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1.
(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. Reactions of (chromon-3-yl)bis(indol-3-yl)methanes with guanidine carbonate and hydrazine hydrate proceed with the participation of the chromone ring system and lead to the formation of the corresponding pyrimidines and pyrazoles bearing the bis(indol-3-yl)methyl moiety. 相似文献
2.
Series of 3-arylalkyl- or 3-alkylamino-4-(indol-1-yl)maleimides and bis(indol-1-yl)maleimides were synthesised. The cyclization of the 3-substituted 4-(indol-1-yl)maleimides under the action of acids resulted in the formation of diazepine[1,4] derivatives with indoline and maleimide nuclei annelated. These compounds readily produced the corresponding indolomaleimidodiazepines[1,4] after dehydrogenation. 相似文献
3.
Eu(NTf2)3催化吲哚与醛(酮)反应合成二吲哚基甲烷 总被引:3,自引:0,他引:3
二(三氟甲基磺酰)亚胺铕(Ⅲ)[Eu(NTf2)3,Tf=SO2CF3]作催化剂,吲哚与醛(酮)在室温下发生亲电取代反应合成了一系列二吲哚基甲烷,产率85%~98%.该法反应条件温和、时间短、催化剂用量少且可以回收重复使用. 相似文献
4.
(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
5.
B3LYP/6-31G(d) density functional quantum chemical calculations of vicinally substituted bis(indol-1-yl)derivatives of 1,5-dihydropyrrol-2-one,
furan-2,5-dione, cyclopent-4-ene-1,3-dione, cyclobut-3-ene-1,2-dione, and pyrrolidine-2,5-dione were carried out to study
the effect of modification of the maleimide moiety in 3,4-bis(indol-1-yl)maleimides on the direction of intramolecular cyclization
under the action of protic acids. Geometric parameters, charge distributions, energy characteristics, and frontier orbital
energies of these compounds and the corresponding indoleninium cations were determined. Alternative protonation routes of
3,4-bis(indol-1-yl)-1,5-dihydropyrrol-2-one have been studied.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1348–1352, July, 2008. 相似文献
6.
A method has been developed to sequentially add indole-3-mercurials to dichlorinated quinones using palladium catalysis. These reactions can be used in the modular assembly of bis(indol-3-yl)benzoquinones, a significant natural product family. 相似文献
7.
Md. Shahajahan KutubiTsugio Kitamura 《Tetrahedron》2011,67(42):8140-8145
Intermolecular hydroarylation of propynoic acid and its esters with indoles proceeded efficiently in acetic acid under a catalytic system of FeCl3/3AgOTf and afforded the corresponding 3,3-bis(indol-3yl)propanoic acids and their esters in high yields. In the case of 2-methylindole, 3-indolylacrylic acid and its ethyl ester were obtained in high yields. This iron-catalyzed hydroarylation showed a high regioselectivity at the 3-position of indoles and a high utility for the synthesis of bis(indol-3-yl) compounds, which are important for biological and pharmaceutical fields. 相似文献
8.
二(三氟甲基磺酰)亚胺铕(III) [Eu(NTf2)3, Tf=SO2CF3]作催化剂, 吲哚与醛(酮)在室温下发生亲电取代反应合成了一系列二吲哚基甲烷, 产率85%~98%. 该法反应条件温和、时间短、催化剂用量少且可以回收重复使用. 相似文献
9.
Lysenkova L. N. Reznikova M. I. Korolev A. M. Preobrazhenskaya M. N. 《Russian Chemical Bulletin》2001,50(7):1309-1313
Transformation of ascorbigen in an acidic medium, which affects the carbohydrate moiety of the molecule and results in the formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone, 5-hydroxymethyl-2-(indol-3-yl)methylidenetetrahydrofuran-3-one, and 2-(indol-3-yl)acetylfuran, was investigated. Isolation and identification of the intermediates allowed the elucidation of the mechanism of this domino-type reaction. 相似文献
10.
