3-丁烯酮-吲哚衍生物的合成

吲哚类化合物广泛存在于植物界中, 且具有多种生理活性。其中, 月橘烯碱具有抗生育活性。本文以合成月橘烯碱的中间体3-(1-丁烯酮-3)吲哚为起始物, 并设计了10个与其结构类似的单吲哚化合物, 并做了小鼠的药理实验。     

Synthesis of hexahydrocarbazoles by cyclisation of 3-(but-3-enyl) indole derivatives

A new cyclisation of 3-(but-3-enyl) indole derivatives that produces policyclic compounds with a hexahydrocarbazole structure is described. In this reaction three stereogenic centres are generated in one step, and this process can be considered as evidence of the biogenetic relationship between anominine and tubingensin A.     

Synthesis of alkyl indole derivatives

Condensation of arylamines with α-halogenoketone afforded the intermediate anilino-ketones which on direct cyclization furnished the corresponding alkylindoles. Synthesis of 2,3,5-trimethyl-4,7-dimethoxyindole (5a) and 2,3,6-trimethyl-7-methoxyindole (5b) is described. Earlier (1) synthesis of 2,3-dimethyl-4,7-dimethoxyindole and 1,2,3-trimethyl-4,7-dimethoxy-indole is reported.     

Indole derivatives. 120. Synthesis of higher ω-(3-indolyl)alkanoic acids by alkylation of indole lactones

The alkylation of indole with the tridecanolide, pentadecanolide, and oxo lactones of ω-hydroxyethoxyundecanoic and ω-hydroxybutoxyundecanoic acids was investigated. Higher indolylalkanoic acids, viz., ω-(3-indolyl)undecanoic, ω-(3-indolyl)tride-canoic, and ω-(3-indolyl)pentadecanoic acids, were obtained. The scheme of the alkylation of indole with oxo lactones, and the difference in the rates of the reactions of the ester and lactone bonds, were established from the reaction products. See [1] for communication 119. Translated from Khimiya Getetotsiklicheskikh Soedinenii, No. 2, pp. 216–217, February, 1980.     

Synthesis of 5-(p-chlorophenylsulfonyl)indole and some of its derivatives

The synthesis of the previously unknown 5-(p-chlorophenylsulfonyl)indole with a free -position is described. Derivatives of the new compound containing functional substituents at the 2-position of the indole ring were prepared.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 54–56, January, 1991.     

Synthesis of indole derivatives via isocyanides

Fast and convenient approaches to the indole nucleus from isocyanides are reviewed as a means for the tailored preparation of conveniently functionalized indoles by using the unique reactivity of isocyanides in one-pot multicomponent and cascade reactions.     

Indole derivatives 138. Synthesis of some new sulfur-containing derivatives of indole

2-Ethoxycarbonyl-5-(p-nitrophenylthio)indole and the corresponding acid were obtained by the E. Fischer reaction. Decarboxylation of the acid gave 5-(p-nitrophenylthio)indole. The geometric isomers of the initial hydrazone of ethyl pyruvate were isolated and characterized.For Communication 137, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1508–1511, November, 1991.     

Synthesis of some N-substituted derivatives of diethyl phosphoramidate

Summary Some N-substituted derivatives of diethyl phosphoramidate are described. They were prepared by the action of various halogen compounds on the N-sodium derivative of diethyl N-methylphosphoramidate.     

Synthesis and properties of derivatives ofsym-triazine. 15. Synthesis of amine derivatives ofsym-triazine that contain indole groups

By the cyclocondensation of imino esters of acids of the indole series with N-acylguanidines, 2-amino-4,6-disubstituted sym-triazine are obtained that contain indole groups. The reaction of N-(indolyl-3-imidolyl)-guanidine with esters of carboxylic acids leads to 2-amino-4-(3-indolyl)-6-substituted sym-triazines. Indolyl-containing N-subsitituted 2,4-diamino-sym-trizines are synthesized by the reaction of imino esters of indole acids with biguanides. Similar products are also formed when 2-amino-4-trichloromethyl-sym-triazines that contain indole substituents react with dimethylamine, morpholine, or furfurylamine.I. M. Gubkin State Petroleum and Gas Academy, Moscow, 117917. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 214–223, February, 1995. Original article submitted December 21, 1994.     

