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1.
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
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E. G. Paronikian Sh. F. Akopian A. S. Noravian 《Chemistry of Heterocyclic Compounds》2008,44(8):1003-1008
A new methods have been developed for the synthesis of condensed pyrido[2,3-b]thieno[3,2-d]pyrimidines based on cyclic derivatives
of 4-cyanopyridine-3-thiones. The presence of two different reactive functional groups NH2 and CONH gives the possibility of carrying out different conversions of thieno[2,3-b]pyridines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, 1245–1252, August, 2008. 相似文献
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Ya. Yu. Yakunin V. D. Dyachenko V. P. Litvinov 《Chemistry of Heterocyclic Compounds》2001,37(6):766-770
The reaction of ethoxymethylenacetylacetanilide with cyanothioacetamide or cyanoselenoacetamide in the presence of N-methylmorpholine and alkylating agents gave substituted 2-alkylthio- and 2-alkylselenopyridines and thieno[2,3-b]pyridines. 相似文献
6.
A new convenient method is proposed for the preparation of 3-aryl- and 2-styrylimidazo[1,5-a]pyridines involving the cyclocondensation of 2-(acylaminobenzyl)pyridines in acetic anhydride with adding of p-toluenesulfonic acid.Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 252660 Kiev; e-mail: olga@elan-ua.net. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 640–642, May, 2000. 相似文献
7.
S. I. Moryashova L. K. Salamandra A. E. Fedorov L. A. Rodinovskaya A. M. Shestopalov V. V. Semenov 《Russian Chemical Bulletin》1998,47(2):357-360
Reactions of sodium derivatives of 2- and 3-thenoylacetaldehydes with cyanothioacetamide gave 2- and 3-cyano-6-thienylpyridine-2(1H)-thiones, which were used in the synthesis of substituted 2-alkylthiopyridines, thieno[2,3-b]pyridines, and other fused heterocycles.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 365–368, February, 1998. 相似文献
8.
We have developed a method for obtaining 2-substituted 3-amino-6,6-dimethyl-5,6-dihydro-8H-pyrano[4′,3′:4,5]-and 5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4(3H)-ones,
converted by deamination to the corresponding dihydropyranothieno-3H-pyrimidinones.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 441–444, March, 2006. 相似文献
9.
H. Kažoka A. Krauze M. Viļums L. Černova L. Sīle G. Duburs 《Chemistry of Heterocyclic Compounds》2007,43(1):50-57
Esters of 6′-carbamoylmethylthio-5′-cyano-1′,4′-dihydro-3,4′-bipyridine-3′-carboxylic acids are obtained by the alkylation
of piperidinium 3′-alkoxycarbonyl-5′-cyano-1′,4′-dihydro-3,4′-bipyridine-6′-thiolates with iodoacetamide. For an HPLC study
of the stability of solutions of the abovementioned 1,4-dihydrobipyridines (solution pH 2.3–9.0) the appropriate esters of
6′-carbamoylmethylthio-5′-cyano-3,4′-bipyridine-3′-carboxylic acids and esters of 8-cyano-5-methyl(or phenyl)-3-oxo-7-pyridin-3-yl-2,3-dihydro-7H-thiazolo[3,2-a]pyridine-6-carboxylic
acids were synthesized as reference compounds. Analysis by HPLC was carried out under conditions of reverse-phase chromatography.
It was shown that solutions of the investigated compounds in a mixture of acetonitrile and phosphate buffer (pH 3.0–5.0) were
stable for 1 month on storage protected from light. Under the action of light in all the solutions investigated irrespective
of pH the formation occurs of the corresponding esters of 6′-carbamoylmethylthio-5′-cyano-3,4′-bipyridine-3′-carboxylic acids.
The presence of esters of 8-cyano-5-methyl(or phenyl)-3-oxo-7-pyridin-3-yl-2,3-dihydro-7H-thiazolo[3,2-a]pyridine-6-carboxylic
acids (no more than 4%) was detected only in 0.1% solutions of phosphoric acid (pH 2.3) under conditions of storage of the
latter protected from light. A series of as yet unidentified products was detected in solutions of pH 7.0–9.0.
Dedicated to E. Lukevics on his 70th birthday
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 59–68, January, 2007. 相似文献
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11.
S. M. Sherif 《Monatshefte für Chemie / Chemical Monthly》1996,127(5):557-568
Summary The reaction of phenyl isothiocyanate with arylsulfonylacetophenones1a–d in alkaline medium afforded the non-isolable intermediates2a–d. Upon reaction with some bromo compounds, the latter underwentin situ heterocyclization to afford the corresponding polyfunctionally substituted 2-(aroyl-(arylsulfonyl)-methylene)-2,3-dihydrothiazoles and-thiazolidin-4-ones. The structures of the newly synthesized compounds were assigned and confirmed on the basis of their elemental analyses, spectroscopic data, and alternative syntheses whenever possible.
Eine einfache Synthese von polyfunktionell substituierten 2-(Aroyl-(arylsulfonyl)-methylen)-2,3-dihydrothiazolen und -thiazolidin-4-onen und ihrer kondensierten Derivate
Zusammenfassung Die Reaktion von Phenylisothiocyanat mit den Arylsulfonylacetophenonen1a–d in alkalischem Medium führt zu den nicht isolierbaren Zwischenprodukten2a–d. Diese cyclisieren mit einigen Bromverbindungenin situ zu den entsprechenden polyfunktionell substituierten 2-(Aroyl-(arylsulfonyl)-methylen)-2,3-dihydrothiazolen und -thiazolidin-4-onen. Die Strukturen der neuen Verbindungen wurden aufgrund ihrer Elementaranalysen und ihrer spektroskopischen Daten aufgeklärt und, wenn möglich, durch alternative Synthesen bestätigt.相似文献
12.
