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1.
The geometric parameters, the charge distribution, and the energetics of N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)-and N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimides and their conjugated acids were studied by density functional theory calculations
at the B3LYP/6-31G(d) level. The mechanism of the tandem hydride transfer/cyclization sequence, which occurs after protonation
of N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)-and N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimides, was analyzed. The investigation of the potential energy surface for the tandem hydride
transfer/cyclization of the iminium cation that formed upon protonation revealed that the hydride transfer followed by intramolecular
cyclization at position 7 of the indole fragment in N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)maleimide is the preferable process, unlike alternative intramolecular cyclization involving
the cationic center at the C(2) atom of the indole fragment and the benzene ring of the N-ethylaniline fragment of the indoleninium cation in N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimide. A study of the key intermediates of the assumed reaction mechanism demonstrated that
these intermediates are actually stationary points on the potential energy surface (minima and transition states).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2069–2073, December, 2006. 相似文献
2.
N-[2(3)-Hydroxyalkylj-4-thiazolidinones have been synthesized by the reaction of 2(3)-vinyloxyalkylamines with mercaptoacetic acid in 24–69 % yield. The structure of the compounds obtained was supported by (R and1H NMR spectroscopic data.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 677–679, March, 1996. 相似文献
3.
S. Yu. Ryabova L. M. Alekseeva E. A. Lisitsa V. G. Granik 《Russian Chemical Bulletin》2006,55(7):1248-1254
3-Arylamino-2-formylindoles were converted into oximes and then acetylated to give the corresponding O-acetyl derivatives. Chloroacetylation of the latter was accompanied by elimination of acetic acid, yielding 3-(N-aryl-N-chloroacetyl)amino-2-cyanoindoles. When heated in pyridine, these nitriles underwent cyclization into novel δ-carboline derivatives:
4-amino-1-aryl-2-oxo-1,2-dihydropyrido[3,2-b]indol-3-yl)pyridinium chlorides. The structures of the compounds obtained were proved by IR and 1H NMR spectroscopy and mass spectrometry.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1201—1207, July, 2006. 相似文献
4.
A new method for the synthesis of N-substituted 2-(4-oxo-4,5,6,7-tetrahydroindol-3-yl)acetic acids was developed. Alkylation of cyclic 1,3-diketones with 3,5,5,5-tetrachloropentan-2-one affords 1,4-diketones, which undergo cyclization with different primary amines into N-substituted 3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydroindol-4-ones. Acid hydrolysis of the latter gives the corresponding indol-3-ylacetic acids. The structures of the compounds obtained were confirmed by 1H and 13C NMR data. 相似文献
5.
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
6.
(Chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones have been obtained in good yields from 3-formylchromones on reaction with indoles and N-methylpyrrole under solvent-free conditions. 相似文献
7.
S. Yu. Ryabova N. A. Rastorgueva E. A. Lisitsa L. M. Alekseeva V. G. Granik 《Russian Chemical Bulletin》2003,52(6):1386-1398
A number of 1-aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole 4-oxides were synthesized based on 3-[N-aryl-N-(chloroacetyl)amino]-2-formylindoles. The nature of the substituent in the 1-aryl fragment has a pronounced influence on the course of reactions throughout the whole sequence of transformations during the synthesis of diazepinoindoles. The reduction of 4-oxides by formamidinosulfinic acid, hydrogen in the presence of Pd/C, and sodium bisulfite was studied. The structures of the reaction products were confirmed using IR and 1H NMR spectroscopy and mass spectrometry. 相似文献
8.
B. S. Fedorov N. I. Golovina V. V. Arakcheeva M. A. Fadeev G. V. Strukov V. V. Kedrov G. V. Shilov L. O. Atovmyan 《Russian Chemical Bulletin》1999,48(8):1584-1586
The reaction ofN,N′-bis(2-nitroxyethyl)pyridine-2,6-dicarboxamide with PdCl2 afforded previously unknowncis-(N-2-nitroxyethylpicolinamide-N,N′)dichloropalladium(II) andcis-[2-(2-pyridyl)-2-oxazoline-N,N′]dichloropalladium(II), which were isolated as a cocrystallizate of the molecular compounds. Its structure was established
by X-ray diffraction analysis.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1604–1606, August, 1999. 相似文献
9.
