- Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach
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An electrochemical synthesis method for the selective N1-acylation of indazoles has been developed. This "anion pool" approach electrochemically reduces indazole molecules generating indazole anions and H2. Acid anhydrides are then introduced to the solution resulting in selective acylation of the N1-position of the indazoles. This procedure can also be applied to the acylation of benzimidazoles and indoles. The reaction can also be performed using a 9 V battery without loss of reaction efficiency.
- DIssanayake, D.M.M. Mevan,Vannucci, Aaron K.
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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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- An effective C-C double bond formation via Cu(I)-catalyzed dehydrogenation
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A dehydrogenation method using Cu(I) and either N,N-di-tert-butylthiadiaziridine 1,1-dioxide or N,N-di-tert-butyldiaziridinone is reported. The dehydrogenation allows a facile introduction of C-C double bond(s) into various carbocycles and heterocycles such as oxazolines and thiazolines.
- Ramirez, Thomas A.,Zhao, Baoguo,Shi, Yian
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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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- A new, stereoselective, ring-forming reaction of 1,2-ethanedithiol with N-acylated indoles
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(Chemical Equation Presented) While attempting to prepare 2,5-dithiacyclopentyl derivatives from N-acyl 5-fluoroindole by reaction with 1,2-ethanedithiol we discovered that, instead of the expected product, annelation occurred to give a tricyclic compound containing a 3,6-dithiaazepine ring. This reaction is stereoselective and was found to be general for N-acylindoles, not being affected by substituents on the indole ring.
- Tsotinis, Andrew,Eleutheriades, Andreas,Di Bari, Lorenzo,Pescitelli, Gennaro
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- Trifluoromethylselenolation andN-acylation of indoles with [Me4N][SeCF3]
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An efficient method for oxidative trifluoromethylselenolation/N-acylation of indoles with excess [Me4N][SeCF3] in the presence of acyl peroxides and their derivatives is described. The reaction is easy to handle, proceeds smoothly at room temperature under metal-free conditions, and shows advantages such as good functional group tolerance, excellent regioselectivity, and compatibility of a number of substrates, producing 1-acyl and 3-trifluoromethylselanyl substituted indoles in good yields. Acyl peroxides and peroxycarboxylic acid behave as both oxidants and acyl sources in the transformation. This one-pot procedure provides a convenient access to a new class of indole derivatives, representing the first trifluoromethylselanyl bifunctionalization of indoles with the nucleophilic [Me4N][SeCF3] reagent.
- Dong, Tao,Tan, Kai-Li,Wang, Hao-Nan,Zhang, Cheng-Pan
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- Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage
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A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.
- Ye, Lu,Cai, Sai-Hu,Wang, Ding-Xing,Wang, Yi-Qiu,Lai, Lin-Jie,Feng, Chao,Loh, Teck-Peng
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- Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
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Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
- Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
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supporting information
p. 58 - 63
(2021/12/27)
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- Scaffold hopping by net photochemical carbon deletion of azaarenes
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Discovery chemists routinely identify purpose-tailored molecules through an iterative structural optimization approach, but the preparation of each successive candidate in a compound series can rarely be conducted in a manner matching their thought process. This is because many of the necessary chemical transformations required to modify compound cores in a straightforward fashion are not applicable in complex contexts. We report a method that addresses one facet of this problem by allowing chemists to hop directly between chemically distinct heteroaromatic scaffolds. Specifically, we show that selective photolysis of quinoline N-oxides with 390-nanometer light followed by acid-promoted rearrangement affords N-acylindoles while showing broad compatibility with medicinally relevant functionality. Applications to late-stage skeletal modification of compounds of pharmaceutical interest and more complex transformations involving serial single-atom changes are demonstrated.
- Woo, Jisoo,Christian, Alec H.,Burgess, Samantha A.,Jiang, Yuan,Mansoor, Umar Faruk,Levin, Mark D.
