- Construction of the Pyrrolo[2,3- d]carbazole Core of Spiroindoline Alkaloids by Gold-Catalyzed Cascade Cyclization of Ynamide
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We achieved direct construction of the common pyrrolo[2,3-d]carbazole core of aspidosperma and malagasy alkaloids by a gold-catalyzed cascade cyclization of ynamide. This reaction involves intramolecular cyclization from indole to ynamide followed by trapping of the resulting iminium intermediate. Through the use of chiral gold complexes, an enantiomerically enriched pyrrolo[2,3-d]carbazole was obtained in up to 74% ee. This methodology was successfully applied to the asymmetric formal synthesis of vindorosine.
- Matsuoka, Junpei,Kumagai, Hiroshi,Inuki, Shinsuke,Oishi, Shinya,Ohno, Hiroaki
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- Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
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Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.
- Chang, Sukbok,Kim, Dongwook,Kim, Youyoung
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supporting information
p. 12309 - 12312
(2021/12/07)
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- Rhodium-Catalyzed Stereoselective Cyclization of 3-Allenylindoles and N-Allenyltryptamines to Functionalized Vinylic Spiroindolenines
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Herein, we report a highly enantio- and diastereoselective rhodium-catalyzed cyclization of N-allenyltryptamines and 3-allenylindoles to 6-membered spirocyclic indolenines. This allylic addition methodology offers the advantage of using a comparably cheap commercially available ligand with low loadings of an affordable rhodium precursor. The products can be converted into functionalized spirooxindoles and spiroindolines, which are regarded as important building blocks for the synthesis of a lot of natural products with biological activities.
- Becker, Antonia,Breit, Bernhard,Grugel, Christian P.
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supporting information
p. 3788 - 3792
(2021/05/29)
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- Preparation method of azepano[4,5-b]indole compound
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The invention discloses a preparation method of an azepano[4,5-b]indole compound, which comprises the following steps: by taking tryptamine or a derivative thereof as an initial raw material, protecting an NH2 group of a side chain alkyl group, protecting
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Paragraph 0051-0053
(2021/07/17)
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- Evaluation and docking of indole sulfonamide as a potent inhibitor of α-glucosidase enzyme in streptozotocin –induced diabetic albino wistar rats
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We have synthesized new hybrid class of indole bearing sulfonamide scaffolds (1–17) as α-glucosidase inhibitors. All scaffolds were found to be active except scaffold 17 and exhibited IC50 values ranging from 1.60 to 51.20 μM in comparison with
- Taha, Muhammad,Imran, Syahrul,Salahuddin, Mohammed,Iqbal, Naveed,Rahim, Fazal,Uddin, Nizam,Shehzad, Adeeb,Khalid Farooq, Rai,Alomari, Munther,Mohammed Khan, Khalid
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- Replacing halogenated solvents by a butyl acetate solution of bisphenol S in the transformations of indoles
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A butyl acetate solution of bisphenol S (BPS) was proved to be able to replace hazardous halogenated solvents in the transformation of indoles. Measurement with Kamlet-Taft solvatochromic parameters disclosed that the polarity of the BPS-containing butyl acetate was enhanced greatly. The protocol not only conferred a convenient way to minimize the use of halogenated solvents in the synthesis of indole derivatives, but also enabled successful recycling of both the butyl acetate solvent and BPS additive, strengthening the greenness of the reaction systems.
- Bai, Rongxian,Ferlin, Francesco,Gao, Feng,Gu, Yanlong,Li, Minghao,Vaccaro, Luigi
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supporting information
p. 3588 - 3594
(2021/06/06)
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- Synthesis of CF3-Containing Spirocyclic Indolines via a Red-Light-Mediated Trifluoromethylation/Dearomatization Cascade
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A red-light-mediated nPr-DMQA+-catalyzed cascade intramolecular trifluoromethylation and dearomatization of indole derivatives with Umemoto's reagent has been developed. This protocol provides a facile and efficient approach for the construction of functionalized and potentially biologically important CF3-containing 3,3-spirocyclic indolines with moderate to high yields and excellent diastereoselectivities under mild conditions. The success of multiple gram-scale (1 and 10 g) experiments further highlights the robustness and practicality of this protocol and the merit of the employment of red light. Mechanistic studies support the formation of a crucial CF3 radical species and a dearomatized benzyl carbocation intermediate.
