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1.
Ivana Bradiaková Naďa Prónayová Anton Gatial Alžbeta Krutošíková 《Chemical Papers》2008,62(4):428-434
(E)-3-{5-[3-(Trifluoromethyl)phenyl]furan-2-yl}propenoic acid (I) was prepared from 5-[3-(tri-fluoromethyl)phenyl]furan-2-carbaldehyde under the Doebner’s conditions. The obtained acid was
converted to the corresponding azide II, which was cyclized by heating in diphenyl ether to 2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (III). This compound was aromatized with phosphorus oxychloride to chloroderivative IV which was reduced with H2NNH2-Pd/C to the title compound V. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridin-5-oxide (VI) was synthesized by reaction of V with 3-chloroperoxybenzoic acid in dichloromethane. On treatment of VI with benzoyl chloride and potassium cyanide (Reissert-Henze reaction), corresponding 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine-1-carbonitrile (VII) resulted. 5-Amino-2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridin-5-ium-4-methylbenzene sulfonate (VIII) was prepared by direct N-amination of the title compound V with 1-[(aminooxy)sulfonyl]-4-methylbenzene in dichloromethane. Then, VIII was transformed to a non-isolated zwitterionic N-imid IX which afforded the corresponding furo[3,2-c]pyrazolo[1,5-a]pyridine carboxylic acid esters X, XI by 1,3-dipolar cycloaddition reactions with dimethyl but-2-ynedionate (DBD) or ethyl propiolate. The structures of all compounds
were confirmed by their IR and NMR spectra.
Presented at the 1st International Conference “Applied Natural Sciences” on the occasion of 10th anniversary of the University
of St. Cyril and Methodius, Trnava, 7–9 November 2007. 相似文献
2.
Ivana Bradiaková Tatiana Ďurčeková Naďa Prónayová Anton Gatial Alžbeta Krutošíková 《Chemical Papers》2009,63(5):586-591
2-[3-(Trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (I) was prepared by a three-step synthesis. Its reaction with phosphorus sulfide rendered thione II which was methylated to 2-[3-(Trifluoromethyl)phenyl]-4-methylsulfanylfuro[3,2-c]pyridine (III). 5-Methyl-2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (IV) was obtained by the reaction of I with methyl iodide in PTC conditions. The chlorine atom in derivate V was replaced with heterocyclic secondary amines via nucleophilic substitution and 4-substituted furopyridines VIa and VIb were thus prepared. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridine-4-carboxylic acid (VII) was obtained by hydrolysis of the corresponding carbonitrile Va. 相似文献
3.
Peter Gajdoš Soňa Pavlíková Filip Bureš Alžbeta Krutošíková 《Central European Journal of Chemistry》2005,3(2):311-325
The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions
was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording
comparable yields. 相似文献
4.
The corresponding 1-(2-quinoxalyl)-, 1-[3,5-di(trifluoromethyl)phenyl]-, and 1-ethoxycarbonyl-3-methyl-4-oxo-4,5,6,7-tetrahydroindazoles have been obtained from reactions of 2-acetyl-1,3-cyclohexanedione, its 5,5-dimethyl and 5-(2-furyl) derivatives, with 2-hydrazinoquinoxaline, 3,5-di(trifluoromethyl)phenylhydrazine, and ethoxycarbonylhydrazine. On interaction with ethoxycarbonylhydrazine the intermediate 2-[1-(-ethoxycarbonyl)hydrazino]ethylidene-1,3-cyclohexanediones were also isolated. From the potassium salt of 2-formyldimedone and 2-carboxyphenylhydrazine hydrochloride, 2-(2-carboxyphenyl)hydrazinomethylene-5,5-dimethyl-1,3-cyclohexanedione was obtained, the cyclization of which in ethanol in the presence of HCl led to 1-(2-carboxyphenyl)- and 1-(2-ethoxycarbonylphenyl)-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindazole. 相似文献
5.
