- Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst
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Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.
- Misal Castro, Luis C.,Sultan, Ibrahim,Nishi, Kohei,Tsurugi, Hayato,Mashima, Kazushi
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p. 3287 - 3299
(2021/03/01)
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- Tetrahydrocarbazoles by mechanochemical Fischer indolisation
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The Fischer indolisation (FI) typically proceeds in the presence of a Br?nsted or Lewis acid in an organic solvent at elevated temperatures. Herein, we report that tetrahydrocarbazoles (THCs) are accessible by mechanochemical FI at ambient temperature. Using phenylhydrazine hydrochlorides in the presence of silica is critical for this solid-state variant of the FI.
- Qiu, Yichen,Puni, Kararaina Te,Duplan, Clotilde C.,Lindsay, Ashley C.,Sperry, Jonathan
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supporting information
(2021/05/26)
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- SBA-15-Pr-SO3H catalyzed one-pot synthesis of indole derivatives via Fischer indole pathway
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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.
- Ghiyasabadi, Zahra,Bahadorikhalili, Saeed,Saeedi, Mina,Karimi-Niyazagheh, Mona,Mirfazli, Seyedeh Sara
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supporting information
p. 606 - 610
(2020/01/03)
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- Annulation of Indoles with 1,n-Dibromoalkanes by a Pd(II)-Catalyzed and Norbornene-Mediated Reaction Cascade
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Employing 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane as biselectrophiles, the annulation of indoles was probed in the presence of PdCl 2 (MeCN) 2 as a catalyst and norbornene as a transpositional ligand. Ring formation to a five-membered ring was observed at positions C2 and N, while annulation of a six-membered ring occurred at positions C2 and C3. The latter cascade process was successfully applied to the direct synthesis of 1,2,3,4-tetrahydrocarbazoles from indoles (11 examples, 31-68% yield). Seven-membered-ring annulation was feasible by an initial coupling at positon C2 followed by alkylation at C3.
- Bach, Thorsten,Henkel, Michael
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p. 1231 - 1238
(2020/04/15)
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- Design, synthesis, in vivo and in vitro studies of 1,2,3,4-tetrahydro-9H-carbazole derivatives, highly selective and potent butyrylcholinesterase inhibitors
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Abstract: Inhibition of butyrylcholinesterase (BChE) might be a useful therapeutic target for Alzheimer’s disease (AD). A new series of 1,2,3,4-tetrahydro-9H-carbazole derivatives were designed synthesized and evaluated as BChE inhibitors. While all of the derivatives have shown for AChE IC50 values below the detectable limit (> 100?μM), they were selective potent BChE inhibitors. 1-(2-(6-fluoro-1,2,3,4-tetrahydro-9H-carbazole-9-yl)ethyl)piperidin-1-ium chloride (15?g) had the most potent anti-BChE activity (IC50 value = 0.11?μM), the highest BChE selectivity and mixed-type inhibition. Pharmacokinetic properties were accordant to Lipinski rule and compound 15g demonstrated neuroprotective and inhibition of β-secretase (BACE1) activities. Furthermore, in vivo study of compound 15g in Morris water maze task has confirmed memory improvement in scopolamine-induced impairment. All results suggest that new sets of potent selective inhibitors of BChE have a therapeutic potential for the treatment of AD. Graphical abstract: A new series of 1,2,3,4-tetrahydro-9H-carbazole derivatives were designed synthesized and evaluated as BChE inhibitors. While all of the derivatives have shown for AChE IC50 values below the detectable limit, they were selective potent BChE inhibitors. Compound 15g had the most potent anti-BChE activity. All results suggest that new sets of potent selective inhibitors of BChE have a therapeutic potential for the treatment of AD.[Figure not available: see fulltext.]
