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1.
S. Yu. Ryabova L. M. Alekseeva N. A. Rastorgueva E. A. Lisitsa D. M. Papakhin V. A. Parshin V. G. Granik 《Russian Chemical Bulletin》2006,55(12):2278-2284
Reactions of 3-[(N-aryl-N-chloroacetyl)amino]-2-formylindoles with substituted anilines gave 1,4-diaryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indol-4-ium chlorides and those with 4-aminopyridine yielded 4-amino-1-(1-aryl-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indol-3-yl)pyridinium chlorides. Reduction of 1,2,3,6-tetrahydrodiazepinoindol-4-ium chlorides afforded the corresponding
hexahydro derivatives. An alternative synthesis of 1-(4-nitrophenyl)-3-oxo-4-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole from 3-[N-(4-nitrophenyl)amino]-2-[(phenylimino)methyl]indole was developed. The method involves the following sequence of transformations:
reduction, chloroacetylation, and intramolecular alkylation.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2193–2199, December, 2006. 相似文献
2.
J. A. Van Allan G. A. Reynolds D. P. Maier S. Chie Chang 《Journal of heterocyclic chemistry》1972,9(6):1229-1233
The iminium salt, N,N-dimethyl-N-[2-(2,6-diphenyl-4H-pyran-4-ylidene)ethylidene]iminium perolilorate ( 1 ), reacts with secondary amines, such as piperidine, by exchanging the dimethyl-amino function for a piperidine. Primary amines react with 1 to give 1-alkyl-2-phenyl-4-phenacylidene-1,4-dihydropyridines. The bisiminium salt, N,N,N',N' -tetramethyI-N,N'-[2-(2,6-diphenyl-4H-pyran-4-ylidene)-1,3-propanediylidene]bis(iminium perchlorate) ( 2 ), reacts with ammonia to give 3,6-diphenylcopyrine and with primary amines to give the corresponding N,N' -dialkyl quaternary copyrines. The salt 2 reacts with secondary amines with exchange of the dimethylamino groups of 2 by the secondary arnine and addition of the amine at the 2-position of the pyran ring. 相似文献
3.
I. E. Tolpygin V. P. Rybalkin E. N. Shepelenko L. L. Popova Yu. V. Revinskii A. V. Tsukanov O. I. Dmitrieva A. D. Dubonosov V. A. Bren’ V. I. Minkin 《Russian Journal of Organic Chemistry》2008,44(4):557-560
A number of N-(9-antrylmethyl)-N′-arylmethylidenebenzene-1,2-diamines and 1-(9-anthrylmethyl)-2-aryl-1H-benzimidazoles were synthesized by condensation of N-(9-anthrylmethyl)benzene-1,2-diamine with aromatic and heterocyclic aldehydes. Study on their luminescent properties and complexing ability showed that 2-{[2-(9-anthrylmethylamino)phenylimino]methyl}-5-methylphenol, 2-{[2-(9-anthrylmethylamino)phenylimino] methyl}-4-methoxyphenol, and 2-{[2-(9-anthrylmethylamino)phenylimino]methyl}-6-methoxy-4-nitrophenol are effective and highly selective chemosensors for H+ and Hg2+ ions. 相似文献
4.
Kurbatov S. V. Kuznetsov D. N. Simakov V. I. Voronina V. A. Zhdanov Yu. A. Olekhnovich L. P. 《Russian Journal of General Chemistry》2004,74(5):731-737
Alkylation of o-(N-sulfonylamino)phenylimino derivatives of indol-2-one and cyclohepta[c]furan with phenacyl bromides is accompanied by cyclization to previously unknown tetrahydroquinoxalines having spiro-fused oxoindole and cyclohepta[c]furan fragments. The structure of the latter includes a nitrogen-oxygen triangular system typical of most natural cytotoxic compounds. 相似文献
5.
