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1.
A. E. Shchekotikhin I. G. Makarov V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2005,41(7):914-920
The amination of 2-nitroquinizarine using hydroxylamine gives 2-amino-3-nitroquinizarine, which, upon reduction, gives previously
unreported 2,3-diaminoquinizarine, a key intermediate in the synthesis of heterocyclic analogs of 5,12-naphthacenequinone,
namely, 4,11-dihydroxyanthra[2,3-d]imidazole-5,10-dione (imidazoloquinizarine), 4,11-dihydroxyanthra[2,3-d][1,2,3]triazole-5,10-dione
(triazoloquinizarine), and 5,12-dihydroxynaphtho[2,3-g]quinoxaline-6,11-dione (pyrazinoquinizarine).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1081–1088, July, 2005. 相似文献
2.
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
3.
A. E. Shchekotikhin Yu. N. Luzikov V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2006,42(9):1236-1241
A preparative synthetic method has been developed for 3-chloro-2-formyl-1,4-dimethoxyanthraquinone starting from available
2-methylquinizarine. The condensation of the α-chloroaldehyde obtained with acetone oxime gives 4,11-dimethoxyanthra[2,3-d]isoxazole-5,10-dione.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1421–1427, September, 2006. 相似文献
4.
A. E. Shchekotikhin Yu. N. Luzikov V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2009,45(2):151-160
During the condensation of 2,3-dichloroquinizarine with methyl pivaloylacetate in the presence of potassium carbonate in dimethyl
sulfoxide the main reaction products are derivatives of angular 3-pivaloylanthra[1,2-b]furan-2,6,11(3H)-trione (about 70%) and anthra[2,1-d][1,3]dioxole-6,11-dione (15%), whereas the yield of the targeted linear methyl 2-tert-butyl-4,11-dihydroxyanthra[2,3-b]furan-5,10-dione-3-carboxylate is only 2%. Methods are developed for modification of the obtained 3-pivaloylanthra[1,2-b]furan-2,6,11(3H)-trione, making it possible to use it for the synthesis of the tert-butyl derivatives of linear anthra[2,3-b]furan-5,10-dione or angular anthra[1,2-b]furan-6,11-dione.
*For Communication 7 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 191–202, February, 2009. 相似文献
5.
A. E. Shchekotikhin Yu. N. Luzikov V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2006,42(6):746-752
Nucleophilic substitution of methoxy groups in 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione by the action of primary and
secondary alkylamines, or arylamines leads to the formation of N-alkyl or N-aryl derivatives of 4,11-diaminonaphtho[2,3-f]indole-5,10-dione
respectively. 4,11-Diamino-1H-naphtho-[2,3-f]indole-5,10-dione is obtained by the dealkylation of 4,11-bis[(1-phenylethyl)amino]-1Hnaphtho[
2,3-f]indole-5,10-dione in the presence of a Lewis acid (BBr3).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 854–861, June, 2006. 相似文献
6.
Yu. B. Sinkevich A. E. Shchekotikhin Yu. N. Luzikov V. N. Buyanov L. V. Kovalenko 《Chemistry of Heterocyclic Compounds》2007,43(10):1252-1259
4,11-Dihydroxyanthra[2,3-b]thiophene-5,10-dione (thiophenoquinizarine) and its 3-methyl derivative were obtained by the cyclization
of quinizarin-2-yl derivatives of mercaptoacetaldehyde or mercaptoacetone in acid medium. 4,11-Dimethoxy-and 4,11-dibutoxyanthra[2,3-b]thiophene-5,10-dione
were synthesized by the alkylation of the hydroxyl group in the synthesized anthrathiophenes with dimethylformamide dimethylacetal
or butyl iodide respectively. Radical bromination of 4,11-dimethoxy-3-methylanthra[2,3-b]thiophene-5,10-dione, depending on
the amount of N-bromo-succinimide taken, leads to the formation of 3-bromomethyl-or 3-dibromomethyl-4,11-dimethoxy-anthra[2,3-b]thiophene-5,10-diones.
