Synthesis of N-Substituted Derivatives of 2-(4-Amino-2-methyl-1H-indol-3-yl)- and 2-(6-Amino-2-methyl-1H-indol-3-yl)acetic Acids

A method was developed for the production of indole compounds containing an amino group at positions 4 and 6 of the benzene ring on the basis of the indolization of the 3-acetylaminophenylhydrazone of ethyl levulinate. A series of derivatives of 2-(4-amino-2-methyl-1H-indol-3-yl)- and 2-(6-amino-2-methyl-1H-indol-3-yl)acetic acids at the 4- and 6-amino group were synthesized.     

2-溴-3-(1H-吲哚-3)-N-甲基马来酰亚胺的合成

以琥珀酰亚胺为起始原料,经过溴化、甲基化后再与吲哚溴化镁加成反应合成了2-溴-3-(1H-吲哚-3)-N-甲基马来酰亚胺,总收率44.8%,其结构经1H NMR和IR确证.     

Synthesis of 6-Methyl-4-(1-methyl-2-buten-1-yl)-2-(2-cyclohexen-1-yl)- and 6-Methyl-4-(1-methyl-2-buten-1-yl)-2-(1-cyclohexen-1-yl)anilines

Alkenylation of 6-methyl-2-(2-cyclohexen-1-yl)- and 2-(1-cyclohexen-1-yl)anilines with piperylene in the presence of AlCl₃ and transformation of the resulting cyclohexenylanilines into carbazole structures were studied.__________Translated from Zhurnal Prikladnoi Khimii, Vol. 78, No. 3, 2005, pp. 441–443.Original Russian Text Copyright © 2005 by Gataullin, Ishberdina, Sotnikov, Abdrakhmanov.     

Rapid and Efficient Synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones and 2,2-Di(1H-indol-3-yl)-2H-acenaphthen-1-ones Catalyzed by p-TSA

An efficient synthesis of 3,3-di(1H-indol-3-yl)indolin-2-ones and 2,2-di(1H-indol-3-yl)-2H-acenaphthen-1-ones via a reaction of various isatins or acenaphthenequinone with indoles in the presence of p-methylbenzene sulfonic acid (p-TSA) in CH₂Cl₂ at room temperature is described. The advantages of this method include good reaction yield, simple workup procedure, and mild reaction condition.     

(S)-2,2,2-三氟-1-(2-甲基-1H-1-吲哚基)乙胺的不对称合成

以2-甲基吲哚为原料,在碱性条件下与α-三氟甲基醛亚胺经加成反应合成了关键中间体——含三氟甲基的(S)-叔丁基亚磺酰胺(3),收率95%,d/r99/1;3脱除保护基得(S)-2,2,2-三氟-1-(2-甲基-1H-1-吲哚基)乙胺(4),收率97%,其结构经1H NMR,13C NMR,19F NMR,FT-IR,EI-MS和HR-EI-MS确证。     

Synthesis and Crystal Structure of N-(2-(1-butyl-3-phenylureido)-1H-indol-3-yl)-N-(4-chlorophenyl)benzamide

<正>The title compound N-(2-(1-butyl-3-phenylureido)-1H-indol-3-yl)-N-(4-chloro- phenyl)- benzamide (C_(32)H_(29)ClN_4O_2, M_r = 537.04) was synthesized by a sequential Ugi four com- ponent condensation (4CC)/aza-Wittig/carbodiimide-mediated cyclization, and the structure was characterized by NMR, IR, MS, elemental analysis and X-ray single-crystal diffraction analysis. The crystal belongs to orthorhombic, space group P2_12_12_1 with a = 11.3663(9), b = 13.3248(10), c = 18.7887(15), V = 2845.6(4)~3, Z = 4, D_c = 1.254 mg/m3, μ = 0.170 mm~(-1), F(000) = 1128, the final R = 0.0538 and wR = 0.1187. X-ray analysis reveals that the new five-membered ring (C(14)-C(15)-N(2)-C(16)-C(21)) and the benzene ring (C(16)-C(21)) are nearly coplanar.     

Efficient synthesis of [6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl]-acetic acid,a novel COX-2 inhibitor

The synthesis of 6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-ylacetic acid (1), a selective cyclooxygenase 2 (COX-2) inhibitor, is described. The synthesis relied on a novel indole formation that involved an alkylation/1,4-addition/elimination/isomerization cascade. It was demonstrated that the entire sequence from sulfonamide 13 and bromoketone 14 to the desired indole (1) could be executed in a single pot.     

