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1.
Konovalova V. V. Shklyaev Yu. V. Maslivets A. N. 《Russian Journal of Organic Chemistry》2011,47(7):1119-1120
Russian Journal of Organic Chemistry - 相似文献
2.
Krystyna Bogdanowicz-Szwed Artur Budzowski Regina Gil Pawe? Serda 《Monatshefte für Chemie / Chemical Monthly》2010,57(7):63-74
Abstract
The new thioamides 2-oxoindane-1-carbothioamides and 2-oxo-1,2,3,4-tetrahydronaphthalene-1-carbothioamides underwent conjugated addition to (E)-β-nitrostyrenes followed by cyclization to give products containing 5-hydroxyimino-2-aryliminothiophene rings spiro-annulated to the 2-indanone or 2-tetralone system. On treatment with hydrochloric acid in boiling methanol the compounds underwent a new rearrangement, involving transformation of the 2-aryliminothiophene ring to a pyrrole and an opening of the alicyclic ring in the proximity of the carbonyl group, affording 2-(1,3-diaryl-2-oxo-5-thioxopyrrol-4-yl)benzeneacetic or 2-(1,3-diaryl-2-oxo-5-thioxopyrrol-4-yl)benzenepropanoic acid methyl esters. The structures of two selected pyrrole derivatives were determined by X-ray crystal analyses. The thioamides derived from 2-indanone showed unexpected reactivity towards primary alcohols and underwent conversion to 2-hydroxy-1H-indene-3-thiocarboxylic acid O-esters. 相似文献3.
S. A. Pogosyan Dzh. A. Avakimyan H. M. Stepanyan 《Russian Journal of Organic Chemistry》2016,52(9):1308-1311
Methods have been developed for the synthesis of new heterocyclic systems, spiro[chromene-4,3′- indoles] and spiro[indole-3,4′-quinolines] by the base-catalyzed domino reaction of isatins with 5,5-dimethylcyclohexane- 1,3-dione (or 5,5-dimethyl-3-anilinocyclohex-2-en-1-one) and ethyl cyanoacetate. 相似文献
4.
Synthesis of new thiopyran fused spirooxindoles (spiro[indoline-3,4′-thiopyran]-2-ones) were achieved by a multicomponent reaction of N-methyl isatin, malononitrile/ethyl cyanoacetate, and β-oxodithioester using N,N′-dimethylaminopyridine as the catalyst. 相似文献
5.
V. A. Samsonov Yu. V. Gatilov V. A. Savel’ev S. S. Baranova 《Russian Journal of Organic Chemistry》2012,48(3):399-410
Reactions of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with aliphatic amines and sodium hydroxide resulted
in removal of one N-oxide oxygen atom and formation of 4-alkylamino- or 4-hydroxy-substituted 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1-oxides,
respectively. The title compound reacted with ammonia and methylamine in the presence of MnO2 with conservation of both N-oxide moieties, and the products were 4-amino- and 4-methylamino-5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxides.
The reactions with aromatic amines were accompanied by removal of both N-oxide oxygen atoms with formation of N-aryl-5-nitrospiro[benzimidazole-2,1′-cyclohexane]-4-amines. In the reactions of 5-nitrospiro-[benzimidazole-2,1′-cyclohexane]
1,3-dioxide with sodium azide and aromatic amine hydrochlorides nucleophilic replacement of the 5-nitro group by azido or
arylamino occurred, in the first case both N-oxide fragments being conserved. The reactions with aromatic amine hydrochlorides afforded N-aryl-5-nitrospiro[benzimidazole-2,1′-cyclohexan]-4-amine 1-oxides. Treatment of 5-nitrospiro[benzimidazole-2,1′-cyclohexane]
1,3-dioxide with sodium cyanide led to the formation of 5-oxo-3,5-dihydrospiro[benzimidazole-2,1′-cyclohexane]-4-carbonitrile
1-oxide. 相似文献
6.