- Gianetti, Thomas L.,Mei, Liangyong,Moutet, Jules,Stull, Savannah M.
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supporting information
p. 10640 - 10653
(2021/07/31)
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- Synthesis, biological evaluation, and docking study of indole aryl sulfonamides as aromatase inhibitors
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In order to identify new aromatase enzyme inhibitors, thirty aryl sulfonamide derivatives containing an indole nucleus have been synthesized. The enzyme inhibition assay showed that four compounds inhibit aromatase in the sub-micromolar range. Loading concentrations of these four compounds were afterwards tested for cell viability and cytotoxicity on MCF7 human breast cancer cells, revealing a time- and dose-dependent decrease of active metabolizing cells over the time of the culture (0–72 h), starting from a concentration of 100 μM. Likewise LDH released raised up to 40% at early time of exposures (24 h). Finally, the docking study showed that the best active compounds efficiently bound in the active site of the aromatase; high values of HBD and low levels of HBA are the principal requirement evidenced by the QSAR model.
- Fantacuzzi, Marialuigia,De Filippis, Barbara,Gallorini, Marialucia,Ammazzalorso, Alessandra,Giampietro, Letizia,Maccallini, Cristina,Aturki, Zeineb,Donati, Enrica,Ibrahim, Reham S.,Shawky, Eman,Cataldi, Amelia,Amoroso, Rosa
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- The Plasmodium falciparum eIK1 kinase (PfeIK1) is central for melatonin synchronization in the human malaria parasite. Melatotosil blocks melatonin action on parasite cell cycle
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Melatonin and its indoles derivatives are central in the synchronization of malaria parasites. In this research, we discovered that melatonin is unable to increase the parasitemia in the human malaria Plasmodium falciparum that lacks the kinase PfeIK1. Th
- Alves, Marina Rangel Rodrigues,Costa da Silva Almeida, Fahyme,Dias, Bárbara K. M.,Garcia, Celia R. S.,Jord?o, Alessandro Kappel,Nakabashi, Myna,Portella, Danielle Pagliaminuto,Ribeiro, Ramira Yuri,Schuck, Desiree C.,dos Santos, Benedito Matheus
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- Tricyclic indole derivative and preparation and application thereof
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The invention discloses a tricyclic indole derivative and a preparation method application thereof. The tricyclic indole derivative has the following structural formula which is as shown in the specification, wherein hydroxyl at the position of 3a is the
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Paragraph 0020; 0026-0028
(2020/02/07)
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- Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones
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A chiral phosphine-catalyzed tandem Michael addition of tryptamine-derived oxindoles to ynones has been developed, which provides facile access to a series of optically enriched spiro[pyrrolidine-3,3′-oxindole] compounds in good yields with good to excell
- Cong, Tiantian,Wang, Huamin,Li, Xiuzheng,Wu, Hai-Hong,Zhang, Junliang
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supporting information
p. 9176 - 9179
(2019/08/07)
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- Gold-Catalyzed Asymmetric Intramolecular Cyclization of N-Allenamides for the Synthesis of Chiral Tetrahydrocarbolines
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Highly enantioselective gold-catalyzed intramolecular cyclization of N-allenamides was implemented by utilizing a designed chiral sulfinamide phosphine ligand (PC-Phos). This represents the first example of highly enantioselective intramolecular cyclization of N-allenamides. The practicality of this reaction was validated in the total synthesis of (R)-desbromoarborescidine A and formal synthesis of (R)-desbromoarborescidine C and (R)-deplancheine. Moreover, the catalyst system PC-Phos/AuNTf2 proved to be specifically efficient to promote the desymmetrization of N-allenamides in excellent yields with satisfactory ee values.
