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1.
S. A. Yamashkin N. V. Zhukova I. S. Romanova 《Chemistry of Heterocyclic Compounds》2008,44(7):793-801
It was established that the initial condensation of substituted 6-aminoindoles and oxaloacetic ester in boiling benzene with
the addition of catalytic amounts of acetic acid takes place exclusively through the carboxyl group of the keto ester with
the formation of the corresponding enamines, which successfully undergo thermal cyclization (biphenyl, 280°C) to pyrroloquinolines.
Here, irrespective of the nature of substituents at the N-1 and C-5 atoms enamines with a free position 7 are transformed
into pyrrolo-[2,3-f]quinolines (structural analogs of vitamin PQQ) while 7-OMe-substituted enamines give pyrrolo[3,2-g]quinolines
with linear fusion of the rings.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 991–1002, July, 2008. 相似文献
2.
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
3.
N. N. Polygalova A. G. Mikhailovskii E. V. Vikhareva M. I. Vakhrin 《Chemistry of Heterocyclic Compounds》2007,43(7):900-905
It has been shown that the Chichibabin reaction of enamines of the 1,2,3,4-tetrahydroisoquinoline series and 1,2,3,4-tetrahydrobenzo[f]isoquinoline
series with p-bromophenacyl bromide leads to pyrrolo[2,1-a]isoquinoline derivatives. The same heterocyclic system is obtained
on interaction of 1-alkyl-3,4-dihydroisoquinolines or their benzo[f]-analogs with oxalyl chloride. The obtained dioxopyrrolines
form derivatives of benzo[g]quinoxalino[2,3-b]indolizine on condensation with o-phenylenediamine.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1068–1074, July, 2007. 相似文献
4.
T. I. Mukhanova L. M. Alekseeva A. S. Shashkov V. G. Granik 《Chemistry of Heterocyclic Compounds》2004,40(1):16-21
Derivatives of furo[2,3-f]quinoline were synthesized by the reaction of the enamines of acetylacetone and benzoylacetone with 2-methoxycarbonyl-4-oxo-5,8-quinolinequinone. A derivative of pyrrolo[2,3-h]quinoline was obtained from N-benzyl--aminocrotonic ester. 相似文献
5.
S. A. Yamaskhin G. A. Romanova E. A. Oreshkina N. V. Zhukova 《Chemistry of Heterocyclic Compounds》2006,42(1):77-85
It has been shown that the condensation reaction of 5-amino-2,3-dimethyl-and 1,2,3-trimethylindoles with 4,4,4-trifluoroacetoacetic
ester occurs either via the trifluoromethylcarbonyl or the ester group depending upon the conditions under which it is carried
out. Under thermal conditions (refluxing in diphenyl) the enaminocrotonates formed are readily converted to pyrrolo[3,2-f]quinolines
and the amides cyclize in trifluoroacetic acid at 78°C to give pyrrolo[2,3-g]quinolines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 86–96, January, 2006. 相似文献
6.
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
7.
S. V. Tolkunov A. I. Khyzhan S. Yu. Suikov V. I. Dulenko 《Chemistry of Heterocyclic Compounds》2005,41(3):379-386
Condensation of hetarene carboxaldehydes with phthalide gave 2-(3-hydroxy-1-oxoinden-2-yl)benzo[b]furan and 2-(3-hydroxy-1-oxoinden-2-yl)-5-ethylthieno[2,3-b]thiophene. Starting from hetaryl acetic acids gave 3-(3-hydroxy-1-oxoinden-2-yl)benzo[b]furan and 3-(3-hydroxy-1-oxoinden-2-yl)benzo[b]thiophene. Acylation of 3-hydroxy-1-oxoinden-2-yl-substituted heterocycles using acetic anhydride in the presence of 70% HClO4 leads to the formation of pentacyclic pyrilium salts. Pentacyclic indenopyridines are prepared by treating the pyrilium salts with ammonia. The reaction of the carbonyl group in the indenopyridines with hydroxylamine, hydrazine hydrate, and in reduction using NaBH4 has been studied.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 435–443, March, 2005. 相似文献
8.
