acid medium led to the formation of the corresponding 2-alkylsulfanyl-substituted
2-(5-amino-2-aryl-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles. 相似文献
3.
Ya. S. Kayukov A. A. Grigor’ev S. V. Karpov Yu. A. Gracheva O. V. Kayukova 《Russian Journal of Organic Chemistry》2017,53(12):1884-1886
Enolizable 1-(tetracyanocyclopropyl)alkanones reacted with aqueous alkali metal hydroxides to give, depending on the alkali concentration, 2-(5-amino-2-alkylidene-4-cyano-2,3-dihydrofuran-3-ylidene)-propanedinitriles or 2-(4-alkyl-3-amino-2-cyano-5-oxo-cyclopent-2-en-1-ylidene)propanedinitriles. 相似文献
4.
Ievlev M. Yu. Mayorov N. S. Shishlikova M. A. Belikov M. Yu. Bardasov I. N. Ershov O. V. 《Russian Journal of Organic Chemistry》2021,57(12):1961-1967
Russian Journal of Organic Chemistry - Previously unknown 2-{4-aryl-5-cyano-[2,2′-bipyridin]-6(1H)-ylidene}malononitriles were synthesized by reaction of... 相似文献
5.
A. A. Grigor’ev S. V. Karpov O. E. Nasakin V. A. Tafeenko O. V. Kayukova Ya. S. Kayukov 《Russian Journal of Organic Chemistry》2018,54(3):503-505
The reaction of potassium 2-(2,2-dimethylpropanoyl)-1,1,3,3-tetracyanopropenide with an equimolar amount of 2-sulfanylethanol afforded 2-{5-amino-2-(tert-butyl)-4-cyano-2-[(2-hydroxyethyl)sulfanyl]- 2,3-dihydrofuran-3-ylidene}propanedinitrile, whereas 4-amino-1-(tert-butyl)-1,6-bis[(2-hydroxyethyl)- sulfanyl]-3-imino-1,3-dihydrofuro[3,4-c]pyridine-7-carbonitrile was obtained in the reaction with excess 2-sulfanylethanol. 相似文献
6.
D. V. Ivanov N. M. Igidov S. N. Shurov M. V. Dmitriev I. N. Chernov 《Russian Journal of Organic Chemistry》2018,54(4):573-577
Ethyl 2-amino-5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carboxylates and 2-amino- 5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carbonitriles reacted with alcohols in the presence of a catalytic amount of concentrated aqueous HCl to give the corresponding 5-alkoxy-2-amino-5-(2-aryl-2- oxoethyl)-4-oxo-1H-4,5-dihydrofuran-3-carboxylic acid derivatives. A probable reaction mechanism was proposed on the basis B3LYP/6-311G(d) quantum chemical calculations. 相似文献
7.
I. N. Bardasov O. V. Kayukova Ya. S. Kayukov O. V. Ershov M. Yu. Belikov O. E. Nasakin 《Chemistry of Heterocyclic Compounds》2009,45(9):1035-1038
A new preparative method was developed for the synthesis of 2-(2-alkoxy-5-amino-4-cyano-2-methyl-3(2H)-ylidene)malononitriles
in a single stage from readily obtainable reagents. 相似文献
8.
E. S. Vostrov E. V. Leont'eva O. P. Tarasova A. N. Maslivets 《Russian Journal of Organic Chemistry》2004,40(7):1058-1061
Thermal decarbonylation of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones gives rise to intermediate aroyl(phenyl)ketenes which react with nonactivated Schiff bases, N,N'-dicyclohexylcarbodiimide, and p-di-methylaminobenzonitrile according to the [4 + 2]-cycloaddition pattern with formation of 6-aryl-5-phenyl-4H-1,3-oxazin-4-ones. Reactions of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones with activated Schiff bases at a temperature below the thermolysis temperature lead to 4-aroyl-4-phenyltetrahydropyrrole-2,3-diones. 相似文献
9.
E. N. Koz’minykh V. I. Goncharov V. O. Koz’minykh 《Russian Journal of Organic Chemistry》2007,43(6):864-867
2-[2-(4-Chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one and methyl (5-aryl-3-oxo-2,3-dihydrofuran-2-ylidene)acetates react with carboxylic acid hydrazides to give the corresponding 3-substituted 2-acyl-6-aryl-3-hydroxy-2,3-dihydropyridazin-4(1H)-ones. Specificities of the product structure are discussed. 相似文献
10.