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
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E. S. Komarova V. A. Makarov L. M. Alekseeva G. V. Avramenko V. G. Granik 《Russian Chemical Bulletin》2006,55(4):735-740
1-[4-Aminoarylpyrazolo[3,4-b]pyridin-5-yl]pyridinium chlorides undergo cyclization under reflux in tert-butanol in the presence of an excess of potassium tert-butoxide to form tetracyclic derivatives of pyrazolo[3,4-b]pyrido[1′,2′:1,2]imidazo[4,5-d]pyridine. The reaction scheme of the processes is proposed. The structures of the reaction products were confirmed by physicochemical
methods.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 710–714, April, 2006. 相似文献
15.
V. K. Vasilin . A. Kaigorodova S. I. Firgang G. D. Krapivin 《Chemistry of Heterocyclic Compounds》2004,40(3):377-386
We synthesized derivatives of a novel heterocyclic system, isoxazolo[3',4':4,5]thieno[2,3-b]pyridine by sequential conversions in three steps: isomerization of 2-(2-R-ethylthio-2-oxo)-3-pyridyl cyanides obtained by alkylation from substituted 3-cyano-2(1H)-pyridinethiones by -halomethyl ketones in alkaline medium, to form 3-aminothieno[2,3-b]pyridines; diazotization of the amino group followed by nucleophilic substitution of the diazonium group by an azido group, bypassing the step of isolating the diazonium salts; and thermolysis of the azides formed. 相似文献
16.
Synthetic approaches towards new condensed thienopyridine ring systems including furo[2,3-b]thieno[3,2-e]pyridines, bisthieno[2,3-b:3′,2′-e]pyridines, 5H-chromeno[2,3-b]thieno[3,2-e]pyridines, 5H-benzo(f)chromeno[2,3-b]thieno[3,2-e]pyridines have been achieved by application of intramolecular 4+2 cycloaddition reactions of suitably designed thieno[2,3-e][1,2,4]triazines tethered with alkene or alkyne terminals. 相似文献
17.
E. A. Kaigorodova A. A. Osipova L. D. Konyushkin G. D. Krapivin 《Russian Chemical Bulletin》2004,53(4):853-859
Reactions of 2,5-dimethoxytetrahydrofuran with 3-aminothieno[2,3-b]pyridines afford a number of substituted 3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridines. The possibility of the reaction and the yield of the product are determined by the character of a substituent in position 2 of thieno[2,3-b]pyridine. The Curtius rearrangement of 2-acylazido-3(1H-pyrrol-1-yl)thieno[2,3-b]pyridines yields 4,5-dihydropyrido[3",2":4,5]thieno[2,3-e]pyrrolo[1,2-a]pyrazin-4-ones. The molecular and crystal structures of ethyl 4-methoxymethyl-6-methyl-3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridine-2-carboxylate were determined by X-ray diffraction analysis. 相似文献
18.
Ján Halgaš Viera Kolenová Zuzana Števíková Lucia Perašínová Jozef Kožíšek 《Chemical Papers》2009,63(3):323-328
Although thienopyridines attract attention because of their biological activities, they have not been used as ligands in coordination
compounds. Thieno[2,3-b]pyridine was prepared by known procedures; by reduction of 2-nitrothiophene, and reaction of the resulting 2-thienyl ammonium
salt with malondialdehyde tetramethylacetal in the presence of zinc chloride. The same procedure was used for the preparation
of a new derivative, 2-methylthieno[2,3-b]pyridine, starting from 2-methyl-5-nitrothiophene. The thienopyridines were used in the synthesis of coordination compounds.
Chlorides, isothiocyanates, acetates, and chloroacetates of copper(II), nickel(II), or cobalt(II) were used as starting salts.
The prepared complexes were characterized by elemental analysis and FT IR. Structures of the four complexes were determined
by single-crystal X-ray diffraction analysis.
Presented at the 1st International Conference “Applied Natural Sciences” on the occasion of the 10th anniversary of the University
of Ss. Cyril and Methodius, Trnava, 7–9 November 2007. 相似文献
19.
L. Bukowski Z. Zwolska E. Augustynowicz-Kopec 《Chemistry of Heterocyclic Compounds》2006,42(10):1358-1365
The reactions of 2-acetylimidazo[4,5-b]pyridine hydrazone with some alkyl-and arylisothiocyanates and some orthoesters were
carried out. Various new derivatives of the titled compound such as thiosemicarbazones, ethoxymethylenehydrazones, and derivatives
of the new pyrido-[3′,2′:4,5]imidazo[1,2-d][1,2,4]triazine ring system were obtained. Biological data for selected compounds
are presented.
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1571–1579, October, 2006. 相似文献
20.
We have developed a method of synthesis of benzo[5,6]indolizino[2,1-b]quinolinium-13-thiolates and 5,6-dihydrobenzo[5,6]indolizino[1,2-c]quinoline-6-thiones
based on the reaction of the corresponding 1′, 2′-dialkyl-1′,2′-dihydro-2,3′-biquinolines and 1′,4′-dialkyl-1′,4′-dihydro-2,3′-biquinolines
with sulfur in DMF.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 849–851, June, 2007. 相似文献