V. M. Berestovitskaya I. A. Litvinov E. A. Ishmaeva L. I. Deiko Ya. A. Vereshchagina Z. M. Sarkisyan A. G. Gubaidullin G. R. Fattakhova S. V. Makarenko G. A. Berkova 《Russian Journal of General Chemistry》2004,74(1):110-119
A method was developed for preparing first representatives of phosphorylated nitrovinylindoles, bis(2-chloroethyl) 1-(indol-3-yl)- and bis(2-chloroethyl) 1-(1-alkylindol-3-yl)-2-nitroethenylphosphonates, and the structures of these compounds were studied. The spectroscopic data and results of dipole moment measurements show that the molecules have E configuration with s-cis arrangement of the multiple bond and phosphoryl group. X-ray studies have shown that the molecules of the first compound, having the E-s-cis form in the solid phase also, exist in the crystal in the form of enantiomeric pairs. They are involved in inter- molecular hydrogen bonds to form infinite chains. 相似文献
11.
Panov Alexey A. Lakatosh Sergey A. Kubbutat Michael H. G. Dezhenkova Lyubov G. Totzke Frank Schechtel Kristof 《Chemistry of Heterocyclic Compounds》2019,55(11):1050-1059
Chemistry of Heterocyclic Compounds - Several previously unknown derivatives of 3,4-bis(indol-1-yl)maleimide, as well as 3-(2,3-dihydroindol-1-yl)-4-(indol-1-yl)maleimide were synthesized as... 相似文献
12.
A. M. Korolev L. N. Yudina E. I. Lazhko M. I. Reznikova M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》1999,35(5):561-569
Under the influence of acids 3-formylindole forms urorosein (the salt of di(indol-3-yl)methylium) which is unstable in solution
and decomposes to give a series of indole derivatives, among which 6-(indol-3-yl)-5H,7H-indolo[2,3-b]carbazole and tri(indol-3-yl)methylium
salt predominate. N,N′-Dimethylurorosein in solution also forms a mixture of indole derivatives, from which tri(1-methylindol-3-yl)methylium
salt, 5N,11N-dimethylindolo[3,2-b]carbazole and its 6-(1-methylindol-3-yl) derivative were isolated.
Research Institute of New Antibiotics, RAMN (Russian Academy of Medical Science), Moscow 119867, Russia; Translated from Khimiya
Geterotsiklicheskikh Soedinenii, No. 5, pp. 631–639, May, 1999. 相似文献
13.
The reaction of 2-phenyl- and 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2-CH3COOH) in benzene leads mainly to the formation of the isonitroso and 3-nitroso indole derivatives, respectively. When reacted with nitrous acid, 1-methyl-2-phenylindole gives also the corresponding azo-bis-indole in good yields. The reaction of indole with nitrogen dioxide leads to 2-(indol-3-yl)-3H-indol-3-one as the main product together with small amounts of 2-(indol-3-yl)-3H-indol-3-oxime; whereas the major product obtained when the same indole is reacted with nitrous acid is represented by 2-(indol-3-yl)-3H-indol-3-oxime. The reaction of 3-alkyl substituted indoles with nitrogen dioxide is rather complex and results in the formation of different nitro indoles, whereas nitrosation is observed when nitrous acid is used. Crystal structures of 2-(indol-3-yl)-3H-indol-3-one and of 4-nitro-N-acetyltryptamine have been determined by X-ray analysis. 相似文献
14.
Indol-3-yl 1-methyl-1,2,5,6-tetrahydropyridin-4-yl ketone (1d) can be isomerised to indol-3-yl l-methyl-l,2,3,4-tetrahydropyridin-4-yl- ketone but the protonated form of this enamine could not be cyclised to the indole α-position. Both indol-2-yl l-methyl-l,2,5,6-tetrahydropyridin-4-yl ketone (1c) and its isomer (1d) were cyclised to 5-membered ketones by mineral acid catalysed Michael-type addition of indole β- and α-positions respectively onto the unsaturated ketone systems. Ketone (1d)was transformed to l-acetylindol-3-yl 3-acetyl-l,4,5,6-tetrahydropyridin-4-yl ketone by hot acetic anhydride. Strong base treatment of indol-3-yl(l,2,5,6-tetrahydropyridin-4-yl) methane caused isomerisation of the double bond into conjugation with the indole rather than into the endocyclic enamine position. 相似文献
15.
A. V. Sadovoy A. E. Kovrov G. A. Golubeva L. A. Sviridova 《Chemistry of Heterocyclic Compounds》2011,46(10):1215-1223
The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads
exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones. 相似文献
16.