- Wang, Yidong,Zhang, Peichao,Di, Xiaoyu,Dai, Qiang,Zhang, Zhan-Ming,Zhang, Junliang
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supporting information
p. 15905 - 15909
(2017/11/27)
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- Synthesis, molecular docking, and QSAR study of sulfonamide-based indoles as aromatase inhibitors
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Thirty four of indoles bearing sulfonamides (11–44) were synthesized and evaluated for their anti-aromatase activities. Interestingly, all indole derivatives inhibited the aromatase with IC50 range of 0.7–15.3 μM. Indoles (27–36) exerted higher aromatase inhibitory activity than that of ketoconazole. The phenoxy analogs 28 and 34 with methoxy group were shown to be the most potent compounds with sub-micromolar IC50 values (i.e., 0.7 and 0.8 μM, respectively) without affecting to the normal cell line. Molecular docking demonstrated that the indoles 28, 30 and 34 could occupy the same binding site on the aromatase pocket and share several binding residues with those of the natural substrate (androstenedione), which suggested the competitive binding could be the mode of inhibition of the compounds. The most potent analog 28 could mimic H-bond interactions of the natural androstenedione with MET374 and ASP309 residues on the aromatase. QSAR model also revealed that the para-phenoxy indole (28) affords the higher value of electronegativity descriptor MATS6e as well as the higher inhibitory activity compared with that of the ortho-phenoxy compound (34). The study highlighted a series of promising indoles to be potentially developed as novel aromatase inhibitors for therapeutics.
- Pingaew, Ratchanok,Mandi, Prasit,Prachayasittikul, Veda,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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p. 1604 - 1615
(2017/11/17)
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- Br?nsted Acid-Catalyzed Tandem Cyclizations of Tryptamine-Ynamides Yielding 1H-Pyrrolo[2,3-d]carbazole Derivatives
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Ynamides, as versatile synthetic precursors, have attracted much attention from synthetic chemists and sparked the development of a number of methodologies for the construction of various structures. 1H-Pyrrolo[2,3-d]carbazole is a core scaffold of a series of monoterpene indole alkaloids found in Kopsia, Strychnos, and Aspidosperma, for example. In this study, 1H-pyrrolo[2,3-d]carbazole derivatives were synthesized by a Br?nsted acid-catalyzed tandem cyclization starting from tryptamine-based ynamides. This strategy prevented Wagner–Meerwein rearrangement by instantaneous intramolecular nucleophilic trapping of the indoleninium to afford a tetracyclic indoline via an in situ-formed enol species induced by the formation of a more stable conjugate diene moiety. The functional group tolerances were investigated by using a series of readily available substrates. A plausible mechanism has been proposed based on the evidence of the capture of the hemiaminal intermediate. Lastly, a Büchi ketone, which is the pivotal intermediate in the synthesis of the indole alkaloid vindorosine, was synthesized by utilizing our newly developed methodology.
- Wang, Yanshi,Lin, Jingsheng,Wang, Xiaoyu,Wang, Guanghui,Zhang, Xinhang,Yao, Bo,Zhao, Yuandong,Yu, Pengfei,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
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supporting information
p. 4026 - 4032
(2018/01/15)
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- Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids
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A highly enantioselective tandem Michael addition of tryptamine-derived oxindoles to alkynones was developed by taking advantage of a chiral N,N′-dioxide Sc(OTf)3 catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine-3,3′-oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(?)-tubifoline, (?)-tubifolidine, (?)-dehydrotubifoline] was achieved in 10–11 steps.
- He, Weigang,Hu, Jiadong,Wang, Pengyan,Chen, Le,Ji, Kai,Yang, Siyu,Li, Yin,Xie, Zhilong,Xie, Weiqing
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supporting information
p. 3806 - 3809
(2018/03/05)
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- Enantioselective Synthesis of trans-Vicinal Diamines via Rhodium-Catalyzed [2+2] Cycloaddition of Allenamides
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An efficient protocol for the enantioselective Rh-catalyzed intermolecular head-to-head [2+2] cycloaddition of allenamides was developed. A variety of enantio-enriched cyclobutane-1,2-diamine derivatives were achieved in good yields with good to excellent enantioselectivities. (Figure presented.).
- Zheng, Wei-Feng,Sun, Gui-Jun,Chen, Liang,Kang, Qiang
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supporting information
p. 1790 - 1794
(2018/04/02)
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- Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis
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The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-β-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.
- Cera, Gianpiero,Lanzi, Matteo,Balestri, Davide,Della Ca, Nicola,Maggi, Raimondo,Bigi, Franca,Malacria, Max,Maestri, Giovanni
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supporting information
p. 3220 - 3224
(2018/06/11)
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- One-pot synthesis of tricyclo-1,4-benzoxazines via visible-light photoredox catalysis in continuous flow
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A facile one-pot synthesis of tricyclo-1,4-benzoxazines has been developed via metal-free intramolecular cyclization of indole derivates. These reactions were efficiently achieved at ambient temperature by using visible-light photoredox catalysis in conti
- Wu, Guolin,Lv, Tingting,Mo, Wenhui,Yang, Xiping,Gao, Yu,Chen, Haijun
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supporting information
p. 1395 - 1398
(2017/03/16)
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- A simple and efficient method for constructing azepino[4,5-b]indole derivatives via acid catalysis
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A new synthetic methodology has been developed to prepare the biologically important azepino[4,5-b]indole derivatives under Br?nsted acid catalysis. The notable features of this protocol include its operational simplicity, high reaction yields and environmentally benign and mild reaction conditions.