- Ghobadian, Roshanak,Esfandyari, Roghaieh,Nadri, Hamid,Moradi, Alireza,Mahdavi, Mohammad,Akbarzadeh, Tahmineh,Khaleghzadeh-Ahangar, Hossein,Edraki, Najmeh,Sharifzadeh, Mohammad,Amini, Mohsen
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p. 211 - 223
(2019/04/17)
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- Synthesis and evaluation of indole derivatives as photosynthesis and plant growth inhibitors
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Indole derivatives were synthetized based on the Fischer indole methodology using different phenyl hydrazine hydrochlorides and either cyclohexanone or 2-butanone. The pre- and post-emergent herbicidal activities were evaluated against Ipomoea grandifolia. A carbazole, 6-chloro-2,3,4,9-tetrahydro-1H-carbazole (3b), decreased the PIabs parameter by 32% and increased the cross-section related parameters, indicating the inactivation of the reaction center on photosystem II. Compound 3b acts as a post-emergent herbicide prototype since dry biomass was reduced by 50%, corroborating the fluorescence results. Comparing instead with a germination experiment, 2,3,4,9-tetrahydro-1H-carbazole (3a) was found to be the most effective agent, inhibiting seed germination by 22% and decreasing root length by 50%. The tetrahydrocarbazoles showed better results than indole derivatives potentially due to the presence of methylene groups at structures, which increase the compounds' lipophilicity and may facilitate their access to the plant. In addition, electron withdrawing groups on the aromatic ring were found to correlate with increased herbicide activity. Further optimization of this series towards the development of herbicides is ongoing.
- Mendes, Mylla Cristie Da Silva,Fazolo, Bruno Rodrigues,De Souza, Jéssica Maria,De Vasconcelos, Leonardo Gomes,De Sousa Junior, Paulo Teixeira,Dall'Oglio, Evandro Luiz,Soares, Marcos Ant?nio,Sampaio, Olívia Moreira,Vieira, Lucas Campos Curcino
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p. 1350 - 1358
(2019/06/19)
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- Catalytic Oxidative Coupling Cyclization for Construction of Benzofuroindolenines under Mild Reaction Conditions
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We describe iron-catalyzed oxidative coupling cyclization of tetrahydrocarbazoles or THβCs or THγCs to form benzofuroindolenines as fused polycyclic indoles. This mild, efficient and simple approach afforded a library of more than 52 complex compounds across a range of substrate classes with good to excellent yields. (Figure presented.).
- Lin, Yuqi,Ye, Jinxiang,Zhang, Wenting,Gao, Yu,Chen, Haijun
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supporting information
p. 432 - 435
(2018/12/13)
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- Design, synthesis and pharmacological evaluation of some novel tetrahydrocarbazoles as potential COX-2 inhibitors
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Background: NSAIDs have been extensively used for the treatment of pain and inflammation. There are about 30 different NSAIDs available in market and about 80 percent of prescriptions throughout the world contains one or the other painkiller. Chronic use of these drugs has many side effects such as gastric ulceration and the COX-2 inhibitors suffer from major drawback of cardiac toxicity. The need for a potential and safe NSAIDs has always led to the development of newer, better and safer drug molecules. In this article design and development of tetrahydrocarbazole derivatives with very low ulcerative index is reported. Methods: Fifteen tetrahydrocarbazole derivatives were synthesized on the basis of structural homology to indomethacin. Compounds were synthesized and characterized on the basis of spectral data. These were studied for their analgesic, anti-inflammatory and ulcerogenic activities. These compounds were subjected to molecular docking studies for understanding the possible mechanism of action and target. Results: The designed compounds were synthesized successfully in good yield and purity without much efforts. All compounds were evaluated by in vitro and in vivo assay, molecular modelling studies and ulcerative index. One of the compound (3-Aminophenyl) (6-chloro-1,2,3,4-tetrahydro-9H-carbazol-9-yl) methanone 13 was found to be highly active in the in vitro and in vivo assessment also it was found to be highly safe on ulcerogenic index compared to the standard drugs. Conclusion: Tetrahydrocarbazoles were found to be promising scaffolds which can be developed into safe and potential non-steroidal anti-inflammatory agents.
- Sakinala, Padmavathi,Chikhale, Rupesh,Tajne, Madhukar
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p. 437 - 449
(2018/04/20)
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- Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids
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An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.
- Dalvi, Bhakti A.,Lokhande, Pradeep D.
