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1.
E. A. Kaigorodova L. D. Konyushkin M. E. Niyazymbetov S. N. Kvak V. N. Zaplishny V. P. Litvinov 《Russian Chemical Bulletin》1994,43(12):2095-2099
A series of substituted 2-alkyl(aryl-, hetaryl-)thiopyridines was prepared by cathodic electrolysis of thiols in the presence of 2-chloro-3-cyano-4-methoxymethyl-6-methylpyridine or 4-chloro-6-methyl-3-oxo-1H-furo[3,4-c]pyridine. The reaction of 3-cyano-4-methoxymethyl-6-methyl-2(1H)-thiopyridone with alkyl halides in the presence of KOH is regioselective and leads toS-alkyl derivatives. The advantages of electrosynthesis for the preparation of 2-alkylthiopyridines fused with 2(5H)-furanone and of 3-aminothieno [2,3-b]pyridines is demonstrated.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2215–2219, December, 1994. 相似文献
2.
3-Amino-2-(isoxazol-3-yl)-4-methoxymethyl-6-methylthieno[2,3-b]pyridine was synthesized by the reaction of 2(1H)-thioxopyridine-3-carbonitrile with 3-chloromethylisoxazole in the presence of two equivalents of KOH. Boiling of 3-amino-2-(isoxazol-3-yl)-4-methoxymethyl-6-meth-ylthieno[2,3-b]pyridine with Raney nickel results in 4-aminothieno[2,3-b;4,5-b′]dipyridine or 5-(4-amino-2-pyridyl)pyridine depending on the reaction conditions.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 669–670, March, 2008. 相似文献
3.
E. A. Kaigorodova L. D. Konyushkin S. N. Mikhailichenko V. K. Vasilin A. V. Sazonov V. G. Kul'nevich 《Chemistry of Heterocyclic Compounds》1999,35(3):293-296
Nucleophilic substitution of the chlorine atom in 2-chloro-3-cyano-6-methoxymethyl-4-methylpyridine by mercapto group produces the corresponding 2(1H)-pyridinethione, alkylation of which by halogenated compounds in the presence of KOH proceeds regioselectively to form S-alkyl derivatives. Thorpe—Ziegler cyclization of S-alkyl derivatives, which contain an active methylene group, yields new 3-aminothieno[2,3-b]-pyridines.Kuban State Technological University, Krasnodar 350072, Russia, and N. D. Zelinskii Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow 117913; e-mail: stud@issep.rssi.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 337–341, March, 1999. 相似文献
4.
E. A. Kaigorodova V. K. Vasilin M. M. Lipunov V. E. Zavodnik G. D. Krapivin 《Chemistry of Heterocyclic Compounds》2004,40(12):1600-1608
Iminophosphoranes containing a thieno[2,3-b]pyridine fragment were obtained through a sequence of reactions: 1) alkylation of 3-cyano-2(1H)-pyridinethiones in alkaline medium by an -halocarbonyl compound with subsequent Thorpe-Ziegler cyclization of the resultant 2-thioalkylpyridines to give 3-aminothieno[2,3-b]pyridines, 2) diazotization of the amino group and nucleophilic substitution of the diazonium group by an azido group without isolation of the diazonium salts, and 3) reaction of the 3-azidothieno[2,3-b]pyridines with triphenylphosphine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1853–1862, December, 2004. 相似文献
5.
4-Aryl-3-cyano-6-phenylpyridine-2(1H)-thiones, used in the synthesis of substituted 2-alkylthiopyridines, thieno[2,3-b]pyridines,
and 1,4-di(pyridin-2-ylthio)butane, have been synthesized by the condensation of arylmethylenecyanothioacetamides with benzoyl-1,1,1-trifluoroacetone.
The reaction path includes the formation of the Michael adduct which undergoes loss of the acyl group. The structure of 3-cyano-2-methylthio-4-(1-naphthyl)-6-phenylpyridine
has been studied by X-ray crystallography.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, 1821–1828, December 2005. 相似文献
6.