- Kumar Boominathan, Siva Senthil,Reddy, Mutra Mohana,Hou, Ruei-Jhih,Chen, Hui-Fen,Wang, Jeh-Jeng
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supporting information
p. 1872 - 1875
(2017/03/09)
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- Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds
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An efficient synthesis of tetrahydrocarboline-type products and polycyclic spiroindolines has been achieved. The transformation proceeds via rhodium(II)-catalyzed intramolecular annulations of indolyl- and pyrrolyl-tethered N-sulfonyl-1,2,3-triazoles. The reaction could be tuned toward either the formal [3 + 2] cycloaddition or the C-H functionalization reaction depending on the electronic and structural features of the substrates, leading to the production of a variety of structurally related heterocyclic compounds.
- Fu, Liangbing,Davies, Huw M. L.
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supporting information
p. 1504 - 1507
(2017/04/13)
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- Exploiting the σ-phylic properties of cationic gold(i) catalysts in the ring opening reactions of aziridines with indoles
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A study on the SN2-type ring opening reactions of aziridines with indoles as nucleophiles is reported. Under gold(i) catalysis a great variety of tryptamine derivatives were prepared in good to excellent yields with complete stereocontrol when chiral aziridines were used. We demonstrated that cationic gold(i) catalysts are superior Lewis acids to the previously reported group 3, 12 and 13 metals in terms of catalyst loading and reaction yields. Moreover, complete regioselectivity was observed for 2-phenyl-N-tosylaziridine; whereas, regioselectivity up to 10:1 ratio was observed with 2-methyl-N-tosylaziridine. Finally, a preliminary study on the dearomatization reactions giving rise to pyrroloindolines is also reported.
- Rossi, Elisabetta,Abbiati, Giorgio,Dell'Acqua, Monica,Negrato, Marco,Paganoni, Andrea,Pirovano, Valentina
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p. 6095 - 6110
(2016/07/06)
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- Dearomatization of Indoles via Palladium-Catalyzed Allylic C-H Activation
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The first Pd-catalyzed allylic dearomatization of substituted indoles triggered by C-H bond activation is reported. The presence of a catalytic amount of 2,5-DMBQ is proven to be a key factor for the high yield. This one-pot tandem allylic C-H activation/dearomatization sequence provides a straightforward access to 3,3-disubstituted indolines.
- Zhang, Heng,Hu, Rong-Bin,Liu, Na,Li, Shi-Xia,Yang, Shang-Dong
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supporting information
p. 28 - 31
(2016/01/15)
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- Gold-Catalyzed Intramolecular Tandem Cyclization of Indole-Ynamides: Diastereoselective Synthesis of Spirocyclic Pyrrolidinoindolines
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A gold-catalyzed intramolecular tandem cyclization of indole-ynamide affords tetracyclic spirocyclic pyrrolidinoindoline bearing an all-carbon quaternary stereocentre in a single step; however, when the reaction was carried out in the presence of BF3·Et2O, the corresponding tricyclic spirocyclic pyrrolidinoindoline-based enones are produced through a key 1,5-hydride shift. The developed chemistry provides a diastereoselective and straightforward entry to structurally diverse polycylic pyrrolidinoindolines from indole-ynamides in one-pot reactions under mild conditions.