V. Yu. Korotaev Yu. A. Skorik A. Yu. Barkov M. I. Kodess A. Ya. Zapevalov 《Russian Chemical Bulletin》2005,54(11):2545-2549
3,3,3-Trifluoro-N′-(3-trifluoromethylphenyl)-1,2-propanediamine (5) was synthesized by the reaction of 2-diazo-1,1,1-trifluoro-3-nitropropane or 3,3,3-trifluoro-1-nitropropene with 3-aminobenzotrifluoride
followed by the reduction of the nitro group. The Michael 1,4-addition of diamine 5 to acrylic acid occurs only at the N(1) atom and affords N-mono-or N,N-dicarboxyethyl derivatives 6 and 7, depending on the reactant ratio. Protolytic equilibria 5–7 in aqueous solutions were studied by pH-potentiometry and UV spectroscopy. Only the aliphatic amino group can be protonated
in an aqueous solution, while the aromatic amino group remains unprotonated even in 12 M HCl. The stability constants of transition metal (Cu2+, Ni2+, Zn2+) complexes with ligands 5–7 were determined by pH-potentiometric titration. The stability of the complexes and selectivity of the ligands toward Cu2+ ions increase with an increase in the number of N-carboxyethyl groups.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2465–2469, November, 2005. 相似文献
10.
A. G. Mustafin A. R. Gimadieva I. N. Khalilov L. V. Spirikhin A. A. Fatykhov R. A. Nurushev I. B. Abdrakhmanov G. A. Tolstikov 《Russian Chemical Bulletin》1998,47(1):188-190
The effect ofmeta-substituents in the aromatic ring on the route of Claisen rearrangement ofN-(pent-3-en-2-yl)-3-fluoro(or 3-trifluoromethyl, 3,4-difluoro)anilines induced by ZnCl2 was investigated. The formation of two possibleortho-alkenylated reaction products was observed. The ratio of these isomers depends on the nature of the acid catalyst.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 188–190, January, 1998. 相似文献
11.
V. A. Tartakovsky A. S. Ermakov Yu. A. Strelenko D. B. Vinogradov S. A. Serkov 《Russian Chemical Bulletin》2001,50(5):911-913
A method was developed for the preparation of functionally substituted N-nitrooxazolidines and N-nitrotetrahydro-1,3-oxazines by nitration of the products obtained in the reactions of N-(2-hydroxyalkyl)- and N-(3-hydroxyalkyl)sulfamates with formaldehyde. 相似文献
12.
B. F. Kukharev 《Russian Chemical Bulletin》1997,46(8):1482-1483
Heating cyclohexanespiro-2-oxazolidine at 160–200°C in the presence of protic acids results in its decomposition to giveN-(2-hydroxyethyl)cyclohexylamine,N-(2-hydroxyethyl)-4,5,6,7-tetrahydroindole, and 2-cyclohexylidenecyclohexanone. The possible pathways leading to these compounds
are discussed.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1547–1548, August, 1997. 相似文献
13.
The reaction of 2-(4,5-dihydrofur-3-yl)-1,3-diphenyl-1,3-diaza-2λ3-phospholidine withC,N-diphenylnitrilimine is a multistage process, in the course of which the 1,2,4-diazaphosphorine ring is formed and both rings
of the initial organophosphorus compound are cleaved. 5-(2-Chloroethyl)-4-(N,N′-diphenylethylenediamino)-1,3-diphenyl-1,4-dihydro-1, 2,4λ5-diazaphosphorine was obtained as the final product.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 125–128, January, 2000. 相似文献
14.
N-(3-Azido-2-nitroxypropyl)-N-alkylnitramines andN-(2,3-diazidopropyl)-N-alkylnitramines were prepared by nitration and azidation ofN-alkyl-N-(2-hydroxy-3-chloropropyl)sulfamates andN-(3-azido-2-hydroxypropyl)-N-alkylsulfamates.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 206–208, January, 1999. 相似文献
15.
The reaction of 2-(4,5-dihydrofur-3-yl)-1,3-diphenyl-1,3-diaza-2λ3-phospholidine withC,N-diphenylnitrilimine is a multistage process, in the course of which the 1,2,4-diazaphosphorine ring is formed and both rings
of the initial organophosphorus compound are cleaved. 5-(2-Chloroethyl)-4-(N,N′-diphenylethylenediamino)-1,3-diphenyl-1,4-dihydro-1, 2,4λ5-diazaphosphorine was obtained as the final product.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 125–128, January, 2000. 相似文献
16.