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supporting information
p. 2145 - 2149
(2018/05/08)
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- An Electrophilic Bromine Redox Catalysis for the Synthesis of Indole Alkaloid Building Blocks by Selective Aliphatic C?H Amination
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A new homogeneous bromine(?I/I) redox catalysis is described, which is based on monomeric bromine(I) compounds containing transferable phthalimidato groups. These catalysts enable intermolecular C?H amination reactions at previously unaccessible aliphatic positions and thus enlarge the synthetic potential of direct C?N bond formation, including its application in the synthesis of alkaloid building blocks. This aspect is demonstrated by a new synthetic approach to aspidospermidine. In addition to the development of the catalyst system, the structures of the involved bromine(I) key catalysts were fully elucidated, including by X-ray analyses.
- Bergès, Julien,García, Belén,Mu?iz, Kilian
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supporting information
p. 15891 - 15895
(2018/11/23)
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- Microwave-Assisted Rapid One-Pot Synthesis of Fused and Non-Fused Indoles and 5-[18F]Fluoroindoles from Phenylazocarboxylates
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Substituted indoles can be prepared from phenylazocarboxylates through a rapid one-pot sequence featuring a microwave-assisted Fischer indole synthesis as a key step. Considering that the phenylazocarboxylates may beforehand be modified by mild nucleophilic aromatic substitution, including the introduction of [18F]fluoride, the overall strategy offers an attractive new access to 5-[18F]fluoroindoles.
- Krüll, Jasmin,Hubert, Anja,Nebel, Natascha,Prante, Olaf,Heinrich, Markus R.
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supporting information
p. 16174 - 16178
(2017/10/30)
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- Synthesis of tricyclic units of indole alkaloids: Application of Fischer indolization and olefin metathesis
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Simple synthetic approaches to pyridocarbazole and azepinocarbazole derivatives have been reported via Fischer indolization, Grignard reaction and olefin metathesis as key steps. In addition, a combination Sonogashira coupling and Pauson-Khand reaction has been used to assemble extended pyridocarbazole derivative.
- Kotha, Sambasivarao,Aswar, Vikas R.,Singhal, Gaurav
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p. 6436 - 6442
(2017/10/09)
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- A diversity-oriented approach to indolocarbazoles: Via Fischer indolization and olefin metathesis: Total synthesis of tjipanazole D and i
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New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.
- Kotha, Sambasivarao,Saifuddin, Mohammad,Aswar, Vikas R.
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p. 9868 - 9873
(2016/10/31)
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- Method for preparing indole compounds through catalysis of ionic liquid
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The invention relates to a green synthesis method of one type of indole derivatives. The method is characterized by taking sulfonic acid ionic liquid as a catalyst, taking aliphatic ketone, aromatic ketone and aromatic hydrazine hydrochloride as raw materials, reacting in water, filtering and drying a reaction mixture to obtain indole compounds. The method is simple to operate; the raw materials are low intoxicity and low in costs; the reaction condition is mild; the product is easy to separate; the synthesis process is environmentally-friendly; the indole compounds are high in purity; the catalyst can be directly reused without treatment; the method is green and environmentally-friendly, and is suitable for industrial production.
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Paragraph 0049-0051
(2018/02/04)
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- Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine
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Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-Hamination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N-heterocyclization process are reported.
- Tong, Shuo,Xu, Zhengren,Mamboury, Mathias,Wang, Qian,Zhu, Jieping
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p. 11809 - 11812
(2015/10/05)
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- Inhibiting NF-κB-inducing kinase (NIK): Discovery, structure-based design, synthesis, structure-activity relationship, and co-crystal structures
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The discovery, structure-based design, synthesis, and optimization of NIK inhibitors are described. Our work began with an HTS hit, imidazopyridinyl pyrimidinamine 1. We utilized homology modeling and conformational analysis to optimize the indole scaffol
- Li, Kexue,McGee, Lawrence R.,Fisher, Ben,Sudom, Athena,Liu, Jinsong,Rubenstein, Steven M.,Anwer, Mohmed K.,Cushing, Timothy D.,Shin, Youngsook,Ayres, Merrill,Lee, Fei,Eksterowicz, John,Faulder, Paul,Waszkowycz, Bohdan,Plotnikova, Olga,Farrelly, Ellyn,Xiao, Shou-Hua,Chen, Guoqing,Wang, Zhulun
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p. 1238 - 1244
(2013/03/28)
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- Improved indole syntheses from anilines and vicinal diols by cooperative catalysis of ruthenium complex and acid
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By developing a new and efficient dinuclear catalyst [Ru(CO) 2(Xantphos)]2 [Xantphos = 4,5-bis(diphenylphosphino)-9,9- dimethyl-9H-xanthene], an improved synthesis of indole from vicinal diols and anilines by cooperative catalysis of ruthenium complex and p-TSA (para-toluenesufonic acid) has been demonstrated. The presented synthetic protocol allows assembling a wide range of products in an efficient manner. Comparing to the existed protocols, our indole syntheses can be achieved at lower reaction temperature, in shorter reaction time, and with improved substrate tolerance.
