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1.
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
2.
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
3.
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
4.
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
5.
A. E. Shchekotikhin E. K. Shevtsova V. F. Traven’ 《Russian Journal of Organic Chemistry》2007,43(11):1686-1695
4,11-Dialkoxyanthra[2,3-b]furan-5,10-diones containing various substituents in the 3-position were synthesized. Reactions of these compounds with primary and secondary amines resulted in nucleophilic replacement of one or two alkoxy groups by the corresponding amine residues. 4,11-Dialkoxy derivatives of anthra[2,3-b]furan-5,10-dione showed fluorescence with large Stokes shifts (170–200 nm). 相似文献
6.
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
7.
A. E. Shchekotikhin E. P. Baberkina V. N. Buyanov K. F. Turchin N. N. Suvorov 《Chemistry of Heterocyclic Compounds》1998,34(7):813-815
Some electrophilic substitution reactions characteristic of indole derivatives have been investigated for 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione. The corresponding 3 derivatives were obtained as a result of Vilsmeier, Mannich, and acylation reactions.See [1] for Part 7.Russian Chemico-Technological University, Moscow 125190. Center for Drug Chemistry, All-Russian Chemical and Pharmaceutical Research Institute, Moscow 119815. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 939–941, July, 1998. 相似文献
8.
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
9.
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
10.
A. E. Shchekotikhin Yu. N. Lusikov V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2007,43(1):82-87
A new method for the synthesis of 2,3-diamino-1,4-dimethoxyanthraquinone from quinizarin has been developed. Heterocyclic
analogs of 5,12-naphthacenequinone have been synthesized based on this o-diamine-4,11-dimethoxyanthra[2,3-d]imidazole-5,10-dione,
4,11-dimethoxyanthra[2,3-d][1,2,3]triazole-5,10-dione, and 5,12-dimethoxynaphtho[2,3-g]quinoxaline-6,11-dione.
On the 70th Birthday of Professor E. Lukevics.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.1, 96–102, January 2007. 相似文献
11.
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
12.
Yu. E. Ivanov A. A. Yavolovsky A. V. Mazepa S. P. Krasnoshchekaya 《Chemistry of Heterocyclic Compounds》2003,39(2):250-254
5,10-Dioxo-5H,10H-diimidazo[1,5-a;1',5'-d]pyrazine-5,10-dicarboxylic acid dichloride in Friedel-Crafts reaction conditions formed with benzene the corresponding 1,6-dibenzoyl derivative 2, which reacted with alcohols and amines to give the keto esters and keto amides of 4(5)-benzoylimidazol-5(4)-carboxylic acids. The reaction of compound 2 with hydrazine gave substituted imidazo[4,5-f]pyridazine, and with o-phenylenediamine gave a derivative of imidazo[4,5-f]-1,4-benzodiazocine - a new heterocyclic system. 相似文献
13.
T. V. Shokol O. A. Lozinskii A. V. Turov V. P. Khilya 《Chemistry of Heterocyclic Compounds》2009,45(9):1089-1094
The reaction of 6-ethyl-8-formyl-7-hydroxy-3-(4-phenyl-4H-1,2,4-triazol-3-yl)chromone with 2-azolyl-acetonitriles gave 8-iminopyrano[2,3-f]chromen-4-ones, whose acid hydrolysis led to pyrano-[2,3-f]chromene-4,8-diones containing azaheterocyclic substituents at C-3 and C-9. 相似文献
14.
A. E. Shchekotikhin E. K. Shevtsova Yu. N. Luzikov V. A. Barachevskii V. F. Traven’ 《Russian Journal of Organic Chemistry》2008,44(6):855-862
Nucleophilic replacement of the hydroxy groups in ethyl 4,11-dihydroxy-2-methyl-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-carboxylate by chlorine upon treatment with phosphorus acid chlorides gave the corresponding 4(11)-chloro derivatives which were converted into photochromic ethyl 4(11)-phenoxy-2-methyl-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-carboxylates. Photoinduced decomposition of the latter leads to the formation of phenol and fluorescent hydroxyanthra[2,3-b]furandiones. 相似文献
15.
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
16.
Omar Khoumeri 《Tetrahedron letters》2009,50(46):6372-6180
We report herein an original and rapid synthesis of 2-substituted-4,11-dimethoxy-anthra[2,3-b]furan-5,10-diones by TDAE strategy followed by Palladium-catalyzed cyclo-etherification reaction. 相似文献
17.
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
18.
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
19.
The Pechmann reaction of 4-hydroxycoumarins with cyclohexanone and ethyl cyclopentanone-2-carboxylates affords 1,2,3,4-tetrahydro[2]benzopyrano[4,3-c][1]benzopyran-5,12-diones and cyclopenta[3′,4′]pyrano-[3,2-c][1]benzopyran-4,11-diones. Dehydrogenation of the former yields [2]benzopyrano[4,3-c][1]benzopyran-5,12-diones. Alkaline hydrolysis of a typical compound Va affords 2-hydroxy-2′-carboxydeoxybenzoin which on boiling with acetic anhydride gives an isocoumarin derivative. 相似文献
20.
The conversion of 2-acylamino-3-amino-1,4-naphthoquinones (II) to the corresponding 2-substituted 1H-naphth[2,3-d]imidazole-4,9-diones (I) under both alkaline and acid catalyzed conditions has been effected and the results compared. Treatment of 3-(4′-chlorobutanonyl-amino)-3-amino-1,4-naphthoquinone (He) with aqueous ethanolic sodium hydroxide solution gives 1,2-butanonaphth[2,3-d]imidazole-4,9-dione (V); whereas, treatment of lie with refluxing formic acid gave 2-(4′-chlorobutyl)-1H-naphth[2,3-d]imidazole-4,9-dione. Treatment of 2-substi-tuted 1H-naphth[2,3-d]imidazole-4,5-diones in DMF with alkyl halides in the presence of potassium carbonate affords the expected 1,2-disubstituted naphth[2,3-d]imidazole-4,9-diones (VI). The spectral properties of I, II, V and VI as well as those of some 2-acylamino-3-chloro-1,4-naphthoquinones IV are discussed. 相似文献