Monireh Heshmati Gonbari Ali Ramazani Ali Souldozi 《Phosphorus, sulfur, and silicon and the related elements》2013,188(2):309-314
N, N′ -diphenylthiourea reacts with dialkyl acetylenedicarboxylates in acetone to form 1:1 adducts, which undergo a cyclization reaction to produce alkyl (Z)-2-[4-oxo-3-phenyl-2-(phenylimino)-1,3-thiazolan-5-yliden]acetates in fairly good yields. NMR spectra indicated that the reaction is completely stereoselective. 相似文献
6.
I. E. Tolpygin E. N. Shepelenko Yu. V. Revinskii A. V. Tsukanov A. D. Dubonosov V. A. Bren’ V. I. Minkin 《Russian Journal of Organic Chemistry》2009,45(2):161-165
A series of N-(9-anthrylmethyl)arylimines was prepared by condensation of N-(2-aminophenyl)-N-(9-anthrylmethyl)amine with aromatic aldehydes. The study of the luminescent and complexing properties of compounds obtained showed that 2-{[2-(9-anthrylmethylamino)phenylimino]methyl}-1-naphthol and 1-{[2-(9- anthrylmethylamino)phenylimino]methyl}-6-bromo-2-naphthol were efficient highly selective chemosensors of cations Hg2+. 相似文献
7.
Giuseppe Daidone Salvatore Plescia Jole Fabra 《Journal of heterocyclic chemistry》1980,17(7):1409-1411
Thermal decomposition of the diazonium sulfate derived from N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-aminobenzamide afforded products formulated as 1-phenyl-3-methyl[2]benzopyrano[4,3-c]pyrazol-5-one (yield 10%), 1,4-dimethyl-3-phenylpyrazolo[3,4-c]isoquinolin-5-one (yield 10%), N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-hydroxybenzamide (yield 8%) and 4′-hydroxy-2,3′-dimethyl-1′-phenylspiro[isoindoline-1,5′-[2]-pyrazolin]-3-one (yield 20%). Decomposition of the diazonium sulfate derived from N-methyl-(1,3-diphenylpyrazol-5-yl)-2-aminobenzamide gave products formulated as 7,9-dimethyldibenzo[e,g]pyrazolo[1,5-a][1,3]-diazocin-10-(9H)one (yield 8%), 4-methyl-1,3-diphenylpyrazolo[3,4-c]isoquinolin-5-one (yield 7%) and 4′-hydroxy-2-methyl-1′,3′-diphenylspiro[isoindoline-1,5′-[2]pyrazolin]3-one (yield 10%). The spiro compounds 6a,b underwent thermal and acid-catalysed conversion into the hitherto unknown 2-benzopyrano[4,3-c]pyrazole ring system 7a,b in good yield. Analytical and spectral data are presented which supported the structures proposed. 相似文献
8.
A series of novel complexes of the type Cu(II)(Ln)2(H2O)2]•xH2O [where Ln = L 1–4 , these ligands being described as: L 1 , 2‐({4‐[6,7‐dihydrothieno[3,2‐c]pyridin‐5(4H)‐ylsulfonyl]phenylimino}methyl)phenol, x = 1; L 2 , 2‐({4‐[6,7‐dihydrothieno[3,2‐c] pyridin‐5(4H)‐ylsulfonyl]phenylimino}methyl)‐5‐(methoxy)phenol, x = 2; L 3 , 5‐chloro‐2‐({4‐[6,7‐dihydrothieno[3,2‐c]pyridin‐5(4H)‐ylsulfonyl]phenylimino}methyl)phenol, x = 2; and L 4 , 5‐bromo‐4‐chloro‐2‐({4‐[6,7‐dihydrothieno[3,2‐c]pyridin‐5(4H)‐ylsulfonyl]phenylimino} methyl)phenol, x = 1] was investigated. They were characterized by elemental analysis, IR, 1H‐NMR, 13C‐NMR and electronic spectra, magnetic measurements and thermal studies. The FAB‐mass spectrum of [Cu(II)( L 1 )2(H2O)2]•H2O was determined. A magnetic moment and reflectance spectral study revealed that an octahedral geometry could be assigned to all the prepared complexes. Ligands (Ln) and their metal complexes were screened for their in vitro antibacterial activity against Bacillus subtillis, Pseudomonas aeruginosa, Escherichia coli and Serratia marcescens bacterial strains. Kinetic parameters such as order of reaction (n), the energy of activation (Ea), the pre‐exponential factor (A), the activation entropy (ΔS≠), the activation enthalpy (ΔH≠) and the free energy of activation (ΔG≠) are reported. Copyright © 2011 John Wiley & Sons, Ltd. 相似文献
9.