《Tetrahedron》2019,75(52):130775
A 1,3-dipolar cycloaddition reaction of arynes with 3-diazoindolin-2-ones under mild conditions in excellent yields has been developed, which allows facile access to a library of labile spiro[indazole-3,3′-indolin]-2′-ones. Spiro[indazole-3,3′-indolin]-2′-imines could be obtained as well following the same protocol. The isomerization reaction of spiro[indazole-3,3′-indolin]-2′-ones under thermal or acidic conditions has been efficiently achieved to afford a wide range of indazolo-[2,3-c]quinazolin-6(5H)-ones and the one-pot synthesis of indazolo-[2,3-c]quinazolin-6(5H)-ones from arynes and 3-diazoindolin-2-ones is also described. Whereas, spiro[indazole-3,3′-indolin]-2′-imines could not undergo the same rearrangement. 相似文献
7.
L. L. Zamigailo O. N. Petrova M. G. Shirobokova V. V. Lipson 《Russian Journal of Organic Chemistry》2013,49(2):288-293
Reactions of 4-oxo benz[1,3-e]oxazinium perchlorates with 1-R1-3-R2-5-aminopyrazoles lead to the formation of derivatives of pyrazolo[3,4-d]pyrimidine and pyrazolo[1,5-a]1,3,5]triazine series, and with 3-amino-1,2,4-triazole, to [1,2,4]triazolo[1,5-a][1,3,5]triazines. 相似文献
8.
H. M. Moustafa 《Phosphorus, sulfur, and silicon and the related elements》2013,188(7):1397-1412
2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's Reagent, LR, 1 ) reacts with cycloalkylidenecyanothioacetamides ( 2 and 3 ) to give 5'-cyano-2'-(4-methoxyphenyl)spiro [cyclopentane(cyclohexane)-1,6'-perhydro-[1,3,2]thiazaphosphixane]-2',4'-disulfide ( 4 and 5 ). The reaction of compounds 4 and 5 with f -halo compounds led to the formation of the substituted thio-compounds 6a-e and 7a-e , respectively, these compounds, upon treatment with sodium ethoxide, produce the corresponding thienothiazaphosphixine derivatives 8a-e and 9a-e respectively. Compounds 8a-e and 9a-e react with LR under different reaction conditions to give polyfused heterocyclic compounds 10a-d and 11a-d respectively. Treatment of compounds 8b and 9b with CS 2 and (CH 3 ) 2 SO 4 gave the corresponding dithiocarbamate methyl ester derivatives 12 and 13 , respectively, which on treating with hydrazine hydrate yielded compounds 14 and 15 respectively. Compounds 14 and 15 reacted with LR to yield compounds 16a , b and 17a , b respectively. 相似文献
9.
A. D. Khalaji A. Foroghnia K. Fejfarova M. Dusek 《Journal of Structural Chemistry》2013,54(4):774-778
The Schiff base compounds N,N′-bis(3,4-dimethoxybenzylidene)-2,2-dimethylpropane-1,3-diamine hydrate, (3,4-MeO-ba)2Mepn.H2O (1), and N,N′-bis(3,4-dimethoxybenzylidene)butane-1,4-diamine, (3,4-MeO-ba)2bn (2), with different central groups derived from 3,4-dimethoxybenzaldehyde are synthesized and characterized by elemental analysis, FT-IR and 1H NMR spectroscopy. The crystal structure of 1 is determined by single crystal X-ray diffraction. Each imino functional group (-C=N-) is coplanar with its adjacent benzene ring and the two benzene rings form a dihedral angle of 86.868(27)°. Title compound 1 crystallizes in the monoclinic space group P21/n with unit cell parameters: a = 9.0774(2) Å, b = 29.2138(5) Å, c = 8.5696(2) Å, β = 92.4756(14)°, V = 2270.41(8) Å3 and Z = 4. 相似文献
10.