S. V. Fedoseev M. Yu. Belikov O. V. Ershov I. N. Bardasov V. A. Tafeenko 《Russian Journal of Organic Chemistry》2016,52(10):1440-1443
2-Aminoprop-1-ene-1,1,3-tricarbonitrile (malononitrile dimer) reacted with 1-arylpropane-1,2-diones in ethanol in the presence of piperidine to give new donor–acceptor chromophores, 2-[4-aryl-3-cyano-5-hydroxy-5-methyl-1H-pyrrole-2(5H)-ylidene]malononitriles. 相似文献
11.
E. N. Koz''minykh N. N. Trapeznikova E. A. Chupilova N. M. Igidov V. O. Koz''minykh 《Russian Journal of Organic Chemistry》2001,37(1):116-118
Treatment of acetophenone and dibenzoylmethane with excess oxalyl chloride gave heterocyclization products, 2-(3-oxo-5-phenyl-2,3-dihydrofuran-2-ylidene)-5-phenyl-2,3-dihydrofuran-3-one and a mixture of 4-benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dione with 4-benzoyl-2-dibenzoylmethylene-5-phenyl-2,3-dihydrofuran-3-one. 相似文献
12.
L. M. Potikha A. A. Lysakovskii V. A. Kovtunenko A. V. Turov 《Russian Journal of Organic Chemistry》2009,45(12):1818-1823
5-(4-Chlorophenyl)- and 5-phenylfuran-2(3H)-ones reacted with guanidine carbonate at the methylene group in the unsaturated lactone molecule, leading to the formation
of 4-(2-aryl-5-oxo-2,5-dihydrofuran-2-yl)-5-aryltetrahydrofuran-2-ones, while 5-(4-methylphenyl)furan-2(3H)-one under analogous conditions gave rise to N,N′-bis[4-(4-methylphenyl)-4-oxobutanoyl]guanidine. The reactions of 5-arylfuran-2(3H)- ones with thioacetamide afforded 4-aryl-N-{1-[5-aryl-2-oxo-2,3-dihydrofuran-3-ylidene]ethyl}-4-oxobutanamides. The corresponding N-(4-aryl-4-oxobutanoyl)thioureas were obtained by heating 5-arylfuran-2(3H)-ones with thiourea. 相似文献
13.
Rodinovskaya L. A. Gromova A. V. Shestopalov A. M. Nesterov V. N. 《Russian Chemical Bulletin》2003,52(10):2207-2213
Substituted 3-hydroxypyrazoles, which were prepared based on ethyl esters of substituted 4-(pyridin-2-ylthio)- or 4-(1,4-dihydropyridin-2-ylthio)acetoacetic acids and hydrazine hydrate, were used in the synthesis of 6-amino-4-aryl-5-cyano-3-(pyridin-2-ylthiomethyl)-2,4-dihydropyrano[2,3-c]pyrazoles. The molecular and crystal structure of 6-amino-5-cyano-3-(3-cyano-4,6-dimethylpyridin-2-ylthiomethyl)-4-(2-nitrophenyl)-2,4-dihydropyrano[2,3-c]pyrazole was established by X-ray diffraction analysis. 相似文献
14.
A. I. Ozols Yu. Ê. Pelcher Z. A. Kalme Yu. Yu. Popelis I. V. Turovskis G. Ya. Duburs 《Chemistry of Heterocyclic Compounds》1996,32(1):52-58
8-Aryl-7-acetyl-1, 6-dimethyl-6-hydroxy-4-cyano-5, 6, 7, 8-tetrahydro-3(2H)-isoquinolinones and -isoquinolinethiones and their sodium salts were obtained by the reaction of cyanoacetamide and cyanothioacetamide with 3-aryl-2, 4-diacetyl-5-methyl-5-hydroxycyclohexanonesinbasicrnedium. 8-Aryl-7-acetyl-6-methoxycarbonyl-1, 6-dimethyl-4-cyano-5, 6, 7, 8-tetrahydro-3(2H)-isoquinolinones were obtained by the reaction of acetyl chloride and the above isoquinolinone sodium salts. The reaction of iodoacetamide and the above isoquinolinethione sodium salts yielded 8-aryl-7-acetyl-3-carbamoylmethylthio-1, 6-dimethyl-4-cyano-5, 6, 7, 8-tetra-hydroisoquinolines, which were cyclized into 1-amino-6-aryl-7-acetyl-2-carbamoyl-5, 8-dimethyl-8-hydroxy-6, 7, 8, 9-tetrahydrothiophene[2,3-c]isoquinolines in basic medium. 相似文献
15.