V. M. Kisil L. M. Potikha A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2008,44(2):214-224
The reaction of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones with o-xylidene dibromide leads to 11-oxo-4bH,5H,10H,11H,16H-10a-aza-15b-azoniadibenzo[a,e]pleiadene
bromides, which are converted to 11-oxo-10H,11H,16H-10a-aza-15b-azoniadibenzo[a,e]pleiadene salts upon oxidation using nitrobenzene.
The reaction of these salts with benzylamine leads to 6-{2-[(benzylimino)methyl]phenyl}-7,12-dihydroisoquino[3,2-b][2]benzazepin-14(6H)-ones,
which recyclize to 11-oxo-5H,10H,11H-10a-aza-15b-azoniadibenzo[a,e]pleiadene perchlorates upon the action of perchloric acid.
The reactions of the 10a,15b-diazadibenzo[a,e]pleiadene salts obtained with NaBH4 were studied and the structures of the reduction products were determined by spectral methods.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 280–292, February, 2008. 相似文献
6.
L. M. Potikha V. A. Kovtunenko A. V. Tarasevich 《Chemistry of Heterocyclic Compounds》2007,43(12):1551-1558
Oxidation of the hydrobromide of 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one with dimethyl sulfoxide leads to 11-hydroxy-11H-isoquino[3,2-b]quinazoline-6,13-dione,
and with hydrogen peroxide to the hydrobromide of 2-[(4-oxo-3,4-dihydro-2-quinazolinyl)carbonyl]benzoic acid. Salts of 5-and
6-alkyl-substituted isoquino[3,2-b]quinazolines are readily oxidized on boiling in nitrobenzene, which leads to aromatization
of the isoquino[3,2-b]quinazoline system to 5-methyl-13-oxo-5H,13H-isoquino[ 3,2-b]quinazolinium perchlorate and 6-benzyl-13H-isoquino[3,2-b]quinazolin-13-one.
The structures of the dehydrogenation products were established from 1H NMR and UV spectra. The interaction of the obtained compounds with NaBH4 has been studied.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1833–1840, December, 2007. 相似文献
7.
L. M. Potikha R. M. Gutsul A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2008,44(2):208-213
Condensation of 2-(cyanomethyl)benzoic acid with 2-aminobenzylamine gave 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-11-one.
Its oxidation in nitrobenzene led to the formation of 5,13,5′,13′-hexahydro[6,6′]bi[isoquino[3,2-b]quinazoline]-11,11′-dione,
but in dichlorobenzene in the presence of elemental sulfur and iodine it gave the rearrangement product 6H-dibenzo[b,f][1,8]naphthyridin-5-one.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.2, 273–279, February, 2008. 相似文献
8.
S. M. Ramsh A. G. Ivanenko V. A. Shpilevyi N. L. Medvedskiy P. M. Kushakova 《Chemistry of Heterocyclic Compounds》2005,41(7):921-928
Alkaline hydrolysis of 3-tert-butyl-7,7-bis(hydroxymethyl)-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]-triazin-6(7H)-one can occur in three directions: with cleavage of the tetrahydrotriazine ring, with cleavage of the
thiazolidine ring, and also with opening of both rings. Depending on the process conditions, either the hydrolysis product
corresponding to the first direction or the hydrolytic decomposition products corresponding to the second and third directions
can be obtained in preparative quantities. Hydrolysis of 3,3′-di-tert-butyl-3′,4′-dihydro-2′ H-spiro[(perhydro-1,3-oxazine)-5,7′-thiazolo[3,2-a][1,3,5]triazin]-6′-one in (NH4)2CO3 solution occurs in two steps: in the first step, cleavage of the tetrahydrotriazine ring occurs; and in the second step,
opening of the perhydrooxazine ring occurs.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1089–1097, July, 2005. 相似文献
9.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2006,42(3):396-402
We have studied the reaction of 2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-one and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones
with amines, alkylating reagents, and hydrogen peroxide. We have shown that the presence of an aryl substituent at the 2 position
of [1,3-thiazino[3,2-a]benzimidazol-4-ones has a substantial effect on the direction of the reactions.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 445–452, March, 2006. 相似文献
10.
