- Formation of 3H-1,3-Benzodiazepines from Quinoline N-Acylimides
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Photolysis of the quinoline N-imides (3) having an electron-donating substituent in the 6- or 8-position affords the corresponding 3H-1,3-benzodiazepines (4), whereas quinolines having an electron-donating group in the other positions or an electron-withd
- Tsuchiya, Takashi,Okajima, Satoru,Enkaku, Michiko,Kurita, Jyoji
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- Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate
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Transition-metal-catalyzed C-H activation and subsequent oxidative cyclization with alkynes has been a powerful tool for the synthesis of polycyclic aromatic compounds. Despite the substantial progress in this field, it is still a significant challenge to establish synthetic methodologies for the construction of nonsubstituted vinylene-fused aromatics. We herein report a Rh(III)-catalyzed C-H/N-H annulation with vinylene carbonate as an acetylene surrogate. Vinylene carbonate also acts as an internal oxidant to regenerate the Rh(III) species in situ; thus, no external oxidant is required to trigger the oxidative annulation. This protocol is applicable to the direct synthesis of various N-heteroaromatics.
- Ghosh, Koushik,Nishii, Yuji,Miura, Masahiro
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p. 11455 - 11460
(2019/12/02)
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- Na 2 CO 3-Catalyzed N-Acylation of Indoles with Alkenyl Carboxylates
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The N-acylation of indoles has been accomplished via inorganic base catalysis. It provided an efficient and simple catalysis system for the preparation of N-acylindoles with alkenyl carboxylates as acylating agents. A broad variety of indoles undergo the smooth N-acylation using Na 2 CO 3 as catalyst in MeCN at 120? °C to give the corresponding N-acylindoles in good to excellent yields.
- Zhou, Xiao-Yu,Chen, Xia
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supporting information
p. 516 - 521
(2019/01/10)
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- Based on carboxylic acid allyl ester as the acylation reagent N - acyl indoles preparation method (by machine translation)
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Based on carboxylic acid allyl ester as the acylation reagent N - acyl indoles preparation method, which belongs to the medical and chemical intermediates and related chemical technical field. This method uses the indole compounds and carboxylic acid allyl ester as the raw material, in the catalysis of alkali, realizes the N - acyl indoles of green, efficient synthesis. The method has high selectivity, mild reaction conditions, functional group compatibility is good, wide substrate range, environment-friendly and the like. Because the N - acyl indoles is an important organic synthetic intermediates, in organic synthesis and in the field of pharmacy has very wide application, therefore, the invention has great application value and social and economic benefits. (by machine translation)
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Paragraph 0053-0055
(2018/12/02)
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- Ring-Opening of Indoles: An Unconventional Route for the Transformation of Indoles to 1 H-Pyrazoles Using Lewis Acid
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An unusual transformation of indoles to pyrazoles via an aromatic ring-opening strategy has been developed. The salient feature of this strategy involves the C2-N1 bond opening and concomitant cyclization reaction of the C2=C3 bond of the indole moiety with the tosylhydrazone, which proceeds under transition-metal and ligand free conditions. This ring-opening functionalization of indoles provides a wide scope of differently substituted pyrazoles.
- Panda, Subhankar,Pradhan, Nirmalya,Manna, Debasis
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supporting information
p. 573 - 578
(2018/09/25)
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- Intermolecular dearomative C2-arylation of N-Ac indoles activated by FeCl3
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We report the FeCl3-mediated direct addition of electron-rich arenes to the C2-position of electrophilic N-Ac indoles under mild conditions (room temperature, air). No functional group is required on the arene nucleophile: one of its C-H bonds is added to the C2=C3 double bond of the indole nucleus in a Friedel-Crafts-type reaction. This dearomatisation process delivered a broad range of C2-arylated indolines.
- Nandi, Raj Kumar,Ratsch, Friederike,Beaud, Rodolphe,Guillot, Régis,Kouklovsky, Cyrille,Vincent, Guillaume
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p. 5328 - 5331
(2016/04/26)
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- Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles
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Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.
- Morimoto, Naoki,Morioku, Kumika,Suzuki, Hideyuki,Takeuchi, Yasuo,Nishina, Yuta
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supporting information
p. 2020 - 2023
(2016/06/01)
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- A simple, effective, green method for the regioselective 3-acylation of unprotected indoles
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A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.