Condensation of propanal with cyanothioacetamide and morpholine gave 3-cyano-4-ethyl-5-methyl-6-morpholino-2-piperidone, the
structure of which was studied by X-ray analysis. Reaction of propanal with cyanothioacetamides and cycloalkanone enamines
gave 3-cyano-4-ethyl-2,5,6,7-tetrahydropyrindin-2(1H)-one and 3-cyano-4-ethyl-5,6-hexamethylenepyridine-2(1H)-thione. The
latter was used for the preparation of substituted 2-benzyloxycarbonylmethylthiopyridine and 3-amino-2-benzyloxycarbonylthieno[2,3-b]pyridine.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1053–1059, July, 2005. 相似文献
7.
H. Kažoka A. Krauze M. Vilums L. Černova L. Sīle G. Duburs 《Chemistry of Heterocyclic Compounds》2007,43(6):708-714
The stability of solutions of esters of 6′-carbamoylmethylthio-5′-cyano-2′-methyl-1′,4′-dihydro-4,4′-bipyridine-3′-carboxylic
acids was investigated by HPLC. The corresponding esters of 6′-carbamoylmethylthio-5′-cyano-4,4′-bipyridine-3′-carboxylic
acids,esters of 8-cyano-5-methyl-3-oxo-7-(4-pyridyl)-2,3-dihydro-7H-thiazolo-[3,2-a]pyridine-6-carboxylic acids, methyl 3-amino-2-carbamoyl-6-methyl-4-(4-pyridyl)-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate,
and methyl 3-amino-2-carbamoyl-6-methyl-4-(4-pyridyl)-thieno[2,3-b]pyridine-5-carboxylate were synthesized as standard compounds
(typical impurities). Analysis by HPLC was realized under the conditions of reverse-phase chromatography. It was established
that solutions of the investigated compounds (with mixtures of acetonitrile with phosphate buffer, having pH values of not
less than 3 and not more than 5, as solvents) are stable for one month when the solutions are stored in a place protected
against light. It is also necessary to use chromatographic systems in which the aqueous components have pH 3–5 during determination
of the purity of the esters of 6′-carbamoylmethylthio-5′-cyano-2′-methyl-1′,4′-dihydro-4, 4′-bipyridine-3′-carboxylic acid
by HPLC in order to separate the analyzed sorbates and their typical impurities more completely.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 841–848, June, 2007. 相似文献
8.
We have obtained 4-alkyl-6-amino-5-cyano-3-methyl(propyl, phenyl)-2H,4H-pyrano[2,3-c]pyrazoles by reaction of 4-alkylmethylene-3-substituted 5-pyrazolones with malononitrile or cyanothioacetamide. We have used X-ray diffraction to study the structure of 6-amino-5-cyano-4-isopropyl(hexyl)-3-phenyl-2H,4H-pyrano[2,3-c]pyrazoles. 相似文献
9.
E. S. Kostenko M. M. Lipunov E. A. Kaigorodova L. D. Konyushkin 《Chemistry of Heterocyclic Compounds》2007,43(11):1466-1476
The reaction of acyl derivatives of ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate with hydrazine hydrate gives a series
of tricyclic 3-amino-3,4-dihydropyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4-ones containing aliphatic, aromatic, or heteroaromatic
fragments at C(2). The reactions of 3-aminopyridothieno[3,2-d]pyrimidin-4-ones with aldehydes, formamide, 2,5-dimethoxytetrahydrofuran, acetic
anhydride, and Raney nickel were studied.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1720–1732, November, 2007. 相似文献
10.
V. V. Dotsenko S. G. Krivokolysko B. P. Litvinov 《Chemistry of Heterocyclic Compounds》2007,43(5):599-607
The reaction of diketene with cyanothioacetamide in dry dioxane in the presence of triethylamine gives triethylammonium 3-cyano-6-methyl-4-oxo-1,4-dihydro-2-pyridinethiolate.