Capillary gas chromatography of metal chelates of diethyl dithiocarbamates

Summary Capillary GC of metal chelates of diethyl dithiocarbamate (DDTC) was examined on a methylsilicone DB-1 column, (25 meter, 0.2 mm. i.d) with a film thickness of 0.25 μm. Elution was carried out at the initial column temperature of 180°C and programmed at 5°C min⁻¹ to 260°C. Detection was by FID or ECD. Symmetrical peaks with base line separation were obtained with the metal chelates of copper(II), nickel(II), cobalt(III), manganese(II) and chromium(III). The ECD gave better sensitivity than the FID with a linear calibration range of 5–50 μg mL⁻¹ and detection limits 2.0–6.0 μg mL⁻¹, corresponding to 111–333 pg of metal ion reaching the detector. The method was applied to the determination of metal ions in water and pharmaceutical preparations with a coefficient of variation (CV) within 4.0%. When compared with a standard flame AAS method the results revealed no significant difference.     

Synthesis of N-alkyl derivatives of 4-(2′-aminoethyl)indole

N-Substituted 4-(2′-aminoethyl)indoles are attainable in good yields from indole-4-acetic acid ( 2 ). Several methods of preparation for 2 were tried or considered. A new sequence involving Arndt-Eistert homologation of indole-4-carboxylic acid has been devised, which is no more laborious than a literature homologation sequence involving indole-4-acetonitrile, and which provides somewhat better overall yields than the literature method.     

Synthesis of 3-alkenylated indole and bis(indol-3-yl) derivatives catalyzed by sulfonic acid-functionalized ionic liquid under ultrasound irradiation

A simple and efficient protocol has been developed for the synthesis of 3-alkenylated indoles and bis(indol-3-yl) derivatives by sulfonic acid-functionalized ionic liquid-catalyzed reaction of indole with 1,3-diketones/3-ketoesters under solvent-free ultrasound irradiation. Good to excellent yields (68–94%) are obtained in ultrasonication. The product of reaction is dependent on the substituent at C-2 position of indole. The catalyst is reusable and recyclable up to four cycles without significant loss of its catalytic activity. Compared with conventional heating, sound wave activation has the considerable advantages such as shorter reaction time, easy work-up, higher yields, and mild conditions.     

New derivatives of 3-aminoindole. Synthesis of 2-aryl(hetaryl)-3-(3,5-dimethyl-1-pyrazolyl)indoles

The interaction of arylhydrazines with ù-(3,5-dimethyl-1-pyrazolyl)acetophenones and acetyl(2-thiophene) leads to arylhydrazones, which are converted by Fischer cyclization into 2-aryl(thienyl)-3-(3,3-dimethyl-1-pyrazolyl)indoles with substituents in positions 1, 5, and 7.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1662–1669, November, 2004.     

Conversion of ascorbigen and its derivatives to substituted 1-deoxy-1-(indolyl-3)-α-L-sorbopyranose

A new reaction involving L-ascorbic acid have been found. Under the action of alkali, ascorbigen and its N-alkyl derivatives undergo cleavage of the lactone ring, decarboxylation, and rearrangement to give 1-deoxy-1-(inolyl-3)--L-sorbopyranose and its N-alkyl derivatives. The structures of the compounds obtained were confirmed by mass-spectroscopy and PMR spectroscopy.Translated from Khimiko Geterotsiklicheskikh Soedinenii, No. 5, pp. 607–610, May, 1989.     

New pyrylium derivatives in the indole series

Nitrogen-unsubstituted 2,3-dihydroindole and its homologs, as well as 1,2,3,4-tetrahydro-- carbolines, react with 2,6-dimethyl-4-methoxypyrylium perchlorates to give N-pyrylated derivatives of indole, which are converted to the corresponding pyridine bases by the action of ammonium salts and form 1-aminopyridinium derivatives with hydrazine hydrate.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1531–1533, November, 1972.     

Bis(indolyl-3-)phthalides and their spectral properties

Symmetrical bis-indolylphthalides, having electron-releasing and electron-withdrawing substituents on the indole rings, were obtained from the reaction between an indole and an unsubstituted or substituted phthalic anhydride. Unsymmetrical indolylphthalides were synthesized by the condensation of 3-(o-carboxybenzoyl)indole with a substituted indole. A relationship was found to exist between the nature of the substituent, and the spectral and acid-base properties of the compounds.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 915–918, July, 1989.