- Tran, Phuong Hoang,Tran, Hai Ngoc,Hansen, Poul Erik,Do, Mai Hoang Ngoc,Le, Thach Ngoc
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p. 19605 - 19619
(2015/11/27)
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- A trans diacyloxylation of indoles
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A trans diacyloxylation of indoles is accomplished by employing PhI(OAc)2 as the oxidant. A broad range of functional groups are well tolerated. Both the electronic properties of the N-protecting groups of indoles and the acidity of the reaction media play important roles in the selectivity of indole acyloxylation reactions. The Royal Society of Chemistry 2012.
- Liu, Qiang,Zhao, Qing Yong,Liu, Jie,Wu, Pan,Yi, Hong,Lei, Aiwen
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supporting information; experimental part
p. 3239 - 3241
(2012/04/10)
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- Oxaziridine-mediated oxyamination of indoles: An approach to 3-aminoindoles and enantiomerically enriched 3-aminopyrroloindolines
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A radical solution: A highly regioselective copper(II)-catalyzed oxyamination of N-acyl indoles with oxaziridines gave aminal products that could be converted in a single step into 3-aminoindoles and 3-aminopyrroloindolines (see scheme). When a chiral N-acyl group was used, the core fragment of some architecturally fascinating pyrroloindoline alkaloids was formed with 91% ee. Bs=benzenesulfonyl, Moc=methoxycarbonyl. Copyright
- Benkovics, Tamas,Guzei, Ilia A.,Yoon, Tehshik P.
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supporting information; experimental part
p. 9153 - 9157
(2011/02/19)
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- Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles
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N-Acetylindoles can be oxidatively coupled with arenes such as benzene or pentafluorobenzene in dioxane. The use of Cu(OAc)2 as the stoichiometric oxidant produces selective arylation at the 3-position of indole while AgOAc produces selective a
- Potavathri, Shathaverdhan,Dumas, Ashley S.,Dwight, Timothy A.,Naumiec, Gregory R.,Hammann, Jeffrey M.,DeBoef, Brenton
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p. 4050 - 4053
(2008/09/20)
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- An efficient synthetic method for 2-methoxy-1,2-dihydro-3H-indol-3-ones
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An efficient method for synthesis of 2-methoxy-1,2-dihydro-3H-indol-3- ones using two successive oxidations of indoles is described.
- Kawasaki, Tomomi,Nonaka, Yoshinori,Matsumura, Ken,Monai, Miyuki,Sakamoto, Masanori
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p. 3251 - 3261
(2007/10/03)
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- A Regiocontrolled Synthesis of Substituted Indoles by Palladium-Catalyzed Coupling of 2-Bromonitrobenzenes and 2-Bromoacetanilides
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The palladium-catalyzed cross-coupling reaction of 2-bromonitrobenzenes or 2-bromoacetanilides with ethylene has been used to produce a variety of substituted indoles.The mild reaction conditions and selectivity inherent in the coupling reaction have been utilized to produce regiochemically pure 4-, 5-, 6-, and 7-substituted indoles.
- Kasahara, Akira,Izumi, Taeko,Murakami, Satoshi,Miyamoto, Kazuhiro,Hino, Toshimi
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p. 1405 - 1413
(2007/10/02)
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- Studies on the Syntheses of Heterocyclic Compounds. Part 865. A Novel Synthesis of Indole Derivatives by Intramolecular Nucleophilic Aromatic Substitution
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Cyclisation of N-(2-bromo-4,5-dimethoxyphenethyl)acetamide (6) afforded 1-acetyl-2,3-dihydro-5,6-dimethoxy-1H-indole (13) by intramolecular nucleophilic aromatic substitution using sodium hydride and cuprous halide in dimethylformamide.The dihydroindoles (14), (15), and (16) were also synthesised from the corresponding amides (8) and (10) and the carbamate (12) in a similar manner.The dihydroindoles (13), (14), and (16) were converted into the indoles (20) and (21) in excellent yield by oxidation and subsequent alkaline hydrolysis.The 2-oxindoles (26) and (27) were also prepared under similar reaction condition from the phenylacetamide (24) and (25).
- Kametani, Tetsuji,Ohsawa, Tatsushi,Ihara, Masataka
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p. 290 - 294
(2007/10/02)
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