The regioselective S-alkylation of this thiolate is a convenient method for the preparation of substituted 4(1H)-pyridones
and also derivatives of thiazolo[3,2-a]pyridine and thieno[2,3-b]pyridine. The action of 2-amino-1,1,3-tricyanopropene on
this thiolate leads to its transformation into a new heterocyclic system, namely, 5H-pyrido[2′,3′:4,5]thiopyrano[2,3-b]pyridine;
treatment with iodine yields the oxidation product, namely, the corresponding bis(2-pyridyl) disulfide. The structure of isopropyl
(3-cyano-6-methyl-4-oxo-1,4-dihydro-2-pyridinyl)thioacetate was confirmed by X-ray diffraction structural analysis.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 716–725, May, 2007. 相似文献
11.
E. I. Kaigorodova L. D. Konyushkin S. N. Mikhailichenko V. K. Vasilin V. G. Kul'nevich 《Chemistry of Heterocyclic Compounds》1996,32(10):1234-1238
The alkylation of 6-methyl-4-methoxymethyl-3-cyano-2-(1H)pyridinethione by halogen derivatives in the presence of KOH proceeds regioselectively with the formation of S-alkyl derivatives. By cathodic electrolysis of the thiols in the presence of 6-methyl-4-methoxymethyl-2-chloro-3-cyanopyridine, 2-arylthiopyridines are obtained. By Thorpe-Ziegler cyclization of 2-alkylthiopyridines having an ctive methylene group, 2-aminothieno[2,3-b]pyridines have been synthesized.Kuban State Technological University, Krasnodar, 350072. N. D. Zelinskii Institute of Organic Chemistry, Moscow 117913. Southern Branch of Association Rosvuznauka, Krasnodar, 350072. Translated from Khimiya Geterotsiklicheskikh Soedinenii, NO. 10, pp. 1432–1437, October, 1996. Original article submitted April 2, 1996; revision submitted August 20, 1996. 相似文献
12.
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
13.
A. E. Shchekotikhin Yu. N. Lusikov V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2007,43(4):439-444
Condensation of 2-formyl-or 2-cyano-3-chloro-1,4-dimethoxyanthraquinone with methyl thioglycolate in the presence of base
gave methyl 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylate and its 3-amino derivative respectively. Hydrolysis
of the ester group in methyl 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylate and subsequent decarboxylation
of the carboxylic acid formed gave 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione. Condensation of 3-chloro-2-formyl-1,4-dimethoxyanthraquinone
with ammonia in the presence of sulfur gave 4,11-dimethoxyanthra[2,3-d]isothiazole-5,10-dione
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 538–543, April, 2007. 相似文献
14.
The reactions of 1-substituted 2-nitro-3-phenylaminoprop-2-en-1-ones with cyanothioacetamide afforded the corresponding 6-substituted 3-cyano-5-nitropyridine-2(1H)-thiones, which were used for the synthesis of 6-substituted 3-cyano-2-methylthio-5-nitropyridines and 7-substituted 4-hydroxy-8-nitropyrido[2",3":4,5]thieno[2,3-b]pyridin-2(1H)-ones. 相似文献
15.
K. G. Nikishin V. N. Nesterov V. P. Kislyi A. M. Shestopalov V. V. Semenov 《Russian Chemical Bulletin》1998,47(4):679-681
4-Methoxy-1,1,1-trifluoropent-3-en-2-one reacts with cyanothioacetamide to give 3-cyano-4-methyl-6-trifluoromethylpyridine-2(1H)-thione, which was transformed into 3-amino-4-methyl-6-trifluoromethylthieno[2,3-b]pyridine-2-carboxanilide by the reaction with chloroacetanilide. The crystal and molecular structure of the amide obtained
was studied by X-ray analysis.
Translated fromIzvestiya Akademii Nauk Seriya Khimicheskaya, No. 4, pp. 701–703, April, 1998. 相似文献
16.