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p. 527 - 532
(2022/05/10)
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- N-2-pyrimidyl-3-fluoroindole compound and preparation method and application thereof
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The preparation method of the N-2-pyrimidinyl-3-fluoroindole compound shown in the formula (I) comprises the following steps: by taking an acetonitrile solvent as a reaction medium, adding the N-2-pyrimidinyl indole compound shown in the formula (III), se
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Paragraph 0066; 0070
(2021/03/31)
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- Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation
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We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides that is catalyzed by organophosphanes in the presence of base. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under
- Jeng, Wey-Chyng,Chien, Po-Chung,Vagh, Sandip Sambhaji,Edukondalu, Athukuri,Lin, Wenwei
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p. 4409 - 4418
(2021/08/25)
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- Direct photo-induced reductive Heck cyclization of indoles for the efficient preparation of polycyclic indolinyl compounds
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The photo-induced cleavage of C(sp2)-Cl bonds is an appealing synthetic tool in organic synthesis, but usually requires the use of high UV light, photocatalysts and/or photosensitizers. Herein is described a direct photo-induced chloroarene activation with UVA/blue LEDs that can be used in the reductive Heck cyclization of indoles and without the use of a photocatalyst or photosensitizer. The indole compounds examined display room-temperature phosphorescence. The photochemical reaction tolerates a panel of functional groups including esters, alcohols, amides, cyano and alkenes (27 examples, 50-88% yields), and can be used to prepare polycyclic compounds and perform the functionalization of natural product analogues in moderate to good yields. Mechanistic experiments, including time-resolved absorption spectroscopy, are supportive of photo-induced electron transfer between the indole substrate and DIPEA, with the formation of radical intermediates in the photo-induced dearomatization reaction.
- Che, Chi-Ming,Ling, Jesse,Liu, Yungen,To, Wai-Pong,Wu, Liang-Liang,You, Tingjie,Yu, Daohong
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p. 14050 - 14058
(2021/11/12)
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- A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
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A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
- Huang, Binbin,Guo, Lin,Xia, Wujiong
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supporting information
p. 2095 - 2103
(2021/03/26)
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- Direct oxidative coupling of: N -acyl pyrroles with alkenes by ruthenium(ii)-catalyzed regioselective C2-alkenylation
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Ruthenium(ii)-catalyzed oxidative coupling by C2-alkenylation of N-acyl pyrroles with alkenes has been described. The acyl unit was found to be an effective chelating group for the activation of aryl C-H bonds ortho to the directing group. The alkenylation reaction of benzoyl pyrroles occurred regioselectively at the C2-position of the pyrrole ring, without touching the benzene ring. The reaction provides exclusively monosubstituted pyrroles under the optimized conditions. Disubstituted pyrroles could be obtained using higher loadings of the ruthenium(ii)-catalyst and the additives.
- Chen, Weiqiang,Li, Hui-Jing,Li, Qin-Ying,Wu, Yan-Chao
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supporting information
p. 500 - 513
(2020/01/30)
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- N-Acylcarbazoles and N-Acylindoles: Electronically Activated Amides for N-C(O) Cross-Coupling by Nlpto Ar Conjugation Switch
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The development of new amide precursors for selective, catalytic activation of carbon-nitrogen bonds in amides is a fundamental objective of this emerging reactivity manifold. We report the palladium-catalyzed Suzuki-Miyaura cross-coupling of N-acylcarbazoles and N-acylindoles with arylboronic acids by a highly selective N-C(O) cleavage. The key amide bond ground-state destabilization stems from Nlp to Ar conjugation and enables us for the first time to achieve reactivity similar to that for N-acylsulfonamide and N-acylcarbamate activation in simple anilides.