M. A. Kukaniev S. Sh. Shukurov Yu. Khodzhibaev N. Kurbonova S. G. Bandaev 《Russian Chemical Bulletin》1998,47(11):2300-2301
2-Ethoxycarbonylmethyl-7-methyl-1,3,4-thiadiazolo[3,2-a]pyrimidin-5(5H)-one containing the active methylene group reacts easily with carbon disulfide and phenyl isothiocyanate in the presence
of sodium hydride. Further alkylation of the reaction product by alkyl halides results in the formation of the corresponding
1,3,4-thiadiazolo[3,2-a]pyrimidine derivatives containing a ketene dithioacetal fragment.
Deceased.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2371–2373, November, 1998. 相似文献
11.
M. M. Krayushkin M. A. Kalik D. V. Kozhinov A. Yu. Martynkin Yu. P. Strokach V. A. Barachevsky 《Chemistry of Heterocyclic Compounds》2005,41(3):312-316
1,2-Bis{5-(2-benzothiazolyl)-2-ethylthieno[2,3-b]thiophen-3-yl}hexafluorocyclopentene has been synthesized for the first time. It was shown that, unlike analogous derivatives of thieno[3,2-b]thiophene, on irradiation with UV light (λ = 313 nm) it did not display photochromic properties, but undergoes an irreversible photoconversion which is accompanied by the display of intense fluorescence. This raises the prospect of using this compound for creating an irreversible photoluminescent recording medium.Dedicated to V. I. Minkin on his 70th birthday.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 360–364, March, 2005.For Part 20 see [1]. 相似文献
12.
Interaction of 6,11-dihydro-13H-isoquino[2,3-b]quinazolin-13-one with alkylating agents occurs at two positions depending
on their nature and the reaction conditions-at C(6) or N(5). Fusion with methyl tosylate leads to 5-methyl-13-oxo-6,13-dihydro-11H-isoquino[3,2-b]quinazolin-5-ium salts, while interaction
with benzyl halides in the presence of i-PrONa gave 6-benzyl-and 6,6-dibenzyl-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones.
Alkylation with olefins led to two types of products. In the case of maleinimides and maleic acid anhydride Michael adducts
at C(6) were formed and in the case of cyanocinnamic acid esters the reaction was accompanied by intramolecular acylation at N(5) to give 1-aryl-3,9-dioxo-3H,9H,11H-benzo[5,6][1,8]naphthyridino[1,8-ab]quinazoline-2-carbonitrile.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.11, 1698–1708, November 2007. 相似文献
13.
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
14.
2-(2-Furyl)-1-methyl-1H-acenaphtho[9,10-d]imidazole was obtained by the condensation of 9,1-acenaphthenequinone with furfural
in the presence of ammonium acetate followed by N-methylation of the obtained 2-(2-furyl)-1H-acenaphtho[9,10-d]imidazole with
methyl iodide in N-methylpyrrolid-2-one in the presence of potassium hydroxide. It was established that its electrophilic
substitution in an acidic medium only takes place at position 2 of the furan ring while in a neutral medium both position
2 and position 7 of the aromatic part of the molecule undergo electrophilic attack.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 191–196, February, 2006. 相似文献
15.
V. Bobošík A. Krutošíková U. Jordis 《Monatshefte für Chemie / Chemical Monthly》1995,126(6-7):747-752
Summary A number of substituted 2,3-dimethylfuro[3,2-c]pyridines was synthesized. 3-(4,5-Dimethyl-2-furyl)propenoic acid (1) was converted to the acid azide2, which in turn was cyclized to give 2,3-dimethyl-5H-furo[3,2-c]pyridine-4-one (3) by heating at 240°C in Dowtherm. The pyridone3 was chlorinated with phosphorus oxychloride to give4, which was reduced with zinc and acetic acid to 2,3-dimethylfuro[3,2-c]pyridine (5). Treatment of4 with several secondary heterocyclic amines led to compounds6a–6c. Reaction of pyridone3 with phosphorus pentasulfide rendered the thione7, which was methylated to8a. The 4-methoxy derivative8b was obtained from4 with sodium methoxide. 2,3,5-Trimethylfuro[3,2-c]pyridine-4-one (9) was obtained by reaction of3 with methyl iodide.Dedicated to Professor Dr.Fritz Sauter on the occasion of his 65th birthday 相似文献
16.