S. M. Medvedeva E. V. Leshcheva Kh. S. Shikhaliev A. S. Solov’ev 《Chemistry of Heterocyclic Compounds》2006,42(4):534-539
Based on the reaction of 8-R-4,5-dihydro-4,4-dimethyl[1,2]dithiolo[3,4-c]quinoline-1-thiones with oxalyl chloride followed
by the reactions of 1,3-dipolar cycloaddition and diene synthesis with participation of acetylenedicarboxylic acid dimethyl
ester, we have developed approaches to synthesis of novel polycondensed heterocyclic systems: [1,2]dithiolo[3,4-c]pyrrolo[3,2,1-ij]quinoline-4,5-dione,
6-(1,3-dithiol-2-ylidene)-1,2-dioxo-5-thioxo-7H-pyrrolo[3,2,1-ij]quinoline and 4,5-dioxospiro(pyrrolo)-[3,2,1-ij]thiopyrano[2,3-c]quinoline-11,2′-[1,3]dithiole.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 610–615, April, 2006. 相似文献
9.
N. N. Polygalova A. G. Mikhailovskii M. I. Vakhrin 《Chemistry of Heterocyclic Compounds》2006,42(10):1352-1357
The reaction of p-benzoquinone with enamino amides derived from 2,2-dimethyl-1,2,3,4-tetrahydrobenzo[f]isoquinoline proceeds
through a Michael addition. The reaction of this quinone with the base of drotaverine leads to a derivative of indolo[2,1-a]isoquinoline.
Fusion of isoquinoline enamines by the action of 2,3-dichloro-1,4-naphthoquinone leads to pentacyclic benzo[g]naphtho-[2,3-b]indolyzine-8,13-dione.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1565–1570, October, 2006. 相似文献
10.
E. Suloeva M. Yure E. Gudriniece S. Belyakov M. Petrova I. Kalnite 《Chemistry of Heterocyclic Compounds》2001,37(3):329-337
Syntheses are reported for a series of 2-alkylamino-6-phenyl-4-trifluoromethylpyridines. The reaction of 3-cyano-2-(hydroxyalkylamino)-6-phenyl-4-trifluoromethylpyridines with thionyl chloride gave the corresponding 2-(chloroalkylamino)pyridines, 8-cyano-5-phenyl-7-trifluoromethyl-2,3-dihydro-imidazo[1,2-a]pyridines, and 9-cyano-6-phenyl-8-trifluoromethyl-2,3,4-trihydropyrido[1,2-a]-pyrimidines. X-ray diffraction structural analysis was used to study 8-cyano-5-phenyl-7-trifluoromethyl-2,3-dihydroimidazo[1,2-a]pyridine. 相似文献
11.
L. M. Potikha V. M. Kisil A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2008,44(7):838-844
Treatment of 5-aryl-3-halo-12H-isoquino[2,3-a]quinazolines with electrophilic reagents readily forms their oxidation products.
Acylation of the 3-chloro-5-phenyl-7,12-dihydroisoquino[2,3-a]quinazolinium perchlorate with Ac2O in the presence of pyridine gave the product of electrophilic substitution at the C-7 atom 1-(3-chloro-5-phenyl-12H-isoquino[2,3-a]quinazolin-7-yl)-1-ethanone.
By the same route phenacyl bromides react with the anhydro base 1 to give 5-aryl-7-(2-aryl-2-oxoethyl)-3-halo-isoquino[2,3-a]quinazolin-13-ium bromides. These salts readily react with nucleophilic
reagents to form the products of addition at the C-12 atom.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1044–1052, July, 2008. 相似文献
12.
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
13.
Atef A. Hamed Ibrahim F. Zeid Hussein H. El-Ganzory Mohamed T. Abdel Aal 《Monatshefte für Chemie / Chemical Monthly》2008,139(7):809-820
A series of substituted thieno[2,3-d]pyrimidines was synthesized starting from ethyl-2-amino-4-isopropylthiophene-3-carboxlate. Reaction of 2-hydrazino-5-isopropyl-thieno[2,3-d]pyrimidin-4(3H)-one and its 3-methyl analogue with different reagents afforded thieno[2,3-d]triazolo[4,3-a]pyrimidines and thieno[3,2-e]triazolo[4,3-a]pyrimidines, beside open chain derivatives.
