- Synthesis of 3-nitroindoles by sequential paired electrolysis
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3-Nitroindoles are synthetically versatile intermediates but current methods for the preparation hinder their widespread application. Herein, we report that nitroenamines undergo electrochemical cyclisation to 3-nitroindoles in the presence of potassium iodide. Detailed control experiments and cyclic voltammogram studies infer the reaction proceedsviaa sequential paired electrolysis process, beginning with anodic oxidation of iodide (I?) to the iodine radical (I˙), which facilitates cyclisation of the nitroenamine to give a 3-nitroindolinyl radical. Cathodic reduction and protonation generates a 3-nitroindoline that upon oxidation forms the 3-nitroindole.
- Lindsay, Ashley C.,Kilmartin, Paul A.,Sperry, Jonathan
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p. 7903 - 7913
(2021/09/28)
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- NaNO2/K2S2O8-mediated Selective Radical Nitration/Nitrosation of Indoles: Efficient Approach to 3-Nitro- and 3-Nitrosoindoles
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JPZ acknowledges financial support from the National Natural Science Foundation of China (No. 21172163, 21472133), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1749). (Figure presented.).
- Shoberu, Adedamola,Li, Cheng-Kun,Tao, Ze-Kun,Zhang, Guo-Yu,Zou, Jian-Ping
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supporting information
p. 2255 - 2261
(2019/04/13)
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- Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions
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An efficient, mild, and metal-free approach to direct diazenylation of N-heterocyclic compounds with aryltriazenes using Br?nsted ionic liquid as a promoter has been developed for the first time. Many N-heterocyclic azo compounds were synthesized in good to excellent yields at room temperature under an open atmosphere. Notably, the promoter 1,3-bis(4-sulfobutyl)-1H-imidazol-3-ium hydrogen sulfate could be conveniently recycled and reused with the same efficacies for at least four cycles.
- Cao, Dawei,Zhang, Yonghong,Liu, Chenjiang,Wang, Bin,Sun, Yadong,Abdukadera, Ablimit,Hu, Haiyan,Liu, Qiang
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p. 2000 - 2003
(2016/06/01)
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- Method for preparing nitroindole derivatives
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The invention discloses a method for preparing nitroindole derivatives. The method comprises the following steps: dissolving indole derivatives, sodium nitrate and potassium persulfate in a solvent, and reacting at 60-100 DEG C to obtain the nitroindole d
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Paragraph 0023
(2016/10/31)
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- Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: Dehydrogenative access to 3-nitroindoles
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We describe here a new metal-free route for the synthesis of 3-nitroindoles by the nitrative cyclization of N-aryl imines with tert-butyl nitrite. The radical transformation allows the assembly of the indole framework through oxidative cleavage of multi C-H bonds, a nitration, cyclization and isomerization cascade.
- Deng, Guo-Bo,Zhang, Jia-Ling,Liu, Yan-Yun,Liu, Bang,Yang, Xu-Heng,Li, Jin-Heng
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supporting information
p. 1886 - 1888
(2015/02/05)
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- Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling
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A variety of N-aryl β-nitroenamines were effectively transformed into 3-nitroindoles in good yields and with complete regioselectivity via a rapid microwave (μW) assisted intramolecular arene-alkene coupling reaction. This report further demonstrates the versatility of this method by constructing 3-carboalkoxy-and 3-cyanoindoles. Optimization data, substrate scope, and applications are discussed.
- Nguyen, Huy H.,Kurth, Mark J.
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supporting information
p. 362 - 365
(2013/03/13)
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- Nucleophilic addition of hetaryllithium compounds to 3-Nitro-1- (phenylsulfonyl)indole: Synthesis of tetracyclic thieno[3,2-c]-δ- carbolines
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3-Nitro-1-(phenylsulfonyl)indole undergoes addition of aryl- and hetaryllithium nucleophiles to produce 2-substituted-3-nitroindoles. Mild reductive-acylation provides excellent access to 3-amido-2-hetarylindoles from which new thieno[3,2-c]-δ-carbolines
- Alford, Philip E.,Kishbaugh, Tara L.S.,Gribble, Gordon W.
