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B. A. Puodzhyunaite R. A. Yanchene Z. A. Stumbryavichyute P. P. Mikul'skis 《Chemistry of Heterocyclic Compounds》1986,22(2):206-210
The 1-isopropyl and 1-benzyl derivatives of 1,5-tetrahydrobenzodiazepin-2-one were synthesized by alkylation under the conditions of phase-transfer catalysis. The inversion of the heterocycle was studied by PMR spectroscopy, and the free energies of activation were determined.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 254–258, February, 1986. 相似文献
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B. A. Puodzhyunaite R. A. Yanchene P. B. Terent'ev K. A. Abdurakhmanov G. Dzhumakuliev 《Chemistry of Heterocyclic Compounds》1992,28(7):798-802
Alkylation of 4-methyl-7(8)-nitro-2,3,4,5-tetrahydrobenzodiazepin-2-ones under phase transfer catalytic conditions or in dry acetone occurs only at position 1. The 5-alkyl isomers are obtained by reductive alkylation of 4-methyl-7(8)-nitro-2,3-dihydro-1,5-benzodiazepin-2-ones. The UV, IR, PMR, and mass spectra of the isomeric compounds are reported.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 959–963, July, 1992. 相似文献
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Z. F. Solomko A. N. Kost L. N. Polovina M. A. Salimov 《Chemistry of Heterocyclic Compounds》1971,7(7):922-926
A new synthesis of 1H-2,3,4,5-tetrahydro-1,5-benzodiazepin-2-ones (I) by the reductive cyclization of o-nitro derivatives of N-phenyl--alanine is described. It is more convenient to use the amide of acrylic acid rather than acrylic acid itself, its nitrile, or ester for the synthesis of I from the appropriate o-phenylenediamines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 987–991, July, 1971. 相似文献
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The nitration of 4-methyl-2,3-dihydro-1H-1,5-benzo-2-diazepinone gives the 7 nitro derivative. The 8-nitro isomer was obtained from 4-nitro-1,2-phenylenediamine. The catalytic hydrogenation of the nitrobenzodiazepinones gives the 7- and 8-amino derivatives. The nitrobenzodiazepinones exist in the enol form in alkaline media. 相似文献
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William T. Comer John D. Call W. Lesley Matier Charles M. Combs Stanley J. Dykstra 《Journal of heterocyclic chemistry》1973,10(4):519-525
The preparation of 3-benzenesulfonyl- and 3-benzoyl-2,3,4,5-tetrahydro-3-benzazoein-6(1H)-ones by intramolecular acylation is described. Acid catalyzed rearrangements of these 3-benzazocin-6-ones occurs by 3,4-bond cleavage, which is followed by intramolecular or intermolecular alkylation, to produce indanones (i.e. XIV) or a 3,4-dihydroisoquinoline (II), respectively. In addition to spectral support for these structures, an independent synthesis of II is described from a known 3,4-dihydroisoquinoline. Two rearrangements of 3-benzazocin-6-ones under alkaline conditions are also described, and the products are again evidence for 3,4-bond cleavage to vinylphenones. These beuzazocine rearrangements have been observed only with the 6-keto compounds. 相似文献
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The syntheses of the B-norbenzomorphans, 1,5-methano-2,3,4,5-tetrahydro-1H-2-benzazepine (1a) and its N-methyl derivative (Ib) were accomplished. Phenylsuccinic anhydride (III) was cyclized to 3-carboxy-1-indanone (IVa), which was converted by the Arndt-Eistert method to the homologous methyl indanone-3-acetate (V). One experiment in the synthesis of V led to the by-products 3-carboxamido-1-indanone (IVd) and 3-(N-methylcarboxamido)-1-indanone (IVe), identified by physical and chemical means. Methyl 1-aminoindan-3-acetate (VII) was prepared by catalytic reduction of methyl indanone-3-acetate oxime (VI). Hydrolysis of VII afforded 1-aminoindan-3-acetic acid (VIII), which was cyclized with dicyclohexylcarbodiimide to 1,5-methano-2,3,4,5-tetrahydro-1H-2-benzazepin-3-one (IX). Reduction (lithium aluminum hydride) of IX gave amine Ia which was then methylated to Ib. The mass spectral fragmentation patterns of IX and Ia are discussed. 相似文献
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Synthesis and biological activity of 5-vinyl- and 5-allyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles
Sokolov V. B. Aksinenko A. Yu. Epishina T. A. Goreva T. V. Shevtsova E. F. Dubova L. G. Shevtsov P. N. Rudakova E. V. Kovaleva N. V. Makhaeva G. F. Bachurin S. O. 《Russian Chemical Bulletin》2018,67(11):2103-2107
Russian Chemical Bulletin - A synthetic approach to the vinylation and allylation of tetrahydro-γ-carbolines with alkane dimethyl sulfonates in the presence of sodium hydride was developed.... 相似文献
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O'Donnell CJ Singer RA Brubaker JD McKinley JD 《The Journal of organic chemistry》2004,69(17):5756-5759
