- Reactions of 1-tosyl-3-substituted indoles with conjugated dienes under thermal and/or high-pressure conditions
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The behavior of 1-tosyl-3-acetylindole (1a), N,N-diethyl-17tosyl-3-indoleglyoxylamide (1b), and 1-tosyl-3-nitroindole (1c) as dienophiles in Diels-Alder reactions under thermal and/or high-pressure conditions was explored with different dienes: isoprene (
- Biolatto,Kneeteman,Paredes,Mancini
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Read Online
- Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls
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Transition metal-catalyzed diamination by hydroxylamines is a common approach for making three-membered aziridines, while its use for building the larger N-heterocycles is still underdeveloped. Herein, we report an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation of o-bromo(or chloro)-biaryls with bifunctional secondary hydroxylamines for the one-step assembly of synthetically useful carbazoles. Noteworthily, a linchpin for this domino reaction was the judicious selection of both the amino-sources and Pd(0)-catalysts for enabling the prerequisite oxidative addition of aryl halides to Pd(0)-species in the presence of hydroxylamines with a labile N-O bond. [Figure not available: see fulltext.].
- Bai, Jiaxing,Ding, Pin,Han, Lingbo,Liu, Jingjing,Luan, Xinjun
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- Method for electrochemically synthesizing carbazole compounds
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The invention relates to a method for electrochemical synthesis of a carbazole compound. The method comprises the following steps: taking an N-substituted acylamino biphenyl derivative as a substrate,adding the substrate and an electrolyte into an organic
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Paragraph 0098-0102
(2021/11/27)
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- Electrochemical Palladium-Catalyzed Intramolecular C—H Amination of 2-Amidobiaryls for Synthesis of Carbazoles
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The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C—H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.
- Gao, Xinlong,Lei, Aiwen,Wang, Pan,Wang, Qingqing,Zhang, Heng,Zhang, Xiaojing
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supporting information
p. 143 - 148
(2020/12/18)
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- Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
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Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.
- Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
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supporting information
p. 13481 - 13494
(2020/12/15)
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- Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?
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Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.
- Chen, Xiao-Yue,Huang, Yu-Hao,Zhou, Jian,Wang, Peng
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supporting information
p. 1269 - 1272
(2020/08/13)
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- Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring
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Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).
- Qiang-Liu,Liu, Yu-Xiu,Song, Hong-Jian,Wang, Qing-Min
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supporting information
p. 3110 - 3115
(2020/07/04)
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- Preparation method of carbazole compound
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The invention relates to a preparation method of a carbazole compound. The method comprises the following steps: adding a reaction substrate as shown in a formula (III) into a solvent for dissolving,adding cyclic diacyl peroxide and transition metal, and
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Paragraph 0034-0042; 0052-0063; 0065-0078
(2020/08/17)
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- Scalable Electrochemical Transition-Metal-Free Dehydrogenative Cross-Coupling Amination Enabled Alkaloid Clausines Synthesis
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Reported herein is an environmentally benign electrochemical C?H bond dehydrogenative amination protocol for the construction of privileged carbazole moiety with broad generality. Preliminary mechanistic investigations implied a radical reaction pathway.
- Zhang, Pan,Li, Baoying,Niu, Liwei,Wang, Ling,Zhang, Guofeng,Jia, Xiaofei,Zhang, Guoying,Liu, Siyuan,Ma, Li,Gao, Wei,Qin, Dawei,Chen, Jianbin
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supporting information
p. 2342 - 2347
(2020/05/05)
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- Compound taking tri-carbazole as core and application thereof in organic electroluminescence device
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The invention discloses a compound taking tri-carbazole as a core and an application thereof in an organic electroluminescence device. The compound taking tri-carbazole as the core has the characteristics of being unlikely to crystallize and gather among
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Paragraph 0044; 0047; 0050
(2018/07/30)
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- Triazine derivative and application thereof on organic electroluminescence device
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The invention discloses a triazine derivative and application thereof on an organic electroluminescence device. The compound takes triazine as a core and has the characteristics of difficulty in crystallization among molecules, difficulty in aggregation a
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Paragraph 0058; 0061
(2018/07/30)
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- The carbazole compound manufactured by the manufacturing method in the carbazole compound.