The action of sodium acetate on the obtained bromo derivatives with subsequent hydrolysis of the intermediate acetates led
to the synthesis of 3-hydroxymethyl-or 3-formyl-4,11-dimethoxy-anthra[2,3-b]thiophene-5,10-diones.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1478–1485, October, 2007. 相似文献
7.
A. E. Shchekotikhin E. P. Baberkina K. F. Turchin V. N. Buyanov N. N. Suvorov 《Chemistry of Heterocyclic Compounds》2001,37(8):944-948
4,11-Dihydroxynaphtho[2,3-f]indole-5,10-dione (pyrroloquinizarin), its 11-dehydroxy derivative, and Mannich base were synthesized by demethylation of previously obtained methoxynaphtho[2,3-f]indole-5,10-diones. 相似文献
8.
A. E. Shchekotikhin E. P. Baberkina K. F. Turchin V. N. Buyanov N. N. Suvorov 《Chemistry of Heterocyclic Compounds》2000,36(11):1284-1288
N-Acetylation and several N-alkylation reactions have been carried out for the previously synthesized 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione. 相似文献
9.
A. E. Shchekotikhin Yu. N. Luzikov O. S. Anisimova V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2006,42(5):605-610
On methylating 4,11-dimethoxynaphtho[2,3-f]indazole-5,10-dione with methyl iodide in the presence of base a mixture is formed
of its 1-and 2-methyl derivatives. Demethylation of the methoxy groups of the starting material and of the products of its
alkylation leads to the formation of 4,11-dihydroxynaphtho[2,3-f]indazole-5,10-dione (pyrazoloquinizarine) and its 1-and 2-methyl
derivatives.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 691–696, May, 2006. 相似文献
10.
Alexander S. Tikhomirov Andrey E. Shchekotikhin Yuri N. Luzikov Alexander M. Korolev Maria N. Preobrazhenskaya 《Tetrahedron》2014
A new facile route to the synthesis of 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione and its novel 2-substituted derivatives was proposed. The developed scheme was based on a Pd-catalyzed cross-coupling/heterocyclization domino reaction of 3-bromo-2-hydroxy-4,11-dimethoxyanthraquinone with terminal alkynes. 相似文献
11.
A. E. Shchekotikhin Y. N. Luzikov Y. B. Sinkevich V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2008,44(10):1245-1249
On chlorination of 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione with sulfuryl chloride in chloroform, its mono-, di-, and trichloro derivatives are formed depending on
the conditions. Hydrolysis of the di- and trichloro derivatives gives a new polycondensed derivative of isatin, 4,11-dimethoxynaphtho-[2,3-f]isatin-5,10-dione. Its demethylation occurs effectively on extended heating with HBr in acetic acid and leads to 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-dione (4,11-di-hydroxynaphtho[2,3-f]indole-2,3,5,10-tetraone).
*For Communication 6 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1532–1536, October, 2008. 相似文献
12.
A. E. Shchekotikhin D. A. Silaev E. P. Baberkina I. G. Makarov V. N. Buyanov N. N. Suvorov 《Chemistry of Heterocyclic Compounds》2002,38(5):543-546
The previously unknown 4,11-dimethoxynaphtho[2,3-f]indazole-5,10-dione has been obtained by the thermal cyclization of N-nitroso derivative of 2-acetamido-3-methyl-1,4-dimethoxyanthraquinone. 相似文献
13.
A. S. Tikhomirov A. E. Shchekotikhin Yu. N. Luzikov A. M. Korolev M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2012,47(10):1206-1211
A new method was developed for synthesis of anthra[2,3-b]furan-5,10-dione derivatives. The key compound for annelation of the furan fragment to the anthraquinone chromophor is the
previously unknown analog of salicylaldehyde, 1,4-dimethoxy-3-formyl-2-hydroxyanthraquinone, which we have synthesized by
the Miller–Loudon–Schneider reaction. A chain of sequential transformations was used for its conversion into the target 4,11-dihydroxyanthra[2,3-b]furan-5,10-dione (furanoquinizarine): O-alkylation of the starting formylhydroxyanthraquinone with bromoacetic acid esters,
cyclo-dehydration of the 3-formylanthraquinon-2-ylacetic acid esters in the presence of bases, hydrolysis of the obtained
esters to 4,11-dimethoxy-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-2-carboxylic acid, its decarboxylation, and demethylation of the obtained 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione. 相似文献
14.