- Buchspies, Jonathan,Rahman, Md. Mahbubur,Szostak, Roman,Szostak, Michal
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supporting information
p. 4703 - 4709
(2020/06/17)
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- Palladium-Catalyzed Desulfurative Amide Formation from Thioureas and Arylboronic Acids
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The development of the reactivity on carbene complexes would lead to the creation of novel synthetic strategies. We discovered herein the Pd-catalyzed desulfurative amide formation involved Suzuki-Miyaura coupling reaction, notably the Pd complex was generated in situ from thioureas, Ag salt and Pd catalyst. Silver salt was essential for the construction of this type of carbenes from available and stable thioureas and well participated in the catalytic cycle. We report a method for the synthesis of arylamides from arylboronic acids, which greatly enriched the application of thiourea chemistry and expanded the application of the Suzuki-Miyaura coupling.
- Su, Jianke,Li, Wendong,Li, Xin,Xu, Jian,Song, Qiuling
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p. 5664 - 5668
(2020/10/02)
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- Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3
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Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.
- Iqbal, Saqib A.,Cid, Jessica,Procter, Richard J.,Uzelac, Marina,Yuan, Kang,Ingleson, Michael J.
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supporting information
p. 15381 - 15385
(2019/10/22)
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- Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation
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A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.
- Sitte, Nikolai A.,Bursch, Markus,Grimme, Stefan,Paradies, Jan
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supporting information
p. 159 - 162
(2019/01/04)
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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 0059; 0076; 0077
(2018/10/02)
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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 0050-0052
(2018/12/02)
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- Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles
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A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.
- Xia, Hai-Dong,Zhang, Yan-Dong,Wang, Yan-Hui,Zhang, Chi
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p. 4052 - 4056
(2018/07/15)
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- CuCl2/[hmim]Br: A new recyclable catalytic system for aromatization of cyclic dienes
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The combination of copper(II) chloride and 1-hexyl-3-methylimidazolium bromide ([hmim]Br) as a new recyclable catalytic system in the presence of TBHP for aromatization of cyclic dienes is disclosed. The system could furnish the corresponding aromatics in moderate to excellent yield. The competition between aromatization and oxidation of benzylic substrates were also studied. This developed catalytic system could be reused and recycled at least nine times without significant loss of the producitivity.
- Taboonpong, Piyada,Chavasiri, Warinthorn
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- C3-Selective alkenylation of N-acylindoles with unactivated internal alkynes by cooperative nickel/aluminium catalysis
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Highly regio- and stereoselective alkenylation of N-acylindoles with unactivated internal alkynes has been accomplished by cooperative nickel/aluminium catalysis to afford C3-alkenylated indoles. Coordination of the acyl moiety to a bulky aluminium-based Lewis acid plays a crucial role in the selective functionalization at the C3-position by electron-rich nickel(0) catalysis.
- Inoue, Fumiyoshi,Saito, Teruhiko,Semba, Kazuhiko,Nakao, Yoshiaki
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supporting information
p. 4497 - 4500
(2017/04/26)
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- Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides
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Selective C-H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl2. Interestingly, analogous reactions in the absence of ZnCl2 resulted in the formation of indole aminal products.
- Ortiz, Gerardo X.,Hemric, Brett N.,Wang, Qiu
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p. 1314 - 1317
(2017/03/23)
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- Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2O
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A novel condensation reaction of carboxylic acids with various non-nucleophilic N-heterocycles and anilides was developed. The reaction proceeds in the presence of di-tert-butyl dicarbonate (Boc2O), catalytic 4-(dimethylamino)pyridine (DMAP), a
- Umehara, Atsushi,Ueda, Hirofumi,Tokuyama, Hidetoshi
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p. 11444 - 11453
(2016/11/28)
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- A Direct Access to 7-Aminoindoles via Iridium-Catalyzed Mild C-H Amidation of N-Pivaloylindoles with Organic Azides
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Ir(III)-catalyzed regioselective direct C-7 amidation of indoles in reaction with organic azides has been developed. While its efficiency was varied by the choice of N-directing groups, N-pivaloylindoles were most effective in undergoing the desired amidation at room temperature over a broad range of substrates. The reaction was scalable, and deprotection of the chelation group was also facile.