- Zhang, Min,Xie, Feng,Wang, Xiaoting,Yan, Fengxia,Wang, Ting,Chen, Mengmeng,Ding, Yuqiang
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p. 6022 - 6029
(2013/05/09)
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- Fischer indole synthesis in low melting mixtures
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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.
- Gore, Sangram,Baskaran, Sundarababu,K?nig, Burkhard
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supporting information
p. 4568 - 4571
(2012/10/30)
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- Novel SO3H-functionalized ionic liquids catalyzed a simple, green and efficient procedure for Fischer indole synthesis in water under microwave irradiation
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Novel SO3H-functionalized ionic liquids were successfully applied as catalysts for one-pot Fischer indole synthesis under microwave irradiation and in a water medium. Various types of indoles were prepared using single-carbonyl ketones/aldehydes or cyclohexandiones with aryhydrazine hydrochlorides in 86-96% yields in water under microwave irradiation. The indole products could be conveniently separated from the reaction mixture through filtration, and the catalytic system of [(HSO3-p)2im] [CF3SO3]/H2O could be reused directly without any treatment. The entire process is simple, time saving, and environmentally friendly.
- Li, Bai Lin,Zhong, Ai Guo,Xu, Dan-Qian
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p. 45 - 50,6
(2020/10/15)
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- Enantioselective N-H functionalization of indoles with α,β- unsaturated γ-lactams catalyzed by chiral Bronsted acids
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Nitrogen revives: Cyclic N-acyliminium ions were generated from α,β-unsaturated γ-lactams (1) and underwent intermolecular addition by indole nucleophiles (2) under the catalysis of a chiral Bronsted acid (3). A variety of N-functionalized indole derivatives containing a pyrrolidinone moiety (4) were assembled with high enantioselectivity. Bn=benzyl. Copyright
- Xie, Yinjun,Zhao, Yingwei,Qian, Bo,Yang, Lei,Xia, Chungu,Huang, Hanmin
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supporting information; experimental part
p. 5682 - 5686
(2011/08/03)
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- One-pot-one-step, microwave-assisted Fischer indole synthesis
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The Fischer indole synthesis was carried out using microwaves instead of conventional heating procedures. When the mixture of phenylhydrazine, cyclohexanone and zinc chloride was irradiated at 600 W for 3 min, 76% of 1,2,3,4-tetrahydrocarbazole was obtained. However, when zinc chloride was replaced with p-toluenesulfonic acid (p-TSA), the reaction yielded 91% of 1,2,3,4-tetrahydrocarbazole. Thus, a series of indoles were prepared using microwaves in the presence of p-TSA catalyst.