N. I. Mukarramov B. A. Urakov Kh. M. Shakhidoyatov 《Chemistry of Heterocyclic Compounds》2007,43(9):1210-1213
A study was carried out on the oxidative cyclocondensation of 2-thioxothieno-and 2-thioxopyrido[2,3-d]pyrimidin-4-ones. The
thiophene ring with excess π-electron density facilitates the reaction, while the pyridine ring with diminished π-electron
density hinders it. 2-Thioxothieno-[2,3-d]pyridimin-4-ones were converted into previously unreported 7H,13H-[1,2,4]thiadiazolo-[3,2-b:5,4-b′]bis(thieno[2,3-d]pyridimine-7,13-diones).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1424–1427, September, 2007. 相似文献
15.
A. V. Zadorozhny V. A. Kovtunenko A. V. Turov T. T. Kucherenko 《Chemistry of Heterocyclic Compounds》2008,44(7):845-851
Treatment of 2-(4-oxo-3,4-dihydrothieno[2,3-d]-and-[3,2-d]pyrimidin-2-ylmethyl)benzoic acids and 2-(4-oxo-3,4-dihydro-2-quinazolinylmethyl)benzoic
acid with acetic anhydride gave thieno[3′,2′:5,6]-and-[2′,3′:5,6]pyrimido[1,2-b]isoquinoline-4,11-diones and isoquino[2,3-a]quinazoline-5,12-dione
respectively. NMR spectroscopy showed that an intramolecular acylation of the above acids occurs at the atom N-1 of the pyrimidinone
part of the bicycle.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1053–1061, July, 2008. 相似文献
16.
It has been shown that 1-aryl-8-(4-bromophenyl)-4,6-dioxo-2H(phenyl)-7-phenyl-1,4,6,7,8,9-hexahydropyrimido[4,5-b][1,6]naphthyridines are formed on heating anilides of 1-aryl-7-(4-bromostyryl)-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acids in PPA.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, 597–600, April, 2005. 相似文献
17.
A. N. Nikitina A. E. Shchekotikhin Y. N. Luzikov A. M. Korolev V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2011,47(2):194-203
A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding
derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-diones. Successive halogenation using phosphorus penta-chloride and acylation of tert-butylamine by the intermediate
2-chloro derivative converted 4,11-di-methoxynaphtho[2,3-f]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative. 相似文献
18.
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
19.
Omar KhoumeriGamal Giuglio-Tonolo Maxime D. CrozetThierry Terme Patrice Vanelle 《Tetrahedron》2011,67(34):6173-6180
We report herein an original and rapid synthesis of 2-substituted-4,11-dimethoxy-1-(phenylsulfonyl)-2,3-dihydro-1H-naphtho[2,3-f]indole-5,10-diones by TDAE mediated synthesis of N-benzylsulfonamides followed by an intramolecular N-arylation using Cu-catalyzed system. 相似文献
20.
Heating of 6-amino-1,3-dimethyluracil with hexafluoroacetone and ethyl trifluoropyruvate benzoylimines in DMF in the presence of Et3N results in 1,3-dimethyl-7-phenyl-5,5-bis(trifluoromethyl)-1,2,3,4,5,8-hexahydropyrimido[4,5-d]pyrimidine-2,4-dione and 5-benzoylamido-1,3-dimethyl-5-trifluoromethyl-1,2,3,4,5,6-hexahydropyrrolo[2,3-d]pyrimidine-2,4,6-trione, respectively. 相似文献