A general approach to preparing 1,5-methano- (1) and 1,5-ethano-2,3,4,5-tetrahydro-1H-3-benzazepine (2) is discussed. This strategy involves converting an indanone or tetralone (4) to a cyanohydrin (3) which is subjected to hydrogenolysis followed by lactamization and reduction to provide bicyclic aryl piperidine (1) and bicyclic aryl homopiperidine (2). 相似文献
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Ansari FL Hussain L Nasir S Sultana S 《Rapid communications in mass spectrometry : RCM》2005,19(9):1200-1206
The electron ionization induced fragmentations of ten biologically significant 2,3-dihydro-1,5-benzothiazepines and the corresponding 2,3,4,5-tetrahydro-1,5-benzothiazepines have been studied by low- and high-resolution mass spectrometry. The fragmentations follow a general pattern, the details of which are discussed with respect to the nature and position of the substituent in the aromatic ring. The dihydro- and tetrahydro-1,5-benzothiazepines both undergo fragmentation through four routes (A-D). However, the most significant fragmentation takes place through route A, leading to the elimination of ring A or ring B of the molecule. The difference between the fragmentation patterns of dihydro- and tetrahydro-1,5-benzothiazepines appears mainly in route E where a phenylallylhydroxybenzene cation appears in all tetrahydro-1,5-benzothiazepines but is not observed in the corresponding dihydro derivatives. 相似文献
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DFT B3LYP calculation study was employed to estimate the regioselectivity of an electrophilic aromatic substitution in functionalized 2,3,4,5-tetrahydro-1,5-benzodiazepin-2(1H)-ones. Charge density, frontier molecular orbital study, energetics of σ-complex intermediates of electrophilic substitution reactions in the 2,3,4,5-tetrahydro-1,5-benzodiazepin-2(1H)-ones yield information on different reactivity of aromatic sites. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:263–270, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20015 相似文献
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R. Janciene Z. Stumbreviciute L. Pleckaitiene B. Puodziunaite 《Chemistry of Heterocyclic Compounds》2002,38(6):738-740
When 4-methyl-7-nitro-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one were reacted with phosphorus pentasulfide, the corresponding benzodiazepine-2-thione and its thiol tautomer were formed, which via the 2-methylmercapto derivative were converted to 4-(2-acetylhydrazino)-2-methyl-8-nitro-2,3-dihydro-1H-1,5-benzodiazepine. 相似文献
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[reaction: see text] A new iridium-catalyzed oxidative cyclization of amino alcohols has been revealed. Indole derivatives are synthesized in good to excellent yields from 2-aminophenethyl alcohols by means of a [CpIrCl(2)](2)/K(2)CO(3) catalytic system. The present catalytic system is also effective for syntheses of 1,2,3,4-tetrahydroquinolines from 3-(2-aminophenyl)propanols and 2,3,4,5-tetrahydro-1-benzazepine from 4-(2-aminophenyl)butanol. 相似文献
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B. A. Puodzhyunaite R. A. Yanchene P. B. Terent'ev Z. A. Stumbryavichute G. A. Bulakhov 《Chemistry of Heterocyclic Compounds》1994,30(1):88-93
The conditions were studied o f mono- and diacylation of 7(8)-nitro-2, 3, 4, 5-tetrahydro-1H-1, 5-benzodiazepin-2ones. It was found that under mild conditions (lower temperatures, weak acylating agents), the 7-nitro isomers are acylated only at the 5 -position; increase in the temperature or treatment with an active acylating agent gives the 1,5-diacyl derivatives. Under mild conditions the 8-nitro isomer is not acylated, while under more rigorous conditions a mixture of mono- and diacylated products is formed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 30, No. 1, pp. 99–105, January, 1994. 相似文献
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2-(Bromomethyl)-1-sulfonylaziridines were converted into novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines upon treatment with 2-aminothiophenol in THF in the presence of K2CO3. Starting from 3-substituted 2-(sulfonyloxymethyl)aziridines, a regio- and stereocontrolled synthesis of trans-2-phenyl- and trans-4-(phenyl or propyl)-3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines was developed in good yields via two different reaction pathways, depending on the nature of the sulfonyloxy group. 相似文献
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Agafonov N. E. Dudin A. V. Preobrazhenskii A. A. Zhulin V. M. 《Russian Chemical Bulletin》2001,50(3):560-562
The reactions of aromatic aldehydes with tryptamine (1) in solvents of different polarity were studied. The yields of carbolines in the chosen media decrease with an increase in the donating properties of the aryl substituent, but they markedly increase at a high pressure (5 kbar), especially for compounds with electron-donating aryl groups. The phase transition of dioxane at 5 kbar also sharply increases the yields of the target products. 相似文献