- Kim, Youyoung,Park, Juhyeon,Chang, Sukbok
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supporting information
p. 1892 - 1895
(2016/05/19)
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- An efficient and green method for regio- and chemo-selective Friedel-Crafts acylations using a deep eutectic solvent ([CholineCl][ZnCl2]3)
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[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel-Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.
- Tran, Phuong Hoang,Nguyen, Hai Truong,Hansen, Poul Erik,Le, Thach Ngoc
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p. 37031 - 37038
(2016/05/24)
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- Preparation of magnetically recyclable MIL-53(Al)@SiO2@Fe3O4 catalysts and their catalytic performance for Friedel-Crafts acylation reaction
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Novel magnetically recyclable MIL-53(Al)@SiO2@Fe3O4 catalysts with different MIL-53(Al) contents were prepared by encapsulating magnetic SiO2@Fe3O4 nanoparticles into MIL-53(Al) through an in situ method. The structure of the catalysts was characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR) spectroscopy, vibration sample magnetometer (VSM), and N2 adsorption/desorption techniques. Catalytic activity and recovery properties of the catalysts for Friedel-Crafts acylation reaction of 2-methylindole with benzoyl chloride were evaluated. The results showed that the magnetic MIL-53(Al)@SiO2@Fe3O4 catalysts have the larger surface areas, suitable superparamagnetism, and good catalytic activity for Friedel-Crafts acylation reaction. Over 38.8% MIL-53(Al)@SiO2@Fe3O4 catalyst under the reaction conditions of 25 °C for 8 h the conversion of 2-methylindole can reach ~98%, and the selectivity of 3-acetylindole and that of N-acetylindole can reach ~81% and ~18%, respectively. After the reaction, the catalyst can be easily separated from the reactant mixture by an external magnet. The recovered catalyst can be reused for five times, and the conversion of 2-methylindole can be kept over 90% and the selectivity of 3-acetylindole can be maintained at 80%.
- Jiang, Sai,Yan, Junlei,Habimana, Fabien,Ji, Shengfu
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- Palladium-Catalyzed Carbonylative Synthesis of N -Benzoylindoles with Mo(CO)6 as the Carbon Monoxide Source
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A mild and carbon monoxide gas-free palladium-catalyzed aminocarbonylation of indole has been developed for the synthesis of N-benzoylindoles. This method uses Mo(CO)6 as a convenient CO-precursor and BuPAd2 as the ligand. A number o
- Wu, Xiao-Feng,Oschatz, Stefan,Sharif, Muhammad,Langer, Peter
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p. 2641 - 2646
(2015/09/01)
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- Site-Selective Addition of Maleimide to Indole at the C-2 Position: Ru(II)-Catalyzed C-H Activation
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Synthesis of 3-(indol-2-yl)succinimide derivatives is presented using a directing group strategy. Selective functionalization of C-2 in the presence of highly reactive C-3 in indole derivatives has been achieved. A conjugate addition product instead of He
- Lanke, Veeranjaneyulu,Bettadapur, Kiran R.,Prabhu, Kandikere Ramaiah
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supporting information
p. 4662 - 4665
(2015/10/12)
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- Metal-organic framework MIL-53(Al): Synthesis, catalytic performance for the Friedel-Crafts acylation, and reaction mechanism
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Metal-organic framework MIL-53(Al) was synthesized by a solvothermal method using aluminum nitrate as the aluminium source and 1,4-benzenedicarboxylic acid (H2BDC) as the organic ligand. The structure of samples was characterized by X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FT-IR). The catalytic activity and recyclability of MIL-53(Al) catalyst for the Friedel-Crafts acylation reaction of indole with benzoyl chloride were evaluated. The reaction conditions were optimized and a reaction mechanism was suggested. The results showed that the MIL-53(Al) catalyst exhibited good catalytic activity and recyclability for the Friedel-Crafts acylation reaction. When the molar ratio of indole and MIL-53(Al) catalyst was 1:0.06 (n 1:n catalyst), the molar ratio of indole and benzoyl chloride was 1:3, and the solvent was dichloromethane, the conversion of indole could reach 97.1% and the selectivity of 3-acylindole could reach 81.1% at 25 °C after 8 h. The catalyst can be reused without significant degradation in catalytic activity. After the catalyst was reused five times, the conversion of indole was 87.6% and the selectivity of 3-acylindole was 79.5%.