- Zheng, Nan,Chang, Yuan-Yuan,Zhang, Li-Jie,Gong, Jian-Xian,Yang, Zhen
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supporting information
p. 371 - 375
(2016/05/19)
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- Access to Spirocyclized Oxindoles and Indolenines via Palladium-Catalyzed Cascade Reactions of Propargyl Carbonates with 2-Oxotryptamines and Tryptamines
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(Chemical Equation Presented). Reported here are methods for the direct construction of a range of spirocyclized oxindoles and indolenines in good to excellent yields. Specifically, we report the palladium-catalyzed reactions of oxindoles and indoles, both functioning as bis-nucleophiles, with propargyl carbonates to afford spirocyclic products having an exocyclic double bond on the newly formed ring. The reaction proceeds through a process wherein the first nucleophilic unit on the oxindole or indole reacts with an allenyl-palladium species, formed from oxidative addition of Pd(0) to propargyl carbonates, to generate a π-allyl palladium intermediate that then reacts further with the second nucleophilic component of the oxindole or indole. The cascade process forges two bonds en route to spirocyclized oxindole and indolenine products. The use of chiral phosphines renders the cyclization sequence enantioselective, providing spirocyclic products with modest to good enantioselectivities.
- Nibbs, Antoinette E.,Montgomery, Thomas D.,Zhu, Ye,Rawal, Viresh H.
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p. 4928 - 4941
(2015/06/02)
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- CuCl2/TBHP-mediated direct chlorooxidation of indoles
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CuCl2/TBHP-mediated direct chlorooxidation of indole derivatives under simple aerobic conditions was reported, leading to facile preparations of a range of 3,3-disubstituted 3-chlorooxindoles in good yields and selectivities.
- Wang, Huifei,Liu, Dong,Chen, Huiyu,Li, Jing,Wang, David Zhigang
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supporting information
p. 7073 - 7076
(2015/08/19)
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- Palladium-Catalyzed Allylic Amination of Homoallylic Alcohols with Amines via Carbon-Carbon Bond Cleavage
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An efficient approach for palladium(II) acetate catalyzed allylic amination of homoallylic alcohols with various amines via sequential retro-allylation and amination was developed, which afforded the corresponding allylic amines in up to 98% yield.
- Sun, Gui-Jun,Wang, Yong,Kang, Qiang
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supporting information
p. 2931 - 2936
(2015/09/28)
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- Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate
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We report the intermolecular palladium-catalyzed reaction of tert-butyl propargyl carbonate with tryptamine derivatives or other indole-containing bis-nucleophiles. The reaction proceeds under mild conditions and with low catalyst loadings to afford novel spiroindolenine products in good to high yields.
- Montgomery, Thomas D.,Nibbs, Antoinette E.,Zhu, Ye,Rawal, Viresh H.
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supporting information
p. 3480 - 3483
(2014/07/21)
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- A novel neutral organic electron donor with record half-wave potential
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Tricyclic donor 26 has been prepared and is the most reducing neutral ground-state organic molecule known, with an oxidation potential 260 mV more negative than the previous record. Cyclic voltammetry shows that a 2-electron reversible redox process occurs in DMF as solvent at -1.46 V vs. Ag/AgCl.
- Farwaha, Hardeep S.,Bucher, Goetz,Murphy, John A.
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p. 8073 - 8081
(2013/12/04)
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- Design and bio-evaluation of indole derivatives as potent Kv1.5 inhibitors
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Atrial fibrillation (AF) is one of the common arrhythmias that threaten human health. Kv1.5 potassium channel is reported as an efficacious and safe target for the treatment of AF. In this paper, we designed and synthesized three series of compounds through modifying the lead compound RH01617 that was screened out by the pharmacophore model we reported earlier. All of the compounds were evaluated by the whole-patch lamp technology and most of them possessed potent inhibitory activities against Kv1.5. Compounds IIIi and IIIl were evaluated for the target selectivity as well as the pharmacodynamic effects in an isolated rat model. Due to the promising pharmacological behavior, compound IIIl deserves further pharmacodynamic and pharmacokinetic evaluations.
- Guo, Xiaoke,Yang, Qian,Xu, Jing,Zhang, Li,Chu, Hongxi,Yu, Peng,Zhu, Yingying,Wei, Jinglian,Chen, Weilin,Zhang, Yaozhong,Zhang, Xiaojin,Sun, Haopeng,Tang, Yiqun,You, Qidong
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p. 6466 - 6476
(2013/10/22)
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- Rhodium(I)-catalyzed cycloisomerization of nitrogen-tethered indoles and alkylidenecyclopropanes: Convenient access to polycyclic indole derivatives
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At the end of its tether: A new synthetic protocol for the preparation of polycyclic indole derivatives has been developed from a rhodium(I)-catalyzed cycloisomerization of a nitrogen-tethered indole and alkylidenecyclopropane, affording the corresponding
- Zhang, Di-Han,Tang, Xiang-Ying,Wei, Yin,Shi, Min
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supporting information
p. 13668 - 13673
(2013/10/22)
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- Domino heck-aza-michael reactions: efficient access to 1-substituted tetrahydro-β-carbolines
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"Chemical Equation Presentation" A simple and efficient palladium-catalyzed domino reaction for the synthesis of a series of C1-substituted tetrahydro-β-carbolines is described. This domino process involves a Heck reaction at the indole 2-position of a ha
- Priebbenow, Daniel L.,Henderson, Luke C.,Pfeffer, Frederick M.,Stewart, Scott G.
