- Heteroaryl radicals in synthesis: Radical cyclisation reactions of 2-bromoindoles
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The synthesis and radical cyclisations of 2-bromoindoles carrying an unsaturated N-alkyl group is described.
- Dobbs, Adrian P.,Jones, Keith,Veal, Ken T.
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Read Online
- Syntheses of polybrominated indoles from the red alga Laurencia brongniartii and the brittle star Ophiocoma erinaceus
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The red alga Laurencia brongniartii and brittle star Ophiocoma erinaceus metabolites 2,3,6-tribromo-1-methylindole (1) and 2,3,5,6-tetrabromo-1-methylindole (2) are easily synthesized selectively from 2,3-dibromo-1-methylindole (5), which in turn is prepared from indole (3) in one continuous sequence in 92% yield. Moreover, 2 can be made from both 1 and 5 in 67% and 65% yields, respectively.
- Liu, Yanbing,Gribble, Gordon W.
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Read Online
- Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics
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We presented a palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins, which utilize H-phosphinates and secondary phosphine oxides as the phosphine sources, respectively. A variety of phosphorylated heteroaromatics were obtained in m
- Chen, Chen,Ding, Jie,Liu, Liying,Huang, Yujie,Zhu, Bolin
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p. 200 - 205
(2021/10/29)
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- Method for preparing 2-bromoindole by using electrochemical micro-channel device
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The invention provides a method for preparing 2-bromoindole by using an electrochemical micro-channel device, which comprises the following steps: assembling an electrochemical micro-channel reactiondevice, and dissolving indole compounds and bromine-cont
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Paragraph 0021-0053
(2021/01/24)
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- Palladium-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines
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An efficient Pd(0)-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines is reported. Few methods have aimed to synthesize these scaffolds which are found in many natural products and have high bioactivity. This protocol features a robust c
- Zeidan, Nicolas,Bognar, Sabine,Lee, Sophia,Lautens, Mark
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supporting information
p. 5058 - 5061
(2017/11/07)
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- Selective access to 3-cyano-1 H -indoles, 9 H -pyrimido[4,5- b ]indoles, or 9 H -Pyrido[2,3- b ]indoles through copper-catalyzed one-pot multicomponent cascade reactions
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Novel and selective synthetic approaches toward indole derivatives via copper-catalyzed one-pot multicomponent cascade reactions of 1-bromo-2-(2,2-dibromovinyl)benzenes with aldehydes and aqueous ammonia are presented. Intriguingly, the concentration of a
- Li, Bin,Guo, Shenghai,Zhang, Ju,Zhang, Xinying,Fan, Xuesen
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p. 5444 - 5456
(2015/06/16)
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- Application of nanoparticle mediated N-arylation of amines for the synthesis of pharmaceutical entities using vit-E analogues as amphiphiles in water
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The first CuI-nanoparticle catalyzed inter and intramolecular N-arylation of amines using vitamin E analogues (TPGS) as amphipiles has been developed in water. Application of this transition metal-amphiphile C-N bond formation methodology is further extended for the synthesis of substituted indoles, bioactive natural product tryptanthrin and intermediates of pharmaceutical entities such as imatinib, nilotinib, selective D3 agonist/antagonist ligands, and oxacarbazepine. This journal is
- Kumar, Atul,Bishnoi, Ajay Kumar
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p. 20516 - 20520
(2015/03/30)
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- Microwave irradiated synthesis of 2-bromo(chloro)indoles via intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in the presence of TBAF under metal-free conditions
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2-Bromo(chloro)indoles were readily and efficiently prepared through TBAF-promoted intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in excellent yields under metal-free and microwave irradiation conditions. This journal is the Partner Organisations 2014.
- Wang, Min,Li, Pinhua,Chen, Wei,Wang, Lei
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p. 26918 - 26923
(2014/07/21)
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- Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid
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An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.
- Miyamoto, Hiroshi,Hirano, Tomohiro,Okawa, Yoichiro,Nakazaki, Atsuo,Kobayashi, Susumu
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supporting information
p. 9481 - 9493
(2013/10/08)
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- The facile synthesis of 2-bromoindoles via Cs2CO 3-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions
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2-Bromoindoles were readily prepared through a facile Cs2CO 3-promoted intramolecular cyclization of 2-(gem-bromovinyl)-N- methylsulfonylanilines in excellent yields under transition-metal-free conditions. This methodology could be extended to the synthesis of corresponding 2-chloroindoles. The reaction mechanism suggested that cyclization occurs through a key intermediate, phenylethynyl bromide, followed by cyclization in one-pot. The Royal Society of Chemistry.