Fredy R. Prez Julio Belmar Claudio Jimnez Yanko Moreno Patricio Hermosilla Ricardo Baggio 《Acta Crystallographica. Section C, Structural Chemistry》2005,61(6):m318-m320
The title compound, [Cu(C19H26N3O)2], is the first reported complex of the alkylpyrazolone‐derived ligand 1‐n‐hexyl‐3‐methyl‐4‐[1‐(phenylimino)propyl]‐1H‐pyrazol‐5(4H)‐one. The most notable feature is the imine–enol character presented by the ligand due to coordination, in spite of its enamine–ketone structure in the free state. The ligand chelates through N and O atoms, resulting in a square‐planar coordination around the CuII atom, which lies on an inversion centre. 相似文献
10.
Jasmina S. Brbori? Sote Vladimirov Mirjana S. Jovanovi? Nikola Dogovi? 《Monatshefte für Chemie / Chemical Monthly》2004,28(11):1009-1014
The synthesis and characterization of N-[2-[[4-iodo-2,6-bis(1-methylethyl)phenyl]amino]-2-oxoethyl]-N-(carboxymethyl)glycine and N-[2-[(4-iodo-2,6-diethylphenyl)amino]-2-oxoethyl]-N-(carboxymethyl)glycine is presented, as well as a modified and improved synthesis of N-[2-[(2,4-diiodo-6-methylphenyl)amino]-2-oxoethyl]-N-(carboxymethyl)glycine. These compounds are new agents for hepatobiliary imaging. 相似文献
11.
Acyl-and Alkylidenephosphines. XXVI. 2, 4-Bis (phenylimino)-1, 3-diphosphetanes from Thiocarbamoyl- and Carbamoyltrimethylsilylphosphines . Bis(trimethylsilyl)phosphines R? P[? Si(CH3)3]2 1 (R = H3C a, H5C6 b, (H3C)3C e, H11C9 d) and phenyl isothiocyanate give insertion compounds which were identified as [CN-phenyl, N-trimethylsilyl)thiocarbamoyl]trimethylsilylphosphines 3 ? 2 in solution as well as in the solid state [2]. In the presence of small amounts of solid sodium hydroxide the phenyl derivative 3 ? 2b eliminates bis(trimethylsilyl) sulfane, whereas the tert-butyl 3 ? 2c and the mesityl compound 3 ? 2d show the same reaction even without a catalyst. The unstable [(phenylimino)methylidene]phosphines 6 formed first, dimerize rapidly to give 2, 4-bis(phenylimino)-1,3-diphosphetanes 7 which in solution exist as mixtures of the E and Z isomers. Via a NaOH-catalyzed elimination of hexamethyldisiloxane these cyclic phosphines 7 can also be obtained from the adducts of phenyl isocyanate and bis(trimethylsilyl)phosphines 1. Taking the thermally sufficiently stable tert-butyl derivative 7 c as an example, the temperature dependence of n.m.r. spectra is discussed in detail. 相似文献
12.
Summary. The synthesis and characterization of N-[2-[[4-iodo-2,6-bis(1-methylethyl)phenyl]amino]-2-oxoethyl]-N-(carboxymethyl)glycine and N-[2-[(4-iodo-2,6-diethylphenyl)amino]-2-oxoethyl]-N-(carboxymethyl)glycine is presented, as well as a modified and improved synthesis of N-[2-[(2,4-diiodo-6-methylphenyl)amino]-2-oxoethyl]-N-(carboxymethyl)glycine. These compounds are new agents for hepatobiliary imaging. 相似文献
13.