A historical perspective on the application of conformational analysis to structure-based ligand design approach is presented. The application of isodensity molecular electrostatic potential surfaces with the conformational energy surfaces (CES) have allowed us to reach pertinent conclusions for aiding synthetic and biochemical studies. Here we illustrate such an application on the modeling of the potent analogs of an important, environmentally stringent herbicidal compound glyphosate by constructing conformational energy surfaces. The systems were modeled by substituting F, Cl, and NH— OH moiety to the position of pharmacophoric nitrogen center in glyphosate structure. All the calculations were thoroughly performed with ab initio MO theory at Hartree–Fock method using 3-21G(d) basis functions. On the basis of the results, we identified the bioactive conformations for N-fluoro-glyphosate, N-chloro-glyphosate, and N-hydroxyamino-glyphosate as (−38∘, 77∘), (−61∘, 111∘), and (−167∘, −169∘), respectively. Geometry optimization of certain selected conformations of these compounds using hybrid DFT method with 6–31+G(d) basis functions provides nearly equal values of φ and ψ. Moreover, the results indicate that the global minimum structures of N-fluoro and N-chloro analogs of glyphosate show cyclic conformation whereas the N-hydroxyamino-glyphosate global minimum structure shows spyrocyclic and zig-zag conformation. Also, the predicted bioactive conformation of N-hydroxyamino analog optimally overlaps with glyphosate backbone in EPSPS complex with 0.1 Å RMSD value. However, the other two compounds slightly deviate from the backbone of glyphosate with RMSD of 0.92 Å for N-fluoro-glyphosate and 0.83 Å for N-chloro-glyphosate. The linear N-hydroxyamino-glyphosate exhibits relatively more number of intermolecular hydrogen bond interactions as compared to the other two analogs. Further, comparison of CES of previously studied glyphosate analogs such as N-hydroxy-glyphosate (2.2 μM) and N-amino-glyphosate (0.61 μM) with the present systems reveals the order of activity as: N-hydroxyamino-glyphosate > N-fluoro-glyphosate > N-chloro-glyphosate based on CES flexibility. Also, the calculated heats of formation of N-fluoro-glyphosate, N-chloro-glyphosate, and N-hydroxyamino-glyphosate are −288, −209, and −288 kcal/mol, respectively, which clearly indicate that the N-hydroxyamino and N-fluoro analogs of glyphosate are thermodynamically more stable than N-amino-glyphosate (−278 kcal/mol). 相似文献
17.
K. A. Frolov V. V. Dotsenko S. G. Krivokolysko V. P. Litvinov 《Russian Chemical Bulletin》2005,54(5):1335-1336
Multicomponent cyclocondensation of Meldrum's acid, 2-chlorobenzaldehyde, and N-(4-bromophenyl)-3-amino-3-thioxopropanamide in the presence of N-methylmorpholine afforded N-methylmorpholinium 3-[N-(4-bromophenyl)carbamoyl]-4-(2-chlorophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate in 65% yield. When treated with
dilute HCl, the thiolate easily transformed into N-(4-bromophenyl)-4-(2-chlorophenyl)-2-oxo-6-thioxopiperidine-5-carboxamide, which reacted with alkyl halides to give products
of regioselective S-alkylation in high yields.
Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday.
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1297–1298, May, 2005. 相似文献
18.
Reactions of 2-(4,5-dihydro-3-furyl)-1,3-diphenyl-1,3-diaza-2λ3-phospholidine (1) with nitrile imines are multistep processes involving cleavage of one P-N bond of the diazaphospholidine ring to form substituted
5-(2-chloroethyl)-4-(N,N′-diphenylethylenediamino)-1,4-dihydro-1,2,4λ5-diazaphosphorines 4 as final products. Analogs of phospholidine 1, namely, 4,5-dihydro-3-furylphosphonous dipiperidide and dimorpholide, react with C,N-diphenylnitrile imine with retention of both P-N bonds to give 5-(2-hydroxyethyl)-1,2,4-diazaphosphorinium chlorides.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1590–1593, July, 2005. 相似文献
19.
ZHAO Chu-feng TANG Ming-sheng WANG Hong-ming WEI Dong-hui ZHAO Jing ZHANG Shou-ren CAO Shu-xia 《高等学校化学研究》2008,24(6):790-792
The reaction mechanisms of intermolecular cleavage reaction of N-(2-hydroxyphenyl)-phthalamic acid were studied via the density functional theory(DFT). All geometries of the reactant, transition states, and products were optimized at the B3LYP/6-31G(d, p) level. Vibration analysis was carried out to confirm its identity as transitions' structure, and the intrinsic reaction coordinate method(IRC) was used to search the minimum energy path. Two possible reaction channels are reported in this article. The calculated results indicate that O-cyclization reaction channel has the lower activation barrier, and therefore, it occurs more easier than the other. 相似文献
20.
Bożena Modzelewska-Banachiewicz Barbara Michalec Teresa Kamińska Liliana Mazur Anna E. Kozioł Jacek Banachiewicz Marzena Ucherek Martyna Kandefer-Szerszeń 《Monatshefte für Chemie / Chemical Monthly》2009,140(4):439-444
Abstract (Z)-3-(3,4-diaryl-1,2,4-triazole-5-yl)prop-2-enoic acid derivatives were obtained in the course of the reaction of N
3-substituted amidrazones with maleic anhydride, and isomerized into the (E) isomers by heating under reflux in acetic acid solution. The molecular structure of the compounds obtained was confirmed
by IR and 1H NMR spectroscopy, and by X-ray crystallography for (2E)-3-(4,5-diphenyl-4H-1,2,4-triazol-3-yl)prop-2-enoic acid. The antiviral and immunomodulating activity of several of the compounds was examined.
Graphical abstract
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