Introduction of the 1H-indol-3-yl(phenyl)methyl residue into some CH acids

A new method of introducing the 1H-indol-3-yl(phenyl)methyl residue into some CH acids was developed.     

Ultrasound-assisted synthesis of 3-(1-(2-(1H-indol-3-yl)ethyl)-2-aryl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)indolin-2-ones by novel core-shell bio-based nanocatalyst anchoring sulfonated L-histidine on magnetized silica (SO3H-L-His@SiO2-nano Fe3O4)

An efficient synthesis of 3-(1-(2-(1H-indol-3-yl)ethyl)-2-aryl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)indolin-2-ones is reported via a one-pot three-component reaction of 3-phenacylidenoxindoles, tryptamine, and dimedone under ultrasound irradiation using a newly prepared core-shell nanostructure. The utilized nanocatalyst is obtained by anchoring sulfonated L-histidine amino acid shell, as the bio part, on silica-nanomagnetite core (SO₃H-L-His@SiO₂-nano Fe₃O₄) and characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy (¹H NMR), field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric/differential thermal analysis, vibrating sample magnetometer measurements, transmission electron microscopy, and back-titration. The protocol contains several advantages, such as relatively short reaction times, simple work-up procedure by separation of the catalyst with an external magnet, the use of economical and environmentally friendly ultrasonic waves, and reusability and recoverability of the core-shell nano-promoter for three runs without significant activity loss.     

碘催化的2,2,2-三氟-1-(1H-吲哚-3-基)-乙醇与取代苯胺的傅-克苄基化反应

首次报道了分子碘I₂催化的吲哚衍生物与取代苯胺的傅-克苄基化反应, 合成了8个新型的3-取代吲哚的苯胺类衍生物,收率６５%～９８%,其结构经¹H NMR, ¹³C NMR和HR-ESI-MS表征。     

Synthesis,Characterization, and Antioxidant Properties of Novel 1-(4-Aryl-1,3-thiazol-2-yl)-2-{[1-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methylidene}hydrazines

Russian Journal of Organic Chemistry - A series of novel 1-(4-aryl-1,3-thiazol-2-yl)-2-{[1-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyli­dene}hydrazines were synthesized and properly...     

Synthesis of N-Substituted Derivatives of (5-Amino-2-methyl-1H-indol-3-yl)acetic Acid

A method has been developed for obtaining indole compounds containing an amino group in the benzene ring by the indolization of ethyl levulinate p-acetaminophenylhydrazone. A series of derivatives of (5-amino-2-methyl-1H-indol-3-yl)acetic acid at the 5-amino group has been synthesized.     

Facile Synthesis of Unsymmetrical N-Aryl-2, 2-di(1H-indol-3-yl) Acetamide Derivatives

A facile and highly efficient method has been developed for the synthesis of unsymmetrical N-aryl-2,2-di(1H-indol-3-yl)acetamide derivatives by regioselective Friedel-Crafts alkylation of the N-aryl-2-hydroxy-2-(1H-indol-3-yl) acetamide derivatives with various indoles catalyzed by 2 mol/L H₂SO₄ at room temperature in a short reaction time, the yield was up to 94%.     

Novel N-Alkyl-4-(6-fluoro-1H-indol-3-yl)benzamide Derivatives as Anticancer Agents: Design,Synthesis, Biological Evaluation,and Molecular Docking Study

Russian Journal of Organic Chemistry - A number of novel N-alkyl-4-(6-fluoro-1H-indol-3-yl)benzamide derivatives were synthesized and characterized with modern spectroscopic techniques (NMR, IR,...     

1-(2-氨基-3,5-二氰基-4-芳基-4H-吡喃-6-基)愈创兰烃薁的合成

在醋酸铵作用下,通过1-氰乙酰基愈创兰烃薁、芳香醛、丙二腈的三组分反应,一锅法合成了一系列1-(2-氨基-3,5-二氰基-4-芳基-4H-吡喃-6-基)愈创兰烃薁衍生物.该反应操作简单、条件温和、收率良好.产物结构经NMR,MS,IR及元素分析等得以证实.