- Mechanochemical Transformation of CF3 Group: Synthesis of Amides and Schiff Bases
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We communicate two mild, solvent-free mechanochemical coupling transformations of CF3 group with nitro compounds into amides or Schiff bases employing Ytterbia as a catalyst. This process proceeds via C?F bond activation, accompanied with utilisation of Si-based reductants/oxygen scavengers – reductants of the nitro group. The scope and limitations of the disclosed methodologies are thoroughly studied. To the best of our knowledge, this work is the first example of mechanical energy promoted transformation of the inert CF3 group into other functionalities. (Figure presented.).
- Mkrtchyan, Satenik,Jakubczyk, Micha?,Lanka, Suneel,Yar, Muhammad,Ayub, Khurshid,Shkoor, Mohanad,Pittelkow, Michael,Iaroshenko, Viktor O.
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supporting information
p. 5448 - 5460
(2021/10/19)
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- Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring
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Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).
- Qiang-Liu,Liu, Yu-Xiu,Song, Hong-Jian,Wang, Qing-Min
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supporting information
p. 3110 - 3115
(2020/07/04)
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- A indole compound and its preparation method and application (by machine translation)
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The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)
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Paragraph 0131; 0134; 0135
(2018/10/02)
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- Half-sandwich structured ruthenium complex and preparation method thereof, and method for reducing o-nitrobenzene ethanol compound into indole compound
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The invention discloses a half-sandwich structured ruthenium complex and a preparation method thereof, and a method for reducing an o-nitrobenzene ethanol compound into an indole compound. The structure of the ruthenium complex is as shown in formula (A), wherein in the formula (A), X is halogen, R is H, -oxyl, halogen or nitro, and n is a positive integer ranging from 1 to 4. By the adoption of the preparation method, the ruthenium complex with excellent chemical stability can be obtained; meanwhile, the preparation method has the advantages of simple operation, low equipment requirement and batch production; furthermore, the ruthenium complex can be used as a catalyst for catalytically reducing the o-nitrobenzene ethanol compound (Refer to Specification).
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Paragraph 0080; 0089
(2017/07/22)
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- Alcohol-Enhanced Cu-Mediated Radiofluorination
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The potential of many 18F-labeled (hetero)aromatics for applications in positron emission tomography remains underexplored because convenient procedures for their radiosynthesis are lacking. Consequently, simple methods to prepare radiofluorinated (hetero)arenes are highly sought after. Herein, we report the beneficial effect of primary and secondary alcohols on Cu-mediated 18F-labeling. This observation contradicts the assumption that such alcohols are inappropriate solvents for aromatic fluorination. Therefore, we developed a protocol for rapid radiolabeling of an extraordinarily broad scope of boronic and stannyl substrates under general reaction conditions. Notably, radiofluorinated indoles, phenols, and anilines were synthesized directly from the corresponding unprotected precursors. Furthermore, the novel method enabled the preparation of radiofluorinated tryptophans, [18F]F-DPA, [18F]DAA1106, 6-[18F]FDA, and 6-[18F]FDOPA.
- Zischler, Johannes,Kolks, Niklas,Modemann, Daniel,Neumaier, Bernd,Zlatopolskiy, Boris D.
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supporting information
p. 3251 - 3256
(2017/03/17)
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- METHOD FOR PRODUCING 4-FLUOROISATIN DERIVATIVE
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PROBLEM TO BE SOLVED: To provide a method for producing a 4-fluoroisatin derivative including 4-fluoroisatin at high purity and at high yield. SOLUTION: Provided is a method for producing a 4-fluoroisatin, in a production process of a 4-fluoroisatin derivative represented by general formula (1), comprising: a step (A) where a toluene derivative represented by the general formula (2) is used as starting raw material, the toluene derivative is carbon-increased using DMFdialkylacetal, and thereafter, reduction is performed using a reducing agent and acid to synthesize an indol derivative represented by general formula (3); and a step (B) where the indol derivative is oxidized. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0026; 0071; 0076; 0079; 0085
(2017/02/09)
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- The synthesis of N-heterocycles via copper/TEMPO catalysed aerobic oxidation of amino alcohols
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N-Heterocycles can be prepared using alcohol oxidation as a key synthetic step. Herein we report studies exploring the potential of Cu/TEMPO as an aerobic oxidation catalyst for the synthesis of substituted indoles and quinolines.
- Flanagan, James C. A.,Dornan, Laura M.,McLaughlin, Mark G.,McCreanor, Niall G.,Cook, Matthew J.,Muldoon, Mark J.
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supporting information; experimental part
p. 1281 - 1283
(2012/06/04)
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- PYRROLE ANTIFUNGAL AGENTS
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The invention provides compounds of formula (I), and pharmaceutically and agriculturally acceptable salts thereof; wherein: R1, R2, R3, R4, R5, R6, A1, L1 and n are as defined herein. These compounds and their pharmaceutically acceptable salts are useful in prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.
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Page/Page column 149-150
(2009/12/05)
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- PIPERIDINYLHYDROXYETHYLPIPERIDINES AS MODULATORS OF CHEMOKINE RECEPTORS
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The present invention relates to a compound of the formula (I), or a pharmaceutically acceptable salt thereof, wherein R1-R8 and X, m, and n are defined. Compounds and compositions of the present invention are useful the treatment of atherosclerosis.