Yu. M. Volovenko T. A. Volovnenko F. S. Babichev T. Shevchenko 《Chemistry of Heterocyclic Compounds》1994,30(4):453-457
The acylation of 3-amino-4-cyano-1(2H)isoquinolines with benzoyl chloride leading to the formation of 1,3 oxazino[4,5-clisoquinoline-6-ones has been studied. Previously undescribed 1-aminopyrimido[4,5-cJisoquinolirt 6-ones have been obtained by the reaction of the appopriate 3-amino-](2H)isoginolones with formamide. Nucleophilic replacement has been carried out with 3-amino-1-chloroisoquinoline by the action of sodium hydroxide, primary alcohols, hydrazine hydrate, and various amines. 1,2,4-Triazino[2,3-b]isoginolone has been synthesized by condensing 2,3-diamino-1 (2H)isoquinolone with mesoxalic acid ethyl ester. 相似文献
17.
7-Acetyl-8-aryl-2-(1-chloro-2-hydroxy-3-propyl)thio-9-cyano-6-methyl-1,4-dihydropyridines were obtained by treatment of 1,4-dihydropyridine-2(3H)-thiones
with epichlorohydrin in the presence of sodium bicarbonate. When treated with NaOMe, these compounds are readily intramolecularly
alkylated with formation of 7-acetyl-8-aryl-3-hydroxy-9-cyano-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b]-[1,3]thiazines. We
have studied amination of 2-(1-chloro-2-hydroxy-3-propyl)thio-1,4-dihydropyridines and acylation of 3-hydroxy-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1394–1399, September, 2005. 相似文献
18.
The Claisen condensation of ethyl 2-ethoxy-6-methylpyridine-3-carboxylate with ethyl acetate gave ethyl 2-ethoxy-6-methylnicotinoylacetate, which was converted to 3-bromo-acetyl-6-niethyl-2-pyridone by heating with bromine in 48% hydrobromic acid. The cyclization of the bromoacetylpyridone by the action of silver oxide in methanol gave 3-oxo-6-methyl-2,3-dihydrofuro[2,3-b]pyridine, which was reduced to 3-hydroxy-6-methyl-2,3-dihydrofuro[2,3-b]pyridine with lithium aluminum hydride in dimethoxyethane. Acetylation of the latter gave its acetate, the pyrolysis of which in vacuo gave 6-methylfuro[2,3-b]-pyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1544–1546, November, 1972. 相似文献
19.
K. G. Nikishin V. P. Kislyi V. N. Nesterov A. M. Shestopalov Yu. T. Struchkov V. V. Semenov 《Russian Chemical Bulletin》1998,47(3):465-468
The reaction of trifluoroacetylacetone with cyanothioacetamide proceeded regioselectively to form 3-cyano-6-methyl-4-trifluoromethylpyridine-2(1H)-thione from which the corresponding 2-alkylthiopyridines and 3-aminothieno[2,3-b]pyridines were obtained. The crystal and molecular structure of 3-cyano-2-ethylthio-6-methyl-4-trifluoromethylpyridine was established by X-ray diffraction analysis. 相似文献
20.
Yuh-Wen Ho 《中国化学会会志》1999,46(6):955-962
Coupling the diazonium salt of 3-amino-2-cyano-4,6-dimethylthieno[2,3-b]pyridine 1 with malononitrile 2 gave 2-cyano-3-(hydrazonomalononitrile)-4,6-dimethylthieno[2,3-b]pyridine 3 which then reacted with hydrazine compounds 4a-4h to yield corresponding 2-cyano-3-(3,5-diamino-1-substituted-pyrazol-4-yl)azo-4,6-dimethylthieno[2,3-b]pyridines 5a-5h. The 2-cyano-3-(2-amino-5,7-disubstituted-pyrazolo-[1,5-a]pyrimidine-3-yl)azo-4,6-dimethylthieno[2,3-b]pyridines 7a-7f were obtained in good yield by the cyclocondensation reaction of 2-cyano-3-(3,5-diamino-pyrazol-4-yl)azo-4,6-dimethylthieno[2,3-b]pyridine 5a with the appropriate 1,3-diketones 6a-6f under acidic condition. 相似文献