- Site-Selective Electrochemical C-H Cyanation of Indoles
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An electrochemical approach for the site-selective C-H cyanation of indoles employing readily available TMSCN as cyano source has been developed. The electrosynthesis relies on the tris(4-bromophenyl)amine as a redox catalyst, which achieves better yield and regioselectivity. A variety of C2- and C3-cyanated indoles were obtained in satisfactory yields. The reactions are conducted in a simple undivided cell at room temperature and obviate the need for transition-metal reagent and chemical oxidant.
- Li, Laiqiang,Hou, Zhong-Wei,Li, Pinhua,Wang, Lei
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supporting information
p. 5983 - 5987
(2021/08/16)
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- GaCl3-Catalyzed C-H Cyanation of Indoles with N-Cyanosuccinimide
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An efficient GaCl3-catalyzed direct cyanation of indoles and pyrroles using bench-stable electrophilic cyanating agent N-cyanosuccinimide was achieved and afforded 3-cyanoindoles and 2-cyanopyrroles in good yields and excellent regioselectivities. Notably, this protocol exhibited high reactivity for unprotected indoles and was applicable to a broad range of indole and pyrrole substrates.
- Wang, Xue,Makha, Mohamed,Chen, Shu-Wei,Zheng, Huaiji,Li, Yuehui
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p. 6199 - 6206
(2019/05/24)
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- A facile and efficient synthesis of 3-cyanoindoles by a simple palladium(II)-catalyzed C─H activation of indoles
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An efficient trans-PdCl2(NH2CH2COOH)2-catalyzed direct C3-cyanation of indole C─H bonds is described. Notably, free (N─H)-indoles reacted smoothly using the procedure, and the desired product 3-cyanoindoles were obtained in good to excellent yields.
- Chu, Hailiang,Guo, Mengping,Yi, Yanping,Wen, Yongju,Zhou, Lanjiang,Huang, Hongwei
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- Indole cyanation via CH bond activation under catalysis of Ru(III)-exchanged NaY zeolite (RuY) as a recyclable catalyst
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Selective 3-cyanation of indoles was achieved under heterogeneous catalysis of Ru(III)-exchanged NaY zeolite (RuY) as a recyclable catalyst, in combination with K4[Fe(CN)6] as a nontoxic, slow cyanide releasing agent. Under the aforementioned conditions, good yields of the desired products were obtained.
- Khorshidi, Alireza
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experimental part
p. 903 - 906
(2012/08/28)
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- Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS)
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BF3?OEt2-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.
- Yang, Yang,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 5608 - 5611
(2011/12/03)
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- Direct transformation of N, N -dimethylformamide to -CN: Pd-catalyzed cyanation of heteroarenes via C-H functionalization
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This paper describes the direct cyanation of indoles and benzofurans employing N,N-dimethylformamide (DMF) as both reagent and solvent. Isotopic labeling experiments indicated that both the N and the C of the cyano group derived from DMF. This transformation offers an alternative method for preparing aryl nitriles, though it is currently limited in scope to indoles and benzofurans.
- Ding, Shengtao,Jiao, Ning
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supporting information; experimental part
p. 12374 - 12377
(2011/10/02)
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- The palladium-catalyzed cyanation of indole C-H bonds with the combination of NH4HCO3 and DMSO as a safe cyanide source
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A palladium-catalyzed cyanation of the 3-position of indole sp2 C-H bonds by the combination of NH4HCO3 and DMSO as the "CN" source was achieved to provide aromatic nitriles in moderate to good yields with excellent regioselectivity. It represents a practical and safe cyanation method.
- Ren, Xinyi,Chen, Jianbin,Chen, Fan,Cheng, Jiang
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experimental part
p. 6725 - 6727
(2011/07/07)
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- Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere via N-H imines as an intramolecular directing group
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Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.
- Zhang, Line,Ang, Gim Yean,Chiba, Shunsuke
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supporting information; experimental part
p. 1622 - 1625
(2011/05/05)
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- BENZOXAZINONE DERIVATIVES FOR THE TREATMENT OF GLYTL MEDIATED DISORDERS
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The present invention relates to benzoxazinone derivatives, processes for their preparation, pharmaceutical compositions and medicaments containing them and to their use in treating disorders mediated by GlyT1, including neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder.
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Page/Page column 78
(2011/02/24)
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- Palladium-catalyzed direct cyanation of indoles with K4[Fe(CN) 6]
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"Chemical equation presented" Direct cyanation of Indole derivatives has been achieved with nontoxic K4[Fe(CN)6] as cyanating agent through Pd-catalyzed C-H bond activation.
- Yan, Guobing,Kuang, Chunxiang,Zhang, Yan,Wang, Jianbo
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scheme or table
p. 1052 - 1055
(2010/06/13)
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- A facile synthesis of 1-phenylsulfonyl-3-substituted-2-cyanoindoles, 1-phenylsulfonyl-2-methyl-3-cyanoindoles, and bifunctional 1- phenylsulfonylindoles
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A facile 'one-pot' introduction of the cyano group into the 2/3-position of indole has been developed from the corresponding aldehydes using anhydrous aluminum chloride and sodium azide. Georg Thieme Verlag Stuttgart.
- Jaisankar, Pichamuthu,Srinivasan
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p. 2413 - 2417
(2008/03/13)
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- Isocyanatophosphoric acid dichloride: A novel reagent for the introduction of a cyano group into the molecules of electron-rich heterocycles and enamines
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A new synthetic method is developed which enables a direct one-step introduction of a cyano group into electron-rich heterocyclic systems of the indole, pyrrole, and indolizine series, and also to enamines using isocyanatophosphoryl dichloride.
- Smaliy, Radomir V.,Chaikovskaya, Aleksandra A.,Pinchuk, Aleksandr M.,Tolmachev, Andrei A.
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p. 2416 - 2420
(2007/10/03)
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- Azide Ring-Opening-Ring-Closure Reactions and Tele-substitutions in Vicinal Azidopyrazole-, Pyrrole- and Indolecarboxaldehydes
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5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3.Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields.Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields.In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.
- Becher, Jan,Joergensen, Per Lauge,Pluta, Krystian,Krake, Niels J.,Faelt-Hansen, Birgitte
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p. 2127 - 2134
(2007/10/02)
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- Heterocyclic Rearrangements. Phenylhydrazones and N-Methyl-N-phenylhydrazones of 3-Acylisoxazoles
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The reaction of 3-benzoyl-5-phenylisoxazole (4) and 3-acetyl-5-methylisoxazole (5) with phenylhydrazine and N-methyl-N-phenylhydrazine has been investigated and the reactivity of (E)- and (Z)-phenylhydrazones and N-methyl-N-phenylhydrazones has been studied.
- Vivona, Nicolo,Macaluso, Gabriella,Frenna, Vincenzo,Ruccia, Michele
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p. 931 - 934
(2007/10/02)
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- Cyanation using the Combined Reagent, Triphenylphosphine-Thiocyanogen (TPPT): A New General Route to Indole and Pyrrole Carbonitriles
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Various types of indoles, pyrroles, and enamines react with the combined reagent, Ph3P-(SCN)2 (TPPT) under mild conditions to give the corresponding cyanated compounds in high yields.The reaction mechanism of the cyanation is discussed.
- Tamura, Yasumitsu,Adachi, Masahiro,Kawasaki, Tomomi,Yasuda, Hitoshi,Kita, Yasuyuki
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p. 1132 - 1135
(2007/10/02)
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