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experimental part
p. 831 - 840
(2010/09/18)
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- PIDA-mediated oxidative C-C bond formation: Novel synthesis of indoles from n-aryl enamines
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A variety of functionalized indoles were synthesized from N-aryl enamines via PIDA-mediated oxidative carbon-carbon bond formation. The features of the present reaction include facilitative preparation of substrates 2, good functional group tolerance, and mild reaction conditions without transition metals.
- Yu, Wenquan,Du, Yunfei,Zhao, Kang
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supporting information; experimental part
p. 2417 - 2420
(2009/11/30)
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- Design, synthesis, and biological evaluation of substituted-N-(thieno[2,3-b]pyridin-3-yl)-guanidines, N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines
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Sulfonylureas stimulate insulin secretion independent of the blood glucose concentration and therefore cause hypoglycemia in type 2 diabetic patients. Over the last years, a number of aryl-imidazoline derivatives have been identified that stimulate insulin secretion in a glucose-dependent manner. In the present study, we have developed three series of substituted N-(thieno[2,3-b]pyridin-3-yl)-guanidine (2a-l), N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidine (3a-l), and N-(1H-indol-3-yl)-guanidine (4a-l) as new class of antidiabetic agents. In vitro glucose-dependent insulinotropic activity of test compounds 2a-l, 3a-l, and 4a-l was evaluated using RIN5F (Rat Insulinoma cell) based assay. All the test compounds showed concentration-dependent insulin secretion, only in presence of glucose load (16.7 mmol). Some of the test compounds (2c, 3c, and 4c) from each series were found to be equipotent to BL 11282 (standard aryl-imidazoline), which indicated that the guanidine group acts as a bioisostere of imidazoline ring system.
- Bahekar, Rajesh H.,Jain, Mukul R.,Goel, Ashish,Patel, Dipam N.,Prajapati, Vijay M.,Gupta, Arun A.,Jadav, Pradip A.,Patel, Pankaj R.
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p. 3248 - 3265
(2008/02/07)
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- Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent
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The reaction of 2-phenyl- and 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2-CH3COOH) in benzene leads mainly to the formation of the isonitroso and 3-nitroso indole derivatives, respectively. When reacted
- Astolfi, Paola,Panagiotaki, Maria,Rizzoli, Corrado,Greci, Lucedio
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p. 3282 - 3290
(2008/09/17)
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- Glycosidopyrroles. Part 3. Effect of the benzocondensation on acyclic derivatives: 1-(2-hydroxyethoxy) methylindoles as potential antiviral agents
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The new of 1-(2-hydroxyethoxy) methylindole derivatives 3a-i were prepared in good yields. None of them showed any significant anti-HIV activity and therefore the benzocondensation between the 2 and 3 positions of the pyrrole ring definitely reduced the w
- Almerico, Anna Maria,Barraja, Paola,Diana, Patrizia,Cirrincione, Girolamo,Mingoia, Francesco,Musiu, Chiara,Perra, Graziella,Putzolu, Monica,Marongiu, Maria Elena
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p. 409 - 414
(2007/10/03)
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- Electrophilic ipso-Substitutions. Part 1. Reaction of 3-Substituted Indoles with Nitronium and Nitrosonium Ions
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3-Substituted indoles react with nitronium and nitrosonium ions to yield 3-nitroindole.In both cases the reaction was interpreted as an electrophilic ipso-substitution.The reaction mechanism is interpreted by hypothesizing the formation of a ?-complex-like intermediate, wich is some cases is preceded by an electron-transfer process.An order for the leaving abilities of the different electrofugal groups is discussed.
- Colonna, Martino,Greci, Lucedio,Poloni, Marino
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p. 628 - 632
(2007/10/02)
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