- Yan, Junlei,Jiang, Sai,Ji, Shengfu,Shi, Da,Cheng, Hefei
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p. 1544 - 1552
(2015/10/06)
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- Palladium-catalyzed intermolecular C-2 alkenylation of indoles using oxygen as the oxidant
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A general and efficient palladium-catalyzed intermolecular direct C-2 alkenylation of indoles using oxygen as the oxidant has been developed. The reaction is of complete regio- and stereoselectivity. All products are E-isomers at the C-2-position with no Z-isomers and 3-substituted products were detected.
- Yan, Zhao-Lei,Chen, Wen-Liang,Gao, Ya-Ru,Mao, Shuai,Zhang, Yan-Lei,Wang, Yong-Qiang
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supporting information
p. 1085 - 1092
(2014/04/03)
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- Heterolysis of NH-indoles by bifunctional amido complexes and applications to carboxylation with carbon dioxide
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Bifunctional amidoiridium complexes bearing C-N chelate ligands readily deprotonate unprotected NH-indole to give new κ1-N-indolyl(amine) complexes, quantitatively. The resulting complexes were fully characterized by NMR, elemental analysis, and X-ray crystallography. The analogous Rh and Ru complexes were also synthesized by treatment of the precursory amine complexes with free indole in the presence of an equimolar amount of KOtBu. The indolyl moiety bound to the Ir center exhibits nucleophilic character to react with benzoyl chloride and to give 1- and 3-acylated indoles in yields of 68% and 18%, respectively. A related amido-Ru complex derived from an N-sulfonylated 1,2-diphenylethylenediamine ligand promoted carboxylation of indoles with CO2 under basic conditions to give indole-1-carboxylic acids.
- Ueno, Atsushi,Kayaki, Yoshihito,Ikariya, Takao
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supporting information
p. 4479 - 4485
(2015/04/16)
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- Indole synthesis based on a modified koser reagent
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A new metal-free method for the rapid and productive preparation of indoles has been developed. This process is based on sterically congested hypervalent iodine compounds of the family of Koser reagents, and iodosobenzene in combination with 2,4,5-tris-isopropylbenzene sulfonic acid provides the highest yields and fastest reaction times. This reagent alone promotes the chemoselective oxidative cyclization of 2-amino styrenes to indoles in high yields under mild conditions. Convenient route to indole: A fast, productive, and operationally simple indole synthesis was developed.
- Fra, Laura,Millán, Alba,Souto, José A.,Mu?iz, Kilian
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p. 7349 - 7353
(2014/07/21)
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- Highly regioselective C2-alkenylation of indoles Uusing the N-benzoyl directing group: An efficient Ru-catalyzed coupling reaction
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A highly regioselective alkenylation of indole at the C2-position has been achieved using the Ru(II) catalyst by employing a directing group strategy. This strategy offers rare selectivity for the alkenylation N-benzoylindole at the C-2 position in the pr
- Lanke, Veeranjaneyulu,Prabhu, Kandikere Ramaiah
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supporting information
p. 2818 - 2821
(2013/07/19)
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- A novel microwave-irradiated solvent-free 3-acylation of indoles on alumina
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A simple and efficient 3-acylation of indoles under microwave-heated and solvent-free conditions is developed. This general procedure uses neutral Al2O3 as a new, green and reusable catalyst giving good to high yields within short reaction times. Utilizing such an environmentally- benign methodology, a variety of indoles bearing electron-releasing or electron-withdrawing groups were conveniently acylated.