Ya. S. Kayukov O. V. Kayukova E. S. Kalyagina I. N. Bardasov O. V. Ershov O. E. Nasakin V. A. Tafeenko 《Russian Journal of Organic Chemistry》2011,47(3):392-401
2′-Oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole]-2,2,3,3-tetracarbonitriles reacted with oxygencentered nucleophiles to form addition products at the cyano groups with conservation of the three-membered ring. Reactions of the title compounds with alcohols required the presence of base catalyst, and the products, 2-amino-4,4-dialkoxy-2′-oxo-1′,2′-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1,5-dicarbonitriles, were converted into the corresponding 2-imino-2′,4-dioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1,5-dicarbonitriles and 2,2′,4-trioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1,5-dicarbonitriles by the action of acetic and sulfuric acids, respectively. The reactions with ketone oximes occurred in the absence of a catalyst, yielding 2-amino-4,4-bis(alkylideneaminooxy)-2′-oxo-1′,2′-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1,5-dicarbonitriles. The reactions with thiols, aliphatic amines, and anilines were accompanied by opening of the three-membered ring. In the reactions with triphenylphosphine and thiols 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)malononitrile was obtained, while morpholine and N,N-dimethylaniline gave rise, respectively, to 3,3-diaryl-and 3,3-dimorpholino-1H-indol-2(3H)-ones and tri- and dicyanoethylene derivatives. 相似文献
11.
An efficient procedure for the synthesis of spiro[furan-3,3′-indolin]-2-ones and dispiro[cycloalkane-1,2′-furan-3′,3″-indolin]-2″-ones has been achieved in high yields and stereoselectivity by photoinduced electron transfer-catalyzed [3+2] reactions of substituted spiro[indoline-3,2′-oxiran]-2-ones with olefins. The reactions proceed by ring opening of spiro[indoline-3,2′-oxiran]-2-ones via Cβ–O bond cleavage and subsequent cycloaddition with olefins by using 2,4,6-triphenylpyrylium tetarfluoroborate (TPT) as a sensitizer. 相似文献
12.
A facile regio and stereoselective synthesis of novel spiro[indolin-3,2′-pyrrolidin]-2-one’s have been accomplished through 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the reaction of isatin and benzyl amine with quinoline bearing dipolarophiles in good yields. The synthesized compounds were well characterized through different spectroscopic techniques, such as single crystal XRD, FTIR, NMR, and mass spectral analysis. 相似文献
13.
Ivanov S. M. Mironovich L. M. Rodinovskaya L. A. Shestopalov A. M. 《Russian Chemical Bulletin》2017,66(6):1126-1130
Russian Chemical Bulletin - New pyrido[2′,3′:3,4]pyrazolo[5,1-c][1,2,4]triazin-4(6H)-one derivatives were synthesized from accessible 1,2,4-triazine and pyrazolo[5,1-c][1,2,4]triazine... 相似文献
14.
Sherif M. H. Sanad Mahmoud A. E. Hawass Ahmed A. M. Ahmed Mohamed A. A. Elneairy 《合成通讯》2018,48(14):1847-1856
4-(3-(4-Hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)-6-phenyl-2-thioxo-1,2-di hydro-pyridine-3-carbonitrile (1) reacted with ethyl chloroacetate (2) in ethanolic sodium acetate solution to yield the corresponding ethyl (3-cyanopyridin-2-ylsulphanyl)acetate derivative 3. Intramolecular cyclization of compound 3 was achieved by its heating in DMF containing potassium carbonate to afford the corresponding ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate derivative 4 which reacted with hydrazine hydrate in refluxing pyridine to yield the starting material 3-aminothieno[2,3-b]pyridine-2-carbohydrazide derivative 7. Compound 7 reacted with different reagents such as triethylorthoformate, formic acid, acetic acid and acetic anhydride to afford the target molecules pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-one derivatives 8–10, 12 and 13 in good to excellent yields. On the other hand, pyridine-2(1H)-thione derivative 1 reacted with hydrazine hydrate in refluxing pyridine to give the other starting material 3-amino-1H-pyrazolo[3,4-b]pyridine derivative 20 which reacted with acetylacetone under reflux to afford the target molecule pyrido[2′,3′:3,4]pyrazolo[1,5-a]-pyrimidine derivative 21 in a good yield. The structures of target molecules were elucidated using elemental analyses and spectral data. 相似文献
15.