A series of nicotyl-fused indolo-pyrazoles (NFIPs) were synthesized by a one-pot multicomponent reaction of aryl aldehydes, isoniazid, and indole in the presence of zeolite as a catalyst. Structures of all the synthesized compounds were established by IR, 1H-NMR, 13C-NMR, 2D-NMR, TOF-MS, and elemental analysis. The products were obtained in excellent yields and high purity. All 10 compounds were screened for larvicidal and insecticidal properties against Anopheles arabiensis and tested for their lipoxygenase inhibitory activity. Compounds (3-(3-hydroxy-4-methoxyphenyl)-2,3-dihydropyrazolo[4,3-b]indol-1(4H)-yl)(pyridin-4-yl)methanone ( 4i ) and (3-(3-bromo-5-hydroxy-4-methoxyphenyl)-2,3-dihydropyrazolo[4,3-b]indol-1(4H)-yl)(pyridin-4-yl)methanone ( 4j) displayed highest larvae mortality at a 4 μg/ml dose in 24 h. Compounds (3-(4-methoxyphenyl)-2,3-dihydropyrazolo[4,3-b]indol-1(4H)-yl)(pyridin-4-yl)methanone ( 4h ) and (3-(3-hydroxy-4-methoxyphenyl)-2,3-dihydropyrazolo[4,3-b]indol-1(4H)-yl)(pyridin-4-yl)methanone ( 4i ) showed a significant knockdown activity after 24 h with 70% mortality. Furthermore, (3-(4-chlorophenyl)-2,3-dihydropyrazolo[4,3-b]indol-1(4H)-yl)(pyridin-4-yl)methanone ( 4c ) and (3-(3-bromo-5-hydroxy-4-methoxyphenyl)-2,3-dihydropyrazolo[4,3-b]indol-1(4H)-yl)(pyridin-4-yl)methanone ( 4j ) displayed promising lipoxygenase inhibitory activity with a mortality of 70% and 60%, respectively. 相似文献
17.
蒙脱土K10-ZnCl2催化下研磨法合成二吲哚甲烷衍生物 总被引:5,自引:0,他引:5
蒙脱土K10固载ZnCl2是一个有效的环境友好催化剂. 在蒙脱土K10-ZnCl2催化下, 将吲哚与芳香醛混合在研钵中研磨2~8 min, 可得到收率为66%~97%的二吲哚甲烷衍生物. 该方法具有操作简便、反应条件温和、反应时间缩短、 对环境友好等优点. 相似文献
18.
Makoto Nishiki Wataru Oi Kazuaki Ito 《Journal of inclusion phenomena and macrocyclic chemistry》2008,61(1-2):61-69
The anion binding properties of the indolylmethanes (1) were investigated by 1H-NMR spectroscopy in CDCl3. Tris(3-methylindol-2-yl)methane (1a) selectively bound a chloride anion the over other tested anions (Br?, I?, HSO 4 ? , and NO 3 ? ). In contrast, analogous compounds, phenyl bis(3-methylindol-2-yl)methane (1b), 2-hydroxyphenyl bis(3-methylindol-2-yl)methane (1c), tri(indol-3-yl)methane (1d), and phenyl di(indol-2-yl)methane (1e), showed a low anion binding ability and selectivity. These results indicate that the number and a position of the binding sites (indole NH protons) of the indolylmethanes are important factors for the formation of the complex with an anion. The high binding ability and selectivity of 1a toward a chloride anion is attributed to the proper size of the binding pocket for a chloride anion and the formation of multiple hydrogen bonds between the three indole NH protons and a chloride anion. The anion affinity of 1a was significantly affected by the cation component of quaternary ammonium salts, indicating that it is ion pair binding and not solely anion binding. 相似文献
19.
Hung M. Nguyen Nikita E. Golantsov Alexandra S. Golubenkova Victor B. Rybakov Leonid G. Voskressensky 《Molecules (Basel, Switzerland)》2021,26(9)
A multicomponent reaction of isocyanides with aryl(indol-3-yl)methylium salts and amines has been found. A series of aryl(indol-3-yl)acetimidamides was obtained in up to 96% yields. In the case of ethyl isocyanoacetate, the reaction is followed by cyclization to form 3,5-dihydro-4H-imidazol-4-one derivatives. 相似文献
20.
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