- Lai, Qiu Yu,Liao, Rong Su,Wu, Shao Yong,Zhang, Jia Xin,Duan, Xin Hong
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p. 4069 - 4076
(2013/12/04)
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- Synthesis of highly N-substituted indole library via conjugate additions of indoline and their synthetic tool potentials
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A comprehensive library of N- or 1-substituted indoles was formed by conjugate additions of indoline with Michael acceptors followed by an oxidation step. Using N-substituted indoles as key Michael donors, the synthesis of 1,3-disubstituted indoles was al
- Kilic, Haydar,Bayindir, Sinan,Erdogan, Esra,Saracoglu, Nurullah
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p. 5619 - 5630
(2012/09/08)
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- Ir(I)-catalyzed C-H bond alkylation of C2-position of indole with alkenes: Selective synthesis of linear or branched 2-alkylindoles
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A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.
- Pan, Shiguang,Ryu, Naoto,Shibata, Takanori
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supporting information
p. 17474 - 17477,4
(2012/12/12)
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- Ir(I)-catalyzed C-H bond alkylation of C2-position of indole with alkenes: Selective synthesis of linear or branched 2-alkylindoles
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A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.
- Pan, Shiguang,Ryu, Naoto,Shibata, Takanori
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supporting information
p. 17474 - 17477
(2013/01/15)
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- Cesium carbonate-promoted hydroamidation of alkynes: Enamides, indoles and the effect of iron(III) chloride
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A series of enamide derivatives was prepared by a simple procedure for the hydroamidation of alkynes with amides and sulfonamides. The use of such a mild base as cesium carbonate promotes the latter transformation, and the addition of catalytic amounts of iron(III) chloride has a beneficial effect in the outcome of some of the presented hydroamidation reactions. A range of indoles was also synthesized from ortho-alkynylanilides by both complementary procedures, which proved to be useful for the construction of the indolo[1,2-c]quinazoline tetracyclic system from an ortho-(2-aminophenylalkynyl)anilide. Copyright
- Herrero, Maria Teresa,De Sarralde, Jokin Diaz,Sanmartin, Raul,Bravo, Laura,Dominguez, Esther
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p. 3054 - 3064
(2013/01/15)
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- Chemoselective N-acylation of indoles and oxazolidinones with carbonylazoles
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Unique reactivity: In the presence of more reactive amine and alcohol functional groups and of carboxylic acids, the chemoselective N-acylation of indoles (see scheme) and oxazolidinones is achieved by taking advantage of the unique reactivity of carbonylazole acylating agents with catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Copyright
- Heller, Stephen T.,Schultz, Erica E.,Sarpong, Richmond
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supporting information; experimental part
p. 8304 - 8308
(2012/09/08)
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- Synthesis of 6H-isoindolo[2,1-a]indol-6-ones through a sequential copper-catalyzed C-N coupling and palladium-catalyzed C-H activation reaction
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A series of 6H-isoindolo[2,1-a]indol-6-ones were synthesized through one-pot sequential coupling reactions, which were comprised of a copper-catalyzed C-N coupling cyclization and a palladium-catalyzed C-H activation course. General chemicals benzoyl chlorides and o-gem-dibromovinyl anilines were employed as the starting substrates.
- He, Hua-Feng,Dong, Sheng,Chen, Yi,Yang, Yang,Le, Yueqin,Bao, Weiliang
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p. 3112 - 3116
(2012/06/01)
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- Thermally decomposed Ni-Fe-hydrotalcite: A highly active catalyst for the solvent-free N-acylation of different amines by acid chlorides
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A composite Ni-Fe catalyst obtained from the thermal decomposition of Ni-Fe-hydrotalcite at 600 °C shows very high activity in the solvent-free N-acylation of amines by different acid chlorides with high product yields under very mild reaction conditions (viz. room temperature, short reaction period and small amount of catalyst). The catalyst also shows excellent reusability in the reaction. The crystalline phases present in the catalyst are mixed oxides and hydroxides of nickel and iron. The high catalytic activity of the decomposed Ni-Fe-hydrotalcite is attributed to the formation of uniformly distributed Ni-Fe metal oxides and hydroxides.