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supporting information; experimental part
p. 1787 - 1790
(2010/05/01)
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- Ruthenium-catalyzed /V-alkylation of amines and sulfonamides using borrowing hydrogen methodology
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The alkylation of amines by alcohols has been achieved using 0.5 mol percent [Ru(p-cymene)CI2]2 with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. A/-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols requiremore forcing conditions than primary alcohols but are still effective a lkylating agents in the presence of this catalyst.
- Hamid, M. Haniti S. A.,Allen, C. Liana,Lamb, Gareth W.,Maxwell, Aoife C.,Maytum, Hannah C.,et al.
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supporting information; experimental part
p. 1766 - 1774
(2009/07/25)
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- Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold
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Indoles react intramolecularly with alkynes in the presence of gold catalysts to give from six- to eight-membered-ring annulated compounds. The cationic AuI complex [Au(P{C6H4-(o-Ph))(tBu) 2)(NCMe)]SbF6 is the best catalyst for the formation of six- and seven-membered rings by 6-endo-dig, 6-exo-dig, and 7-exo-dig cyclizations. Indoloazocines are selectively obtained with AuCl3 as catalyst in a rare 8-endodig process. In this process alienes or tetracyclic annulated derivatives are also formed as a result of an initial fragmentation reaction. The intermolecular reaction of indoles with alkynes proceeds to form 3-alkenylated intermediates that react with a second equivalent of indole to give bisindolyl derivatives. Indoles that are substituted at the 3-position react intermolecularly with alkynes to give 2-alkenylated intermediates that can be trapped intramolecularly with the appropriate nucleophiles.
- Ferrer, Catalina,Amijs, Catelijne H. M.,Echavarren, Antonio M.
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p. 1358 - 1373
(2008/02/04)
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- Inhibitors of 15-lipoxygenase
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The present invention provides inhibitors of 15-LO according to Formula I, pharmaceutical compositions containing such inhibitors and methods for treating diseases related to the 15-LO cascade using such compounds and compositions.
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Page/Page column 9
(2008/06/13)
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- Tandem hydroformylation-hydrazone formation-Fischer indole synthesis: A novel approach to tryptamides
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A novel one-pot synthesis of indole systems via tandem hydroformylation-hydrazone formation-Fischer indolization starting from allylic amides and aryl hydrazines is described. This tandem procedure directly leads to biologically interesting tryptamides and analogues. The Royal Society of Chemistry 2005.
- Schmidt, Axel M.,Eilbracht, Peter
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p. 2333 - 2343
(2007/10/03)
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- Catalytic N-sulfonyliminium ion-mediated cyclizations to α-vinyl-substituted isoquinolines and β-carbolines and applications in metathesis
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Catalytic Sn(OTf)2-induced cyclization of linear, aryl-containing allylic N,O-acetals produced vinyl-substituted tetrahydroisoquinolines and tetrahydro-1H-β-carbolines. The usefulness of the vinyl moiety in the resulting products was demonstrated via the synthesis of various key building blocks for alkaloid structures. The α-vinyl moiety was utilized in a [2,3] sigmatropic rearrangement, in ring-closing metathesis and a cross-metathesis-based synthesis of vincantril, an antianoxia agent, and a synthetic member of the vincamine type natural products.
- Kinderman, Sape S.,Wekking, Monique M. T.,Van Maarseveen, Jan H.,Schoemaker, Hans E.,Hiemstra, Henk,Rutjes, Floris P. J. T.
