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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.
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
3.
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
4.
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
5.
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.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.1, 96–102, January 2007. 相似文献
6.
Mohammad Bagher Teimouri Reihaneh Bazhrang 《Monatshefte für Chemie / Chemical Monthly》2008,139(8):957-961
An efficient and clean green synthesis of highly substituted linear naphtho[2,3-b]-furan-4,9-dione derivatives, starting from 2-hydroxy-1,4-naphthoquinone, alkyl isocyanides and a variety of aldehydes, is
described. This new method provides the first example of an efficient regioselective synthetic method for the synthesis of
linear naphtho[2,3-b]-furan-4,9-dione ring systems by formation of three bonds. This [3 + 1 + 1] furannulation strategy affords furanonaphthoquinones
in moderate to high yields, using water as a cheap, non-toxic, environmentally friendly solvent, in a one-step reaction, without
the need of complicated work-up procedures.
Correspondence: Mohammad Bagher Teimouri, Petrochemical Department, Iran Polymer and Petrochemical Institute, P.O. Box 14965-115,
Tehran, Iran. 相似文献
7.
M. A. Mzhelskaya I. D. Ivanchikova N. E. Polyakov A. A. Moroz M. S. Shvartsberg 《Russian Chemical Bulletin》2004,53(12):2798-2804
Procedures were developed for the heterocyclization of 2-benzoylethynyl-1-hydroxy-and 1-hydroxy-2-(1-oxo-3-phenylpropynyl)anthraquinone. The regioselective preparation of 2-substituted anthra[1,2-b]pyran-4,7,12-triones was demonstrated to be possible under mild conditions.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2686–2692, December, 2004. 相似文献
8.
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).
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1081–1088, July, 2005. 相似文献
9.
The acylation of benzo[b]furan-, benzo[b]thiophene, and indolyl-3-acetic acid arylamides using acetic anhydride in the presence of 70% perchloric acid occurs at the -position of the heterocycle to give 2-acetylbenzo[b]furan-, 2-acetylbenzo[b]thiophene, and 2-acetylindolyl-3-acetic acid arylamides. Depending on the amount of perchloric used in the reaction they undergo cyclodehydration to 3-arylamino-1-methylhetero[2,3-c]pyrilium salts and to N-aryl-1-methyl-3(2H)hetero[2,3-c]pyridones. 相似文献
10.
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
11.
We have established that when 5-chloro-6-[cyano(2,3-dihydro-1-R-benzo[d]azol-2-yl)methyl]-2,3-pyrazinedicarbonitriles are reacted with nucleophilic reagents (aliphatic and aromatic amines, hydrogen sulfide), annelation of the five-membered ring occurs on the [b] face of the pyrazine with formation of 6-amino-7-hetaryl-5-R-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles and 6-amino-7-(1H-benzo[d]imidazol-2-yl)thieno[2,3-b]pyrazine-2,3-dicarbonitrile respectively. Further heating with excess of acylating reagent leads to formation of a novel heterocyclic system 1H-benzo[4,5]imidazo[1,2-c]pyrazino[2',3':4,5]pyrrolo[3,2-e]pyrimidine. Reaction of vicinal dinitriles with hydrazine hydrate leads to the novel system 1H-pyrrolo[2',3':5,6]pyrazino[2,3-d]pyridazine. 相似文献
12.
The reactions of 2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione with dimethyl sulfate, benzyl chloride, and allyl bromide afforded the corresponding 2-alkyl-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-triones and 3-(alkoxy)-6,11-dihydroanthra[2,1-d]isothiazole-6,11-diones. The reactions of 2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione and its S-oxide with a formaldehyde—secondary amine system yielded 2-[(alkylamino)methyl]-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-triones and 2-[(alkylamino)methyl]-3,6,11-trioxo-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole 1-oxides, respectively. 相似文献
13.
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.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1478–1485, October, 2007. 相似文献
14.
Boguslavskiy A. M. Ponizovskiy M. G. Kodess M. I. Charushin V. N. 《Russian Chemical Bulletin》2003,52(10):2175-2184
Pyrazolo[3,4-b]-, isoxazolo[4,5-b]-, benzo[2,3]-1,4-diazepino-, and benzo[2,3]-1,4-oxazepinoquinoxalines were prepared by reactions of 2-quinoxalinecarboxaldehyde with 1,2-N,N-, 1,2-N,O and 1,4-N,N- and 1,4-N,O-dinucleophiles. 相似文献
15.
The interaction of 4-allyl-5-phenyl-1,2,4-triazole-3-thione with iodine proceeds with the formation of a mixture of 6-iodomethyl-3-phenyl-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole and 6-iodo-3-phenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b]-1,3-thiazine. The structures of the cyclization products obtained were established on the basis of the 1H NMR spectra of their dehydroiodinated derivatives. 6-Methyl-3-phenylthiazolo[2,3-c]-1,2,4-triazole, 3-phenyl-5H-1,2,4-triazolo[3,4-b]-1,3-thiazine, and 3-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3-thiazine are formed on eliminating HI from the cyclization products. 相似文献
16.
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
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.
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
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 538–543, April, 2007. 相似文献
19.
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
20.
A. V. Kurkin K. V. Bukhryakov M. A. Yurovskaya 《Chemistry of Heterocyclic Compounds》2009,45(2):188-193
The sequence of steps including nucleophilic substitution of the chlorine atom in 2-chloro-3-nitropyridine by esters of optically
active phenylalanine, reduction of the nitro group, acylation with ethyl oxalyl chloride, and intramolecular cyclization,
leads to the synthesis of derivatives of 1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-2,3-dione with a chiral substituent at the nitrogen atom. It was established that, depending on the conditions of
carrying out the cyclization, the parallel formation of derivatives of imidazo[4,5-b]pyridine is possible. Conditions were found for selectively carrying out the cyclization under with only structures of pyrazines
or imidazole condensed with pyridine were formed.
Dedicated to Academician J. Stradins in connection with his 75th jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 237-243, February, 2009. 相似文献