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PROBLEM TO BE SOLVED: To provide a more simple method of manufacturing carbazoles which can be used industrially.SOLUTION: There is provided a manufacturing method of carbazoles including reacting 2-aminobiphenyls of which an amino group is represented by the formula (1), -NHR(1), where Rrepresents S(=O)R, C(=O)Ror an alkyl group having 1 to 3 carbon atoms, where Rrepresents a phenyl group may be substituted by an alkyl group having 1 to 2 carbon atoms or a nitro group, or an alkyl group having 1 to 3 carbon atoms, Rrepresents an alkyl group having 1 to 5 carbon atoms, with a sulfur-based solvent and oxygen in a presence of a heterogeneous catalyst carrying palladium, for example [P9-Type][UL-Type][P60-Type] provided by N.E. CHEMCAT CORPORATION and the like, at 110 to 130°C.
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Paragraph 0037-0040
(2020/10/19)
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- Silver-copper co-catalyzed cascade intramolecular cyclization/desulfinamide/dehydrogenation: One-pot synthesis of substituted carbazoles
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Herein, a silver and copper co-catalyzed cascade intramolecular cyclization/desulfinamide/dehydrogenation reaction for the synthesis of substituted carbazoles is reported. This reaction, which involved formation of new C-C and C-N bonds as well as C-N bond cleavage, afforded diverse carbazoles in high yields and showed good functional group tolerance.
- Huang, Yuanqiong,Guo, Zhonglin,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
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p. 7143 - 7146
(2018/07/05)
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- Design, synthesis and biological evaluation of: N -arylsulfonyl carbazoles as novel anticancer agents
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In this work, a set of structurally diverse synthetic carbazoles was screened for their anticancer activities. According to structure-activity relationship studies, carbazoles with an N-substituted sulfonyl group exhibited better anticancer activity. Moreover, compound 8h was discovered to show the most potent anticancer effects on Capan-2 cells by inducing apoptosis and cell cycle arrest in G2/M phase. Finally, the in vivo study demonstrated that 8h prevented the tumor growth in PANC-1 and Capan-2 xenograft models without apparent toxicity.
- You, Xin,Zhu, Daqian,Lu, Wenhua,Sun, Yichen,Qiao, Shuang,Luo, Bingling,Du, Yongliang,Pi, Rongbiao,Hu, Yumin,Huang, Peng,Wen, Shijun
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p. 17183 - 17190
(2018/05/28)
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- Blue-light TADF (thermally activated delayed fluorescence) aromatic material containing carbazole dendrites, method for preparing warm white device from blue-light TADF aromatic material and application of blue-light TADF aromatic material
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The invention relates to a blue-light TADF (thermally activated delayed fluorescence) aromatic material containing carbazole dendrites, a method for preparing a warm white device from the blue-light TADF aromatic material and an application of the blue-li
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Paragraph 0155; 0156; 0157; 0158; 0159; 0176
(2017/10/22)
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- Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5 + 2] Annulation of o-Arylanilines with Dienes
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An efficient method for the construction of dibenzo[b,d]azepines containing two distinct stereogenic elements in a highly diastereoselective fashion is described. The key of the [5 + 2] reaction is to form a π-allylpalladium species through sequential C-H
- Bai, Lu,Wang, Yan,Ge, Yicong,Liu, Jingjing,Luan, Xinjun
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supporting information
p. 1734 - 1737
(2017/04/11)
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- Palladium on Carbon-Catalyzed C?H Amination for Synthesis of Carbazoles and its Mechanistic Study
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10