- Li, Pinhua,Ji, Yong,Chen, Wei,Zhang, Xiuli,Wang, Lei
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- An efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl)indoles via tandem reactions of 2-(gem-dibromo(chloro)vinyl)anilines with diselenides(disulfides)
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A novel and efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl) indoles through tandem reactions of 2-(gem-dibromo(chloro)vinyl)-N- methylsulfonylanilines with diselenides and disulfides in the presence of t-BuOLi and I2 (10 mol%) in DMS
- Liu, Jie,Li, Pinhua,Chen, Wei,Wang, Lei
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p. 10052 - 10054
(2012/10/30)
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- Copper-catalyzed domino intramolecular cyclization: A facile and efficient approach to polycyclic indole derivatives
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A mild and efficient Cu2O-catalyzed domino intramolecular C-N coupling/C-Y (Y = O, S, N) bond formation was successfully achieved. Thus oxazino[3,2-a]indole, thiazino[3,2-a]indole and indolo[2,1-b]quinazoline derivatives were facilely assembled
- Xia, Ziming,Wang, Kuo,Zheng, Jiening,Ma, Zheyong,Jiang, Zhanguo,Wang, Xiaoxia,Lv, Xin
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experimental part
p. 1602 - 1611
(2012/03/22)
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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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- The role of reversible oxidative addition in selective palladium(0)- catalyzed intramolecular cross-couplings of polyhalogenated substrates: Synthesis of brominated indoles
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A Pd(0)-catalyzed C-N bond-forming reaction leading to the synthesis of brominated indoles is described. The use of the phosphine ligand PtBu 3 is necessary for reactivity. It is proposed that the bulky ligand serves to prevent inhibition of th
- Newman, Stephen G.,Lautens, Mark
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supporting information; experimental part
p. 11416 - 11417
(2010/10/01)
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- Intramolecular cross-coupling of gem-dibromoolefins: A mild approach to 2-bromo benzofused heterocycles
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Highly useful halogenated benzofurans and benzothiophenes are prepared from readily available gem-dibromoolefins using a mild, ligand-free copper catalyzed cross-coupling procedure.
- Newman, Stephen G.,Aureggi, Valentina,Bryan, Christopher S.,Lautens, Mark
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supporting information; experimental part
p. 5236 - 5238
(2010/01/31)
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- A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles
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(Chemical Equation Presented) A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline leading to indoles with group at C2-C7. The orthogonal approach of the sequential copper- and palladium-mediated synthesis of 1,2-diarylindoles exploited the wide availability of diverse organoboron reagents.
- Fang, Yuan-Qing,Lautens, Mark
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p. 538 - 549
(2008/09/17)
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- Hypoglycemic imidazoline compounds
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This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation.
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- Generation and reactivity of 1,2-dilithioindole
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The generation of a 1,2-dianion (1) from 2-iodoindole is described. This dianion reacts at the carbanionic center with a range of electrophiles to give 2-substituted indoles in good yields.
- Herbert, John M.,Maggiani, Maria
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p. 947 - 951
(2007/10/03)
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- Annulation of indole via indole radicals: Addition of the 2-indolyl radical to aromatic rings
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The reactions of the radicals derived from indoles 4 are described leading to a short synthesis of fused [1,2-a]indoles via radical addition to the benzene ring followed by rearomatisation whilst one example undergoes an unusual radical translocation/addition reaction. (C) 2000 Elsevier Science Ltd.
- Fiumana, Andrea,Jones, Keith
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p. 4209 - 4211
(2007/10/03)
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- Intermolecular reactions of indol-2-yl radicals: A new route to 2-substituted indoles
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The generation of indol-2yl radicals and their addition to a variety of radical accepters to prepare 2-substituted indoles is presented.
- Fiumana, Andrea,Jones, Keith
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p. 1761 - 1762
(2007/10/03)
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- THE PREPARATION AND SPECTRAL CHARACTERIZATION OF 2-HALOINDOLES, 3-HALOINDOLES, AND 2,3-DIHALOINDOLES
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The preparation and properties of a series of 2- and 3-haloindoles and 2,3-dihaloindoles are described, and the mechanism of halogenation of 3-halo substituted indoles is briefly discussed.
- Brennan, Mary R.,Erickson, Karen L.,Szmalc, Frank S.,Tansey, Marilyn J.,Thornton, Janice M.
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p. 2879 - 2885
(2007/10/02)
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