Correspondence: Atef A. Hamed, Department of Chemistry, Faculty of Science, Menoufia University, Shebin El Koam, Egypt. 相似文献
14.
S. A. Yamashkin E. A. Oreshkina I. S. Romanova M. A. Yurovskaya 《Chemistry of Heterocyclic Compounds》2006,42(1):86-91
The reaction of 6-amino-2,3-dimethyl-and 6-amino-1,2,3-trimethyl-5-methoxy(methyl)indoles with 4,4,4-trifluoroacetoacetic
ester and of 6-amino-5-methoxy-1,2,3-trimethylindole also with other β-dicarbonyl compounds has been studied. It was found
that all of the amines investigated undergo condensation readily to form the corresponding enamines while the possible subsequent
cyclization to give pyrrolo[2,3-f]quinolines was found only for the condensation product of 6-amino-2,3,5-trimethylindole
with 4,4,4-trifluoroacetoacetic ester.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp 97–103, January, 2006. 相似文献
15.
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
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.
The compact synthesis of a new ring fused benzo[b]thieno derivative with an embedded nine-membered ring system via ring closing metathesis methodology is described. The preparation of the novel 11H-benzo[b]thieno[2,3-c]pyrrolo[2,3-a]indol-11-one via palladium-mediated oxidative cyclisation of benzo[b]thien-2-oyl indole derivatives is also reported. 相似文献
18.
V. S. Tolkunov Yu. B. Vysotsky O. A. Gorban’ S. V. Shishkina O. V. Shishkin V. I. Dulenko 《Chemistry of Heterocyclic Compounds》2005,41(4):515-525
We have studied the reactions of 3-arylaminobenzofuro-, 3-arylaminobenzothieno-, and 3-arylaminoindolo[2,3-c]pyrylium salts with ammonium acetate, primary amines, and hydrazine hydrate. In an alcoholic medium, primary amines and hydrazine hydrate open up the pyrylium ring to form arylamides of 2-(N-benzylmethylketimine)hetaryl-3-acetic acids or the corresponding hydrazones, where further heterocyclization does not occur. Upon treatment with ammonium acetate in acetic acid, 2-aryl-1-methylhetero[2,3-c]pyridin-3-(2H)-ones are formed along with their 2-unsubstituted analogs.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 601–612, April, 2005. 相似文献
19.
S. A. Yamashkin G. A. Romanova I. S. Romanova M. A. Yurovskaya 《Chemistry of Heterocyclic Compounds》2003,39(9):1188-1196
The behavior of 5-amino-2-phenyl- and 5-amino-1-methyl-2-phenylindoles in reactions with acetoacetic, trifluoroacetoacetic, and ethoxymethylenemalonic esters, leading to the preparation of pyrrolo[2,3-g]- and pyrrolo[3,2-f]quinolines with functional substituents has been studied. 相似文献
20.
Katarzyna Ostrowska Katarzyna SzymoniakMagdalena Szczurek Krzysztof Jamro?y Maria R?pa?a-Kozik 《Tetrahedron》2011,67(29):5219-5227
The regioselective syntheses of substituted pyrrolo[2,3-b]quinoxaline, pyrido[2,3-b]pyrrolo[2,3-e]pyrazine, pyrido[2,3-b]pyrrolo[3,2-e]pyrazine and pyrido[3,4-b]pyrrolo[3,2-e]pyrazine are reported. Differential reactivity between two amino groups in ortho-diaminopyridine can be exploited to obtain new regio-defined unsymmetrical pyridopyrrolopyrazine derivatives. Weak electron-donating methyl or moderately electron-withdrawing carboxylic groups attached to the aromatic ortho-diamines reduce the regioselectivity of obtaining unsymmetrical substituted pyrrolo[2,3-b]quinoxaline. The fluorescence properties of the resultant 1-alkyl pyridopyrrolopyrazine and substituted pyrrolo[2,3-b]quinoxaline derivatives are presented. 相似文献