Secondary penta-2,4-diynylamines were synthesized, and their pK
a(MeOH) values were obtained by means of nonaqueous potentiometric titration. The reactions of the amines with phenyl isothiocyanate, leading to 2-(phenylimino)-5-(prop-2-ynilidene)thiazolidines, were studied. The N-butyl- and N-benzylthiazolidines with alkyl substituents at the triple bond, formed by the reactions, undergo autooxidation into thiazolidin-4-ones. 相似文献
14.
The penta-glutamyl derivative of N-[4-[N-[3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]-benzoyl)-L-glutamic acid (1, 5-DACTHF, 543U76) was synthesized by a convergent route. L-γ-Glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamic acid heptakis t-butyl ester ( 20 ) was prepared in ten steps from L-glutamic acid di-t-butyl ester and N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester. 4-[N-[3-(2,4-Diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]trifluoroacetamido]benzoic acid ( 6 ), which was synthesized from pyrimidinylpropionaldehyde 3 in three steps, was condensed with 20 , followed by deprotection to provide N-[4-[N-[3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]benzoyl]-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamic acid ( 2 ). Hexaglutamate 2 is a potent inhibitor of glycinamide ribonucleotide transformylase. 相似文献
15.
█tl="American"█The synthesis of the three N,N′-di(4-coumaroyl)tetramines, i.e., of (E,E)-N-{3-[(2-aminoethyl)amino]propyl}-3,3′-bis(4-hydroxyphenyl)-N,N′-(ethane-1,2-diyl)bis[prop-2-enamide] ( 1a ), (E,E)-N-{4-[(2-aminoethyl)amino]butyl}-3,3′-bis(4-hydroxyphenyl)-N,N′-(ethane-1,2-diyl)bis[prop-2-enamide] ( 1b ), and (E,E)-N-{6-[(2-aminoethyl)amino]hexyl}-3,3′-bis(4-hydroxyphenyl)-N,N′-(ethane-1,2-diyl)bis[prop-2-enamide] ( 1c ), is described. It proceeds through stepwise construction of the symmetric polyamine backbone including protection and deprotection steps of the amino functions. Their behavior on TLC in comparison with that of 1,4-di(4-coumaroyl)spermine (=(E,E)-N-{4-[(3-aminopropyl)amino]butyl}-3,3′-bis(4-hydroxyphenyl)-N,N′-(propane-1,3-diyl)bis[prop-2-enamide]; 2 ) is discussed. 相似文献
16.
Abstract Three novel dicarboxylic acids, bis-4,4′-[N-4(4′-hydroxycarbonyl phenyleneoxy) phthalimido] diphenyl sulfone, bis-4,4′-[N-4(4′-hydroxycarbonyl phenyleneoxy) phthalimido] diphenyl methane, and bis-4,4′-[N-4(4′-hydroxycarbonyl phenyleneoxy) phthalimido] diphenyl ether, were synthesized, and several polyesterimides were prepared from diacid chlorides and bisphenols by solution polycondensation. The polymers were obtained in 65–88% yield and had inherent viscosities in the 0.18 to 0.64 dL/g range. The polymers were characterized by IR, elemental analysis, x-ray, TGA, DSC, and solubility tests. All the polymers were readily soluble in polar aprotic solvents and had a 10% weight loss temperature above 375°C in nitrogen. 相似文献
17.
Srihari Kusuma W. David Wilson David W. Boykin 《Journal of heterocyclic chemistry》1985,22(5):1229-1232
A series of five 8-substituted α-[bis(2-hydroxyethyi)aminoethyl]naphtho[2,1-b]thiophenes 7 and a series of seven N-(3-dimethylaminopropyl)-8-substituted naphtho[2,1-b]thiophene-4-carboxamides 8 have been synthesized. The naphtho[2,1-b]thiophene-4-carboxylic acids 4 were prepared by photooxidative cyclization of α-(2-thienyi)-β-arylacrylic acids 3. The carboxylic acids 4 were converted by a conventional five step route involving α-bromoketone intermediates to the a-[bis(2-hydroxyethyl)aminomethyl]-8-substituted naphtho-[2,1-6]thiophene-4-methanols 7 and by a standard two-step amide preparation to the N-(3-dimethylaminopropyl)-8-substituted naphtho[2,1-6]thiophene-4-carboxamides 8 . 相似文献
18.