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Page/Page column 19
(2009/05/28)
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- Synthesis and structure of fluoroindole nucleosides
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Chemically modified bases are frequently used to stabilize nucleic acids, to study the driving forces for nucleic acid structure formation, and to tune DNA and RNA hybridization conditions. Nucleoside analogues are chemical means to investigate hydrogen bonds, base stacking, and solvation as the three predominant forces that are responsible for the stability of nucleic acids. To obtain deeper insight into the contributions of these interactions to RNA stability, we decided to synthesize some novel nucleic acid analogues where the nucleobases are replaced by fluoroindoles. Fluorinated indoles can be compared with fluorinated benzimidazoles to determine the role of nitrogen in five-membered ring systems. The synthesis of fluoroindole ribonucleosides as well as the X-ray crystal structures of all synthesized fluoroindole ribonucleosides are reported here. These compounds could also be building blocks for a variety of biologically active RNA analogues.
- Bozilovic, Jelena,Bats, Jan W.,Engels, Joachim W.
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p. 283 - 292
(2008/02/11)
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- Synthesis of fluorinated indoles as RNA analogues
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Nucleoside analogues are chemical means to investigate hydrogen bonds, base stacking, and solvation as the three predominant forces that are responsible for the stability of secondary structure of nucleic acids. To obtain deeper insight into the contributions of these interactions to RNA stability apart from the ones exerted by the predominant nucleosides we decided to synthesize some novel nucleic acid analogues where the nucleobases are replaced by fluoroindoles. Fluorinated indoles can be compared to fluorinated benzimidazoles to determine the role of nitrogen in five membered ring system. The synthesis of fluoroindole ribonucleosides is described here. Copyright Taylor & Francis Group, LLC.
- Bozilovic, Jelena,Engels, Joachim W.
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p. 869 - 871
(2008/03/27)
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- In search of simplicity and flexibility: A rational access to twelve fluoroindolecarboxylic acids
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All twelve indolecarboxylic acids 1-12 carrying both a fluorine substituent and a carboxy group at the benzo ring have been prepared either directly from the corresponding fluoroindoles 13-16 or from the chlorinated derivatives 22, 23 and 25 by hydrogen/metal permutation ("metalation"), or from the bromo- or iodofluoroindoles 17-20 and 26, 27, 29 and 30 by halogen/metal permutation, the organometallic intermediate being each time trapped with carbon dioxide. In most, though not all cases, the nitrogen atom in the five-membered ring had to be protected by a trialkylsilyl group. Some of the bromo- or iodofluoroindoles (26 and 27) were successfully subjected to a basicity gradient-driven selective migration of the heavy halogen. An unexpected finding on the way to the target compounds were the rigorously site-selective metalation of the 5-fluoro-N-(trialkylsilyl)indole (14b; exclusive deprotonation of the 4-position). The fluoroindoles 13-16, although previously known, were accessed more conveniently from suitably substituted nitrobenzenes using the Bartoli or the Leimgruber-Batcho method. A new and very attractive indole synthesis was elaborated consisting of the ortho-lithiation of an N-acyl-protected aniline followed by ortho-formylation, Wittig chloromethylenation and base-catalyzed cyclization accompanied by dehydrochlorination. These five consecutive steps can be contracted to a convenient one-pot protocol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Schlosser, Manfred,Ginanneschi, Assunta,Leroux, Frederic
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p. 2956 - 2969
(2007/10/03)
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- Microwave assisted Leimgruber-Batcho reaction for the preparation of indoles, azaindoles and pyrroylquinolines
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The development of enhanced conditions for Lewis acid catalysed Leimgruber-Batcho indole synthesis using microwave acceleration is described. This approach has permitted the preparation of a variety of heteroaromatic enamine intermediates in good yield and high purities. Subsequent catalytic hydrogenation reactions, under various conditions including the use of a solid-phase encapsulated catalyst, furnish the corresponding indole derivatives in good yields.
- Siu, Jason,Baxendale, Ian R.,Ley, Steven V.
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p. 160 - 167
(2007/10/03)
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- A novel fluorinated tryptamine with highly potent serotonin 5-HT1A receptor agonist properties
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Synthesis and biological evaluation of a novel fluorinated tryptamine analogue are described. This new compound 1-(4-fluoro-5-methoxyindol-3-yl)pyrrolidine (2) was found to be a potent serotonin 5-HT1A agonist.
- Laban, Uros,Kurrasch-Orbaugh, Deborah,Marona-Lewicka, Danuta,E. Nichols, David
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p. 793 - 795
(2007/10/03)
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- SIMPLE SYNTHESIS OF 1-(AZACYCLOALKYL)INDOLES USING EXCLUSIVE ORTHO α-CHLOROACETYLATION OF N-(AZACYCLOALKYL)ANILINES
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Use of 2-(azacycloalkyl)amino-α-chloroacetophenones (4) as starting material makes possible simple synthesis of 1-(azacycloalkyl)indoles (2).
- Sasakura, Kazuyuki,Adachi, Makoto,Sugasawa, Tsutomu
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p. 265 - 274
(2007/10/02)
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- Silica Gel Assisted Reductive Cyclization of 2-Nitro-β-piperidinostyrenes, Derived from 2-Nitrotoluenes, to Indoles
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An efficient modification of the Leimgruber-Batcho method of indole synthesis has been devised that facilitates the synthesis of a variety of 2,3-unsubstituted indoles containing halogen, methoxy and benzyloxy groups, from 2-nitrotoluenes, in high yields.The modified method involves the condensation of 2-nitrotoluenes with tripiperidinomethane followed by the reductive cyclization of the intermediate 2-nitro-β-piperidinostyrenes with iron and acetic acid in refluxing toluene in the presence of silica gel (column chromatography grade, 60-200 mesh).
- Kawase, Masami,Sinhababu, Achintya K.,Borchardt, Ronald T.
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p. 1499 - 1501
(2007/10/02)
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