- Choudhary,Dumbre
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experimental part
p. 1351 - 1356
(2012/01/06)
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- NOVEL INDOLIC DERIVATIVES, THEIR PREPARATION PROCESSES AND THEIR USES IN PARTICULAR AS ANTIBACTERIALS
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The invention relates to the use of at least one compound of the formula (I), in which R and R3 are particularly a hydrogen atom, R1 is particularly a hydrogen atom or a methyl, ethyl or isobutyl mi group, R4, R5, R6 and R7 are independently a hydrogen atony, an alkoxyl group with 1 to 7 carbon atoms or a halogen atom, R2 is a hydrogen atom, an O? group or an OH group, B is an N-GP1 or NRc, group, GP1 being a Boc or Cbz group, and Rc is a hydrogen atom or a methyl or t-butyl group, for preparing a drug for treating conditions associated with bacterial infections, in particular for treating bacterial diseases.
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Page/Page column 46
(2010/06/19)
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- Mo(CO)6-mediated carbamoylation of aryl halides
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A simple method for the synthesis of amides has been developed by molybdenum-mediated carbamoylation of aryl halides. Whereas the conventional palladium-catalyzed three-component coupling reaction requires a large excess of gaseous carbon monoxide, the incorporation of carbon monoxide in this Mo-mediated carbamoylation reaction is so efficient that it requires only a slight excess amount of carbon monoxide in the form of its molybdenum complex, Mo(CO)6. The reaction is applicable for the synthesis of a wide variety of not only secondary and tertiary amides but also primary amides by using aqueous ammonia.
- Ren, Wei,Yamane, Motoki
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experimental part
p. 8410 - 8415
(2011/02/23)
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- Mild and useful method for n-acylation of amines
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Iodine is found to promote quantitative N-acylation of primary and secondary amines (aliphatic and aromatic) in a very short time with an equimolar amount of acetyl chloride and benzoyl chloride under solvent-free conditions at room temperature. This catalytic acylation of amines offers an additional useful method for the acetylation using acetyl chloride instead of acetic anhydride and other acetylating agents. This method is also useful in the N-acylation of heterocycles. Mild reaction condition, high selectivity, efficiency, and good yields are some of the major advantages of the procedure.
- Phukan, Kandarpa,Ganguly, Mausumi,Devi, Nirada
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experimental part
p. 2694 - 2701
(2009/12/06)
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- A novel one-pot synthesis of N-acylindoles from primary aromatic amides
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A novel one-pot synthesis of N-acylindoles via tandem cycloalkylation- annelation is described. This approach is based on the use of a strong solid-acid catalyst, montmorillonite K-10, and microwave irradiation under solvent-free conditions. The tandem cy
- Abid, Mohammed,De Paolis, Omar,T?r?k, Béla
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p. 410 - 412
(2008/09/17)
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- Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air: Reaction development and scope
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(Figure Presented) New reaction conditions for intramolecular palladium(II)-catalyzed oxidative carbon-carbon bond formation under air are described. The use of pivalic acid as the reaction solvent, instead of acetic acid, results in greater reproducibility, higher yields, and broader scope. This includes the use of electron-rich diarylamines as illustrated in the synthesis of three naturally occurring carbazole products: Murrayafoline A, Mukonine, and Clausenine. A variety of side products have also been isolated, casting light on competing reaction pathways and revealing new reactivity with palladium(II) catalysis.
- Liegault, Benoit,Lee, Doris,Huestis, Malcolm P.,Stuart, David R.,Fagnou, Keith
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p. 5022 - 5028
(2008/09/21)
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- C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls
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The aerobic oxidative coupling of arenes such as benzofuran and N-substituted indoles with benzene and derivatives thereof is described. The reaction is shown to take place in both inter- and intramolecular scenarios.
- Dwight, Timothy A.,Rue, Nicholas R.,Charyk, Dagmara,Josselyn, Ryan,DeBoef, Brenton
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p. 3137 - 3139
(2008/02/10)
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