- Creencia, Evelyn Cuevas,Tsukamoto, Masayuki,Horaguchi, Takaaki
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experimental part
p. 1095 - 1102
(2011/11/04)
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- Synthesis and reactions of 4-hydroxy-8,9,10, 11-tetrahydropyrido[3,2,1-jk] carbazol-6-ones
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(Chemical Equation Presented) Tetrahydrocarbazoles 4 obtained from phenylhydrazines and cyclohexanones gave by cyclocondensation with 2-substituted malonates 5 in all cases 4-hydroxy-8,9,10,11-tetrahydropyrido [3,2,1-jk]carbazol-6-ones 6 by attack at the nitrogen and the aromatic ring of tetrahydrocarbazoles 4; the direction of the cyclization was not dependent on substituents either in the aromatic or the saturated ring; isomeric pyridocarbazoles could not be isolated. Electrophilic substitutions of pyridocarbazoles 6 under mild conditions took place exclusively at the 5-position and gave pyridocarbazolediones 9-11 with 5-nitro-, 5-hydroxy or 5-chloro-substituents. Exchange of the chloro substituent in 11 gave 5-azido- and 5-amino products 12, 14 or 16. Reactions at the aromatic ring were not observed. Chlorination of 4-hydroxypyridocarbazoles 6 with phosphoryl chloride by nucleophilic substitution took place exclusively at the 4-position and gave 4-chloropyridocarbazolones 17, which were further reacted to azides and amines 18, 19.
- Stadlbauer, Wolfgang,Van Dang, Hoai,Berger, Birgit S.
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experimental part
p. 807 - 824
(2010/08/20)
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- Fischer indole synthesis catalyzed by novel SO3H-functionalized ionic liquids in water
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Novel SO3H-functionalized ionic liquids bearing two alkyl sulfonic acid groups in the imidazolium cations were designed and successfully applied as catalysts for the one-pot Fischer indole synthesis in water medium. The sequence of the catalytic activity observed in the transformation was in good agreement with the Bronsted acidity order determined by the Hammett method. Various types of indoles from single-carbonyl ketones/aldehydes and cyclohexandiones were provided in 68-96% yields using the catalytic system of [(HSO3-p)2im][HSO4]/H2O. The indole products could be conveniently separated from the reaction mixture by filtration and the dissolved catalyst could be regenerated by treatment with a strongly acidic cation exchange resin, which meant the whole process was performed in water without using any organic solvents.
- Xu, Dan-Qian,Wu, Jian,Luo, Shu-Ping,Zhang, Ji-Xu,Wu, Jia-Yi,Du, Xiao-Hua,Xu, Zhen-Yuan
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supporting information; experimental part
p. 1239 - 1246
(2010/04/26)
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- Bismuth nitrate promoted fischer indole synthesis: A simple and convenient approach for the synthesis of alkyl indoles
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A novel one-pot fisher indole synthesis approach has been developed by using bismuth nitrate as a catalyst. Yields around 90-95% were obtained after reaction in methanol at reflux temperature in 20-40 min. Apart from the mild reaction conditions of the process and its excellent results, the simplicity of product isolation and the possibility to recycle the bismuth nitrate offers a significant advantage.
- Sudhakara, Aralihalli,Jayadevappa, Honnali,Kumar, Hosanagara N.H.,Mahadevan, Kittappa M.
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scheme or table
p. 159 - 164
(2010/04/23)
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- HEPATITIS C VIRUS ENTRY INHIBITORS
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The present invention relates to the use of tricyclic diphenylamine derivative compounds for prevention and/or treatment of Hepatitis C virus (HCV) infection by inhibiting HCV entry into permissive cells.
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Page/Page column 68
(2010/11/30)
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- Microwave-assisted one-pot synthesis of 1,2,3,4-tetrahydrocarbazoles
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A series of 1,2,3,4-tetrahydrocarbazoles 3a-m were synthesized by the reaction of substituted 2-bromocyclohexanones 2a-c with appropriate anilines 1a-i under microwave irradiation without any other catalysts. Copyright Taylor & Francis Group, LLC.
- Chen, Jing,Hu, Yongzhou
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p. 1485 - 1494
(2007/10/03)
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- Indole derivatives process for their preparation, pharmaceutical compositions containing them and their medicinal application
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A chemical compound of formula (I) wherein: R1and R2are independently selected from hydrogen and alkyl; R3is alkyl; R4, R6and R7are independently selected from hydrogen, halogen, hydroxy, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsufoxyl, alkylsulfonyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; R5is selected from hydrogen, halogen, hydroxy, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsulfoxyl, alkylsulfonyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; A is a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring or a 5- or 6-membered partially unsaturated carbocyclic ring, wherein if A is a 6-membered partially unsaturated carbocyclic ring then at least one of R4to R7is other than hydrogen, and pharmaceutically acceptable salts, addition compounds and prodrugs thereof, and the use thereof in therapy, particularly as an agonist or antagonist of a 5HT receptor, particularly a 5HT2Creceptor, for instance in the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinial disorders; diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity.