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p. 5519 - 5527
(2007/10/03)
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- Bronsted acid-catalyzed highly stereoselective arene-ynamide cyclizations. A novel keteniminium Pictet-Spengler cyclization in total syntheses of (±)-desbromoarborescidines A and C
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(Chemical Equation Presented) A Bronsted acid-catalyzed highly stereoselective arene-ynamide cyclization is described. These reactions constitute a keteniminium variant of Pictet-Spengler cyclizations, leading to efficient synthesis of nitrogen heterocycl
- Zhang, Yanshi,Hsung, Richard P.,Zhang, Xuejun,Huang, Jian,Slafer, Brian W.,Davis, Allison
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p. 1047 - 1050
(2007/10/03)
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- Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase
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A series of inhibitors of mammalian 15-lipoxygenase based on tryptamine and homotryptamine scaffolds is described. Compounds with aryl substituents at C-2 of the indole core of tryptamine and homotryptamine sulfonamides (e.g., 37a-p) proved to be potent i
- Weinstein, David S.,Liu, Wen,Gu, Zhengxiang,Langevine, Charles,Ngu, Khehyong,Fadnis, Leena,Combs, Donald W.,Sitkoff, Doree,Ahmad, Saleem,Zhuang, Shaobin,Chen, Xing,Wang, Feng-Lai,Loughney, Deborah A.,Atwal, Karnail S.,Zahler, Robert,Macor, John E.,Madsen, Cort S.,Murugesan, Natesan
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p. 1435 - 1440
(2007/10/03)
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- Model studies related to the total synthesis of the fumitremorgins; the Pictet-Spengler cyclisation and the formation and intramolecular acylation of a 1,2-dihydro-β-carboline derivative
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The preparations of the tetrahydro-β-carbolines 8, 9b, and 9d are described. The Pictet-Spengler reaction of L-tryptophyl-L-proline methyl ester with 3-methylbutanal gave the tetrahydro-β-carbolines 20 and 21; subsequent acid-catalysed cyclisation afforded the fumitremorgin analogues 22 and 23. The 2-(p-toluenesulphonyl)tetrahydro-β-carboline 27a furnished the unsaturated pentacycle 28a upon treatment with alkali.
- Harrison, David M.,Sharma, Ram Bilas
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p. 3165 - 3184
(2007/10/02)
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- 2-halogen-substituted N-indolylethyl-sulphonamides and inhibiting platelet aggregation and antagonizing thromboxane A2 therewith
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Inhibiting platelet aggregation and antagonizing thromboxane A2 with new 2-halogen-substituted N-indolyethyl-sulphonamides of the formula STR1 in which R1 represents hydrogen, halogen, trifluoromethyl, carboxyl or alkoxycarbonyl havi
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- Reactions with Aziridines, 52. - Branched-Chain Tryptamine Compounds from Indolyllithium and Activated Aziridines
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Reaction of indolyllithium 1 with activated aziridines 2 in toluene provides the tryptamines 3 or 4 in good yields. - Key Words: Nucleophilic ring opening / Regioselectivity / Ambident nucleophiles / Aziridines / Tryptamine
- Onistschenko, Andreas,Stamm, Helmut
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p. 2397 - 2398
(2007/10/02)
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- Electroorganic Chemistry. 81. Anodic Oxidation of Sulfonamides and Amidophosphates
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Oxidation peak potentials of sulfonamides and amidophosphates were measured in acetonitrile and compared with the corresponding amides and carbamates.The results showed that the order of easiness of oxidation was amides > carbamates > amidophosphates > sulfonamides.Furthermore, the reaction of silyl enol ethers or trimethyl phosphite with anodically α-methoxylated sulfonamides or amidophosphates has clearly shown that the α-methoxylated compounds are useful starting materials in organic synthesis.For example, optically active L-tryptophan was synthesized from α-methoxylated N-(p-tolylsulfonyl)-L-proline ester.
- Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji,Uchida, Kenshi,Kanazawa, Takenobu,Tsuda, Kunio
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p. 3711 - 3716
(2007/10/02)
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- A GENERAL METHOD FOR THE SYNTHESIS OF INDOLES BEARING A VARIETY OF SUBSTITUENTS AT THE β-POSITION, AND ITS APPLICATION TO THE SYNTHESIS OF L-TRYPTOPHAN
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A general synthetic method of β-substituted indoles such as indolacetic acid, tryptamine and L-tryptophan has been exploited utilizing α-methoxylated amides, lactams, a carbamate, and sulfonamides, easily obtainable by an electrochemical method, as key intemediates.
- Shono, Tatsuya,Matsumura, Yoshihiro,Kanazawa, Takenobu
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p. 1259 - 1262
(2007/10/02)
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