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1.
2,3-Disubstituted indoles were synthesized by solid-phase reaction using the Fischer indole synthesis. A "traceless" silicon linker was employed with the silicon-carbon bonding being cleaved with TFA. An oxygen atom was placed into the middle of the spacer/linker so as to enhance solid-phase synthesis by better solvation. 相似文献
2.
Studies on the Fischer indole synthesis 总被引:1,自引:0,他引:1
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Nitrogen-substituted methyl -phenyl--hydrazinocrotonates form methyl 3-phenyl-2-indolylacetates or methyl 2-benzylindole-3-carboxylates in acid media. The latter react with polyphosphoric acid to give benzo[b]carbazole derivatives, from which the corresponding 6,11-dioxobenzo[b]carbazoles are obtained by oxidation.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1079–1082, August, 1972. 相似文献
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The parallel solid phase synthesis of an 18-member library of 2-substituted pyrimidines is described using a chlorogermane-functionalised resin. The success of the key Pinner-type condensations between a resin-bound enaminone and an array of amidine hydrochlorides highlights the stability of arylgermane linkers (cf. arylsilanes) towards strongly basic/nucleophilic conditions. 相似文献
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Sun CM Swamy KM Lin MJ Yeh WB Chen FY Tseng WH 《Combinatorial chemistry & high throughput screening》2003,6(2):133-137
Liquid phase combinatorial synthesis (LPCS) of piperazinediones by the use of soluble polymer support is explored to generate libraries. Proline anchored polyethylene glycol monomethyl ether (PEG) underwent dipeptide formation with different Fmoc-amino acids in the presence of dicyclohexyl carbodiimide (DCC). Deprotection of Fmoc accompanied with the cleavage from polymer support with cyclization of dipeptide to piperazinediones offers a facile and effective way to prepare diverse combinatorial libraries. Excellent yields and purities were achieved by simple wash and precipitation method. 相似文献
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Functionalized indoles are synthezised under mild conditions in a tartaric acid-dimethylurea melt. The melt serves as the solvent and as the catalyst. Under these reaction conditions, sensitive functional groups such as N-Boc, N-Cbz, or azides are stable, and indolenines are obtained regioselectively in excellent yields. The practical use of the method is demonstrated in the synthesis of the hormone melatonin. 相似文献
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[reaction: see text] Bartoli indole synthesis has been performed for the first time on solid supports. Starting from Merrifield resin, immobilization of five nitro benzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic cleavage leads to substituted methyl indole carboxylates in excellent purities. Features of this reaction are the stability of halide groups, ester moieties, and tolerance of o,o'-unsubstituted nitro resins. Heck and Sonogashira reactions are also possible with immobilized indoles. 相似文献
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T. Dhanabal 《Tetrahedron letters》2005,46(26):4509-4510
A new synthesis of an indoloquinoline alkaloid, isolated from Cryptolepis sanguinolenta, is described using a Fischer indole cyclization. 4-Hydroxy-1-methyl-1H-quinolin-2-one reacted directly with phenylhydrazine hydrochloride to give the indoloquinoline, which was reacted with POCl3 and then the resultant halide hydrogenolysed to give cryptosanguinolentine. 相似文献
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A p-TsOH promoted one-pot synthesis of multi-substituted 2-trifluoromethyl indole derivatives, for instance, 2-trifluoromethyl-3-phenylindoles, 2-trifluoromethyl-indole-3-propanoates, and 2-trifluoromethyl-indole-3-butanoates from reactions of 1,1,1-trifluoro-3-phenylacetone and simply prepared ω-trifluoromethyl substituted δ and ?-ketoesters with arylhydrazines via Fischer indole synthesis has been developed. 相似文献
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N. M. Przheval'skii L. Yu. Kostromina I. I. Grandberg 《Chemistry of Heterocyclic Compounds》1988,24(7):709-721
Recent data on the mechanism of the rearrangement of arylhydrazones to indoles (the Fischer reaction) are examined. The effect of electronic factors and the acidity of the medium on the rate of the process is discussed. The regioselectivity of the indolization reaction and its quantum-chemical interpretation are analyzed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 867–880, July, 1988. 相似文献
12.
William C. Neuhaus Ian J. Bakanas Joseph R. Lizza Charles T. Boon Jr. 《Green Chemistry Letters and Reviews》2016,9(1):39-43
Novel eco-friendly tetramethylguanidinium propanesulfonic acid trifluoromethylacetate ([TMGHPS][TFA]) ionic liquid was developed as catalyst and medium for the Fischer indole synthesis of a wide variety of hydrazines and ketones. The indole products were isolated in high yields and with minimal amounts of organic solvent. This reaction showed that [TMGHPS][TFA] can be regenerated and reused with reproducible yields without eroding the integrity of the ionic liquid. 相似文献
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Philip E. AlfordLiangfeng Fu Joseph K. KubertLingshan Wang Gordon W. Gribble 《Tetrahedron letters》2011,52(21):2642-2644
Both symmetrical and unsymmetrical 2,3′-biindoles are efficiently synthesized in good to excellent yields by Fischer indole synthesis. The scope of the method was evaluated by examining substituent effects with para-substituted hydrazines and 3-acylindoles. 相似文献
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Organic transformations on substrates which are immobilized on an insoluble, polymeric carrier have found broad application in compound collection synthesis. In contrast to other synthetic methodologies in solid-phase organic synthesis, reactions that afford non-racemic products are strikingly under-represented. Not only does the introduction of stereoinformation on immobilized, achiral starting materials provide enantioenriched products which can be of value for biological testing, but it also opens up new perspectives for accessible structures. This feature article gives an overview of successful enantioselective transformations on a solid support. Critical differences in the corresponding solution-phase protocols are highlighted, and applications to the generation of compound collections are particularly mentioned. 相似文献
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Zahra Ghiyasabadi Saeed Bahadorikhalili Mina Saeedi Mona Karimi-Niyazagheh Seyedeh Sara Mirfazli 《Journal of heterocyclic chemistry》2020,57(2):606-610
In this work, an efficient, user-friendly, and simple procedure was reported for the preparation of indole derivatives catalyzed by the heterogeneous SBA-15-Pr-SO3H via Fischer indole pathway. The title compounds were synthesized from various arylhydrazines and ketones in the presence of 3 mol% of the catalyst in the refluxing ethanol. 相似文献
16.
[reaction: see text] We describe a new approach for the solid-phase synthesis of indoles 1 that involves a one-pot release and cyclization reaction of a solid-supported hydrazone through a Wang-type linker. Using this solid-phase methodology, we accomplished the synthesis of 40 naltrindole derivatives. 相似文献
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In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange, quenching with di-tert-butyl azodicarboxylate, followed by reaction with ketones under acidic conditions. 相似文献
18.
Christopher A. Simoneau 《Tetrahedron》2005,61(48):11374-11379
New 3-component variations of the Fischer synthesis of substituted indoles have been developed based on the reaction of organometallic reagents with nitriles or carboxylic acids. The new variations expand the scope and synthetic utility of the method. 相似文献
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Two-step route to indoles and analogues from haloarenes: a variation on the Fischer indole synthesis
In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines. 相似文献