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Page/Page column 19
(2010/02/05)
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- The regiospecific Fischer indole reaction in choline chloride· 2ZnCl2 with product isolation by direct sublimation from the ionic liquid
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The Fischer indole synthesis occurs in high yield with one equivalent of the ionic liquid choline chloride·2ZnCl2; exclusive formation of 2,3-disubstituted indoles is observed in the reaction of alkyl methyl ketones, and the products readily sublime directly from the ionic liquid.
- Morales, Raul Calderon,Tambyrajah, Vasuki,Jenkins, Paul R.,Davies, David L.,Abbott, Andrew P.
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p. 158 - 159
(2007/10/03)
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- Fischer indole synthesis in the absence of a solvent
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The traditional Fischer synthesis of indoles has been investigated and it has been shown that the reaction proceeds in good yield in the absence of a solvent.
- Matsumoto, Kiyoshi,Tanaka, Akinori,Yukio, Ikemi,Hayashi, Naoto,Toda, Mitsuo,Bulman, Robert A.
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- Metal-catalyzed arylations of hydrazines, hydrazones, and related substrates
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A method is provided for the transition metal-catalyzed arylation, or vinylation, of hydrazines, hydrazones, and the like. Additionally, the invention provides a conceptually novel strategy, the cornerstone of which is the transition metal-catalyzed aryla
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- Chloroaluminate ionic liquid for Fischer indole synthesis
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The Fischer indole synthesis of different ketones using chloroaluminate ionic liquid as a solvent as well as a catalyst is described.
- Rebeiro,Khadilkar
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p. 370 - 372
(2007/10/03)
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- Pyridocarbazole derivatives having cGMP-PDE inhibitory activity
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PCT No. PCT/JP97/01829 Sec. 371 Date Jan. 29, 1998 Sec. 102(e) Date Jan. 29, 1998 PCT Filed May 29, 1997 PCT Pub. No. WO97/45427 PCT Pub. Date Dec. 4, 1997The invention relates to novel pyridocarbazole derivatives having highly selective action in inhibiting cyclic GMP-phosphodiesterase (hereinafter abbreviated as cGMP-PDE), processes for producing such derivatives, agents containing at least one of such derivatives as an active ingredient for preventing and/or treating pulmonary hypertension, ischemic heart diseases or diseases against which the cGMP-PDE inhibitory action is effective, and intermediates useful for the production of pyridocarbazole derivatives.
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- A palladium-catalyzed method for the preparation of indoles via the Fischer indole synthesis
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A Pd-catalyzed method for the preparation of N-aryl benzophenone hydrazones 4 is described. The use of a Pd/BINAP-based catalyst provides hydrazones 4 in good yields. Using 0.1 mol % of a Pd/9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (Xantphos) cata
- Wagaw, Seble,Yang, Bryant H.,Buchwald, Stephen L.
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p. 10251 - 10263
(2007/10/03)
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- Unexpected Debenzylation of N-Benzylindoles with Lithium Base. A New Method of N-Debenzylation
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The reaction of N-benzylindoles with lithium base resulted in debenzylation.The key step would be generation of benzyl carbene from the preformed N-benzyl anion.This reaction should serve as a new debenzylation method for indoles and related compounds.
- Suzuki, Hideharu,Tsukuda, Akiko,Kondo, Mika,Aizawa, Miki,Senoo, Yumiko,et al.
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p. 1671 - 1672
(2007/10/02)
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- Mechanism of Fischer Reaction. Dependence of Thermal Indolization of Cyclohexanone Arylhydrazones on Nature of Substituent in the Benzene Ring
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The kinetics of the Fischer thermal indolization of monosubstituted cyclohexanone arylhydrazones was studied by the spectrophotometric method.The enthalpy and entropy of activation of the reaction were calculated.The data obtained were interpreted in terms of a consistent mechanism of formation of a carbon-carbon bond (the -sigmatropic shift).It was found that the influence of the electronic factors on the rate of the sigmatropic rearrangement is inappreciable.