Seyed Esmail Sadat-Ebrahimi Seyed Mohammad Haghayegh-Zavareh Saeed Bahadorikhalili Azadeh Yahya-Meymandi Mohammad Mahdavi 《合成通讯》2017,47(24):2324-2329
Cu(II)-β-cyclodextrin-catalyzed synthesis of spiro[indoline-3,4′-pyrano[3,2-c]chromene]-3′-carbonitriles through the reaction of isatin derivatives, 4-hydroxycoumarin, and malononitrile in ethanol at room temperature. 相似文献
16.
The reaction of the isomeric tetrachloro--, -, and -trifluoromethylpyridines and of 3,4,5-trichloro-2-trifluoromethylpyridine with sodium N,N-dimethyldithiocarbamate dihydrate has been studied. In the case of the -, and -isomers an intramolecular cyclization with the formation of 1,3-dithiol-2-one derivatives occurs and the remaining compounds give only products of mono- or disubstitution of chlorine atoms by a dithiocarbamate fragment at positions 4 or 6 of the pyridine ring. The structure of the compounds synthesized was proved using13C NMR and X-ray crystallographic analysis.See [6] for part 7.Institute of Chemical Physics, Chernogolovka, Russian Academy of Sciences, Chernogolovka 142432. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1278–1284, September, 1994. Original article submitted June 25, 1994. 相似文献
17.
V. M. Kisel' M. O. Platonov E. O. Kostyrko V. R. Kovtunenko 《Chemistry of Heterocyclic Compounds》2000,36(8):905-910
A method has been developed for the synthesis of 4-[2-(bromomethyl)phenyl] tetrahydro-2H-4-pyrancarbonitrile and a study was carried out on the reaction of this compound with primary amines, which, depending on the conditions, leads to either 4-[2-(R-aminomethyl)phenyl]tetrahydro-2H-4-pyrancarbonitriles or hydrobromides of 2-R-aryl-2,3,2,3,5,6-hexahydrospiro[isoquinoline-4(1H),4-pyran]-3-imines.Taras Shevchenko Kiev University, 252017 Kiev, Ukraine; e-mail: vkysil@mail.univ.kiev.ua. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1035–1041, August, 2000. 相似文献
18.
Rachid Bouhfid El Mokhtar Essassi Vincent Lequart Mohamed Massoui Patrick Martin 《合成通讯》2013,43(14):2096-2102
Novel spiro[1,4,2-dioxazole-5,3′-indolin]-2′-one derivatives were synthesized by 1,3-dipolar cycloaddition reactions of the isatin derivative with aryl nitrile oxide. The cycloadducts were characterized by spectral data including 1H NMR, 13C NMR, infrared, mass spectra, and elementary analysis. 相似文献
19.
N. S. Masterova L. M. Alekseeva A. S. Shashkov V. A. Tafeenko S. Yu. Ryabova V. G. Granik 《Russian Chemical Bulletin》2008,57(8):1765-1772
Alkylation of 11-benzyl-3,11-dihydro-4H-pyrimido[5′,4′:5,6]pyrido[3,2-b]indol-4-one with methyl iodide and methyl bromoacetate in DMF gave 3-alkylpyrimidopyridoindolones as the corresponding salts. The reaction in acetone in the presence of K2CO3 yielded 3,6-disubstitution products. Alkylation with DMF dimethyl acetal gave a mixture of the 3- and 6-alkylpyrimidopyridoindol-4-one bases. The structure of 4-oxo-4,6-dihydro-3H-pyrimido-[5′,4′:5,6]pyrido[3,2-b]indol-11-ium chloride (3b) was proved by X-ray diffraction analysis. 相似文献
20.
Longchen Cui Guodong Zhu Siyuan Liu Xiaoze Bao Xiangyu Zhao Jingping Qu Baomin Wang 《Tetrahedron》2018,74(19):2369-2375
An organic base-catalyzed 1,3-dipolar cycloaddition between 2-alkenylindolenines and azomethine ylides derived from isatins and benzylamines was successfully developed to assemble indolenine-substituted spiro [pyrrolidine-2,3′-oxindole] ring systems. Generally, good regioselectivities (up to 14:1 rr) and high yields (up to 91%) were obtained under mild conditions. 相似文献