Cyclocondensation of N-prop-2-ynyl-o-phenylenediamine with phenyl isothiocyanate leads to the formation of 1-(3-arylprop-2-ynyl)-2,3-dihydro-1H-benzimidazole-2-thiones.
In the reactions of diacetylene derivatives — N-penta-2,4-diynyl-o-phenylenediamine — with phenyl isothiocyanate the formation
of two heterocyclic nuclei occurs simultaneously to form [1,3]thiazolidino[3,2-a]benzimidazoles.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, 627–631, April, 2007. 相似文献
17.
A. A. Bogolyubov N. B. Chernysheva V. V. Semenov 《Chemistry of Heterocyclic Compounds》2004,40(9):1124-1130
4-(Bromomethylene)-5,5-dimethyl-1,3-dioxolan-2-one was obtained on the basis of the readily obtainable 4-methylene-5,5-dimethyl-1,3-dioxolan-2-one. It forms 2-imidazo[1,2-a]pyridin-2-yl-2-propanol with 2-aminopyridine, 11a-hydroxy-1,1-dimethyl-3-oxo-1,5,11,11a-tetrahydro[1,3]oxazolo[3,4-a]pyrido[1,2-d]-10-pyrazinium bromide with 2-(aminomethyl)pyridine, and the corresponding derivative of 4-hydroxyoxazolidin-2-one with 2-(3,4-dimethoxyphenyl)ethylamine. The last product was converted by intramolecular amidoalkylation without isolation into 10b-(bromomethyl)-8,9-dimethoxy-1,1-dimethyl-1,5,6,10b-tetrahydro[1,3]oxazolo[3,4-a]isoquinolin-3-one. 相似文献
18.
T. I. Yaroshenko A. S. Nakhmanovich L. I. Larina V. N. Elokhina S. V. Amosova 《Chemistry of Heterocyclic Compounds》2008,44(9):1129-1134
Interaction of benzimidazole-2-thione with propargyl bromide under found conditions permitted the direct synthesis of 2-(2-propynylsulfanyl)-3H-1,3-benzimidazolium
bromide, the base 2-(2-propynylsulfanyl)-1H-1,3-benzimidazole, stable crystalline 2-(1,2-propadienylsulfanyl)-1H-1,3-benzimidazole,
and 3-methyl[1,3]thiazolo[3,2-a][1,3]benzimidazole. The reaction of benzimidazole-2-thione with 1,3-dibromopropyne in chloroform
or absolute methanol gave 2-(3-bromo-2-propynylsulfanyl)-3H-1,3-benzimidazolium bromide, and in absolute methanole in the
presence of a twofold excess of sodium methoxide the reaction proceeded stereo-and regioselectively to give 3-[(Z)-bromomethylidene][1,3]thiazolo[3,2-a][1,3]benzimidazole.
Presented to Academician B. A. Trofimov on his 70th jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, 1399–1405, September, 2008. 相似文献
19.
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
20.
The reaction of 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one with carbonyl compounds occurs at the C(6) and/or N(5) atoms depending on the nature of the reagent and the conditions. Condensation with aldehydes gives 6-arylidene-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones.
Acylation using acid anhydrides or acid chlorides gave 5-acyl-, 6-acyl-, and 5,6-diacyl-5,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones
depending again on the reaction conditions. Acylation using chloroacetyl chloride is accompanied by an intramolecular alkylation
to give 7H,8H-2a, 7a-diaza-cyclopenta[f,g]naphthacene-1,7(2H)-dione. Phenyl isocyanate gave the derivative containing a CONHPh
group at position 6.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1509–1520, October, 2007. 相似文献