The preparation of isonipecotinoyl analogues of aminopterin and methotrexate is described. Condensation of diethyl N-isonipecotinoyl-L-glutamate 4 with 2-amino-5-bromomethyl-3-cyanopyrazine 5 afforded diethyl N-(N-[(2-amino-3-cyanopyrazin-5-yl)methyl]isonipecotinoyl)-L-glutamate 6 . Cyclisation of 6 with guanidine followed by blocking group hydrolysis afforded N-([N-(2,4-diaminopteridin-6-yl)methyl]isonipecotinoyl)-L-glutamic acid 8 . Coupling of N-(2-amino-4(3H)ioxopteridin-6-yl]methyl)isonipecotinic acid 11 with diethyl L-glutamate gave diethyl N-[(N-[2-amino-4(3H)-oxopteridin-6-yl]methyl)isonipecotinoyl]-L-glutamate 12 . Blocking group hydrolysis afforded N-[(N-[2-amino-4(3H)-oxopteridin-6-yl]methyl)isonipecotinoyl]-L-glutamic acid 13 . 相似文献
19.
G. A. Brine D. K. Sawyer P.-T. Huang P. A. Stark K. D. Gaetano F. I. Carroll 《Journal of heterocyclic chemistry》1992,29(7):1773-1779
Treatment of (±)-cis-N-(3-methyl-4-piperidyl)-N-phenylpropanamide (2) with styrene oxide (1) yielded a mixture of (±)-cis-N-[1-(2-hydroxy-2-phenylethyl)-3-methyl-4-piperidyl]-N-phenylpropanamide (3) and (±)-cis-N-[1-(2-hydroxy-1-phenylethyl)-3-methyl-4-piperidyl]-N-phenylpropanamide (4) . The structure of compound 3 was confirmed by an unambiguous synthesis via (±)-cis-N-[1-(2-oxo-2-phenylethyl)-3-methyl-4-piperidyl]-N-phenylpropanamide (6) . The proton and carbon-13 resonances of compounds 3 and 4 were assigned with the aid of two-dimensional heteronuclear correlation experiments. 相似文献
20.
Simonov A. Yu. Lakatosh S. A. Luzikov Yu. N. Reznikova M. I. Preobrazhenskaya M. N. 《Russian Chemical Bulletin》2010,59(7):1442-1450
A dialkylaminomethylation reaction (the Mannich reaction) of 3,4-bis(indol-l-yl)-maleimides and 3-(indol-l-yl)-4-(indolin-l-yl)maleimides
leads to mono- and di(dimethyl-amino) derivatives at position 3 of one or two indole rings. A series of 3,4-bis(indol-l-yl)-maleimides
and 3-(indol-l-yl)-4-(indolin-l-yl)maleimides containing ω-hydroxyalkyloxy-methyl substituents at position 3 of the indole
ring was obtained by the reaction of iodomethyl-ates of these compounds with ethylene glycol and other 6h,ω-alkanediols. The
reaction of quaternary salts of bis(3-dimethylaminomethylindol-l-yl)maleimides with 6h,ω-alkanediols resulted in the isolation
of 3,4-bis(3-ω-hydroxyalkyloxymethylindol-l-yl)maleimides. Upon heating iodomethylate of 3-(3-dimethylaminoindol-l-yl)-4-(indolin-l-yl)maleimide
in pyridine, 5,6-dihydro-10-methyl-H-indolo[l′,7a′,7′:4,5,6]pyrrolo[3′,4′:2,3]-[l,4]diazepino[l,7-a]-indole-l,3(2H)-dione was obtained due to the intramolecular alkylation and formation of the bond between position 2 of the
indole and position 7 of the indoline rings. 相似文献