Recyclization of 5-arylfuran-2,3-diones under the action of ethyl cyanoacetate or of malonic acid dinitrile resulting in the corresponding esters or nitriles of 2-amino-5-(2-aryl-2-oxoethylidene)-4-oxo-1Н-4,5-dihydrofuran-3-carboxylic acids was investigated. 相似文献
16.
4-Cyano-2,3-dihydrofuran-3-carboxamides were obtained from the oxidative cyclization of 3-oxopropanenitriles with unsaturated amides using manganese(III) acetate. Treatment of 3-oxopropanenitriles with (2E)-3-(5-methyl-2-furyl)acrylamide and (2E)-3-(2-thienyl)acrylamide gave 2-(5-methyl-2-furyl) and 2-(2-thienyl) substituted 4-cyano-2,3-dihydrofuran-3-carboxamides in moderate yields, respectively. However, (2E)-3-(2-furyl)acrylamide and (2E)-3-phenylacrylamide did not produce any product under the same conditions. On the other hand, reaction of a dienamide such as (2E,4E)-5-phenylpenta-2,4-dienamide with 3-oxopropanenitriles gave diastereomeric mixtures of 2-(2-vinylphenyl)-4-cyano-2,3-dihydrofuran-3-carboxamides. Mechanisms are proposed for the formation of all of these compounds. 相似文献
17.
Vostrov E. S. Leont'eva E. V. Tarasova O. P. Maslivets A. N. 《Russian Journal of Organic Chemistry》2003,39(1):103-107
Aroyl(phenyl)ketenes generated by thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones undergo [4+2]-cyclodimerization to 3-aroyl-6-aryl-3,5-diphenyl-3,4-dihydro-2H-pyran-2,4-diones. Heating of the latter leads to rearrangement with formation of 4-aroyloxy-6-aryl-3,5-diphenyl-2H-pyran-2-ones. Thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones in the presence of carbonyl compounds yields 6-aryl-5-phenyl-4H-1,3-dioxin-4-ones. 相似文献
18.
Yu. S. Andreichikov D. D. Nekrasov M. A. Rudenko A. Yu. Konovalov 《Chemistry of Heterocyclic Compounds》1987,23(6):610-613
On reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with -aminoisobutyronitrile, o-aminobenzonitrile, and -anilinopropiononitrile, we obtained aroylpyruvic acid N-(1-methyl-1-cyanoethyl)-, N-(o-cyanophenyl)-, and N-phenyl-N-(cyanoethyl)-amides, respectively. On reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with cyanoacetamide we obtained aroylacetic acid N-(cyanoacetyl)amides, while in the case of methyleneaminoacetonitrile and p-dimethylaminobenzonitrile we obtained (6-aryl-4-oxo-2,3-dihydro-1,3-oxazin-3-yl)acetonitriles and 2-(p-dimethylaminophenyl)-6-aryl-1,3-oxazine-4-ones, respectively.For Communication 2, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 740–743, June, 1987. 相似文献
19.
Costa M Areias F Abrunhosa L Venâncio A Proença F 《The Journal of organic chemistry》2008,73(5):1954-1962
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-2H-chromene-3-carbonitriles 1, (2-amino-3-cyano-4H-chromen-4-yl)malononitriles 2, 4-amino-5-imino-2,7-dimethoxy-5H-chromeno[3,4-c]pyridine-1-carbonitrile 12, and (4,5-diamino-1-cyano-1,10b-dihydro-2H-chromeno[3,4-c]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 Aspergillus 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 Aspergillus alliaceus was reduced by about 93% with a 200 microM 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. 相似文献
20.
V. O. Koz'minykh E. N. Koz'minykh Yu. S. Andreichikov 《Chemistry of Heterocyclic Compounds》1989,25(8):862-865
Reaction of 5-aryl-4-halo-2,3-dihydrofuran-2,3-diones with alkoxycarbonylmethylenetriphenylphosphoranes has given 2-alkoxycarbonylmethylene-5-aryl-4-halo-2, 3-dihydrofuran-3-ones, which readily add halogens at the 2-exocyclic double bond, and on reaction with arylamines recyclize to give 2-hydroxy-2, 3-dihydropyrrol-3-ones.For Communication 1, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1034–1038, August, 1989. 相似文献