- Przheval'skii, N. M.,Kostromina, L. Yu.,Grandberg, I. I.
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p. 154 - 158
(2007/10/02)
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- Process of preparing nitrodihydroaryl carbonyl compounds
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Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.
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- Ruthenium Complex Catalyzed N-Heterocyclization. Syntheses of Quinolines and Indole Derivatives from Aminoarenes and 1,3-Propanediol of Glycols
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Aniline reacts with 1,3-propanediol under reflux in diglyme with spontaneous hydrogen evolution in the presence of a catalytic amount of ruth enium trichloride hydrate ( RuCl3*nH2O)-tributylphosphine (PBu3) to give quinoline in good yield.The yield of quinoline was markedly affected by the molar ratios of aniline to 1,3-propanediol and PBu3 to RuCl3*nH2O.The best yield (76percent) was achieved at the molar ratios of 2.5 of aniline / 1,3-propanediol and 2.0 of PBu3 / RuCl3*nH2O.Also, N-substituted anilines react with ethylene glycol in the presence of a catalytic amount of dichlor otris(triphenylphosphine)ruthenium (RuCl2(PPh3)3) to give N-substituted indole derivatives.The reactions were carried out at 180 deg C in dioxane with spontaneus hydrogen evolution.Aminoarenes also react with 2,3-butanediol and 1,2-cyclohexanediol ( mixture of cis and trans ) in the presence of RuCl2(PPh3)3 to give the corresponding 2,3-dimethylindoles and 1,2,3,4-tetrahydrocarbazoles in good to excellent yields.As the key intermediates of the reactions, N,N'-diarylpropylenediamine (5a) and N,N'-diarylethylenediamine (5b) and their dehydrogenated imine derivatives are postulated.
- Tsuji, Yasushi,Huh, Keun-Tae,Watanabe, Yoshihisa
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p. 1673 - 1680
(2007/10/02)
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- MECHANISM OF THE FISCHER INDOLE SYNTHESIS. QUANTUM-CHEMICAL INTERPRETATION OF THE REARRANGEMENT OF SUBSTITUTED CYCLOHEXANONE ARYLHYDRAZONES TO TETRAHYDROCARBAZOLES
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Calculations of a number of model structures within the scheme of Fischer indole synthesis were made on the basis of a bonding variant of perturbation theory in the self-consistent-field (SCF) MO LCAO method.A quantum-chemical interpretation of the effect of substituents on the course of the thermal process is given.The kinetics of the thermal and acid-catalyzed indolization of substituted cyclohexanone arylhydrazones to tetrahydrocarbazoles were studied by spectrophotometry.It was shown that the experimental data are in satisfactory agreement with the calculated values. It was concluded that a concerted mechanism ( a -sigma-tropic shift) for the step involving the formation of a carbon-carbon bond in the Fischer reaction is preferred.
- Visotskii, Yu. B.,Przheval'skii, N. M.,Zemskii, B. P.,Grandberg, I. I.,Kostromina, L. Yu.
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p. 713 - 722
(2007/10/02)
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- α-Nitroarylation of Ketones and Esters: An Exceptionally Facile Synthesis of Indoles, 2-Indolinones, and Arylacetic Acids
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Silyl enol ethers and ketene silyl acetals add to aromatic nitro compounds in the presence of fluoride ion sources to give dihydroaromatic nitronates which are readily oxidized to α-nitroaryl carbonyl compounds by DDQ or Br2.These versatile intermediates are readily converted into indoles or 2-indolinones by reductive cyclization.Since halogen substituents on the aromatic ring are not displaced in the initial alkylation reaction, nucleophilic substitution of these groups, followed by functional group manipulations of the nitro group, permits easy access to indoles, 2-indolinones, and arylacetic acids with varied substitution patterns.
- RajanBabu, T. V.,Chenard, Bertrand L.,Petti, Michael A.
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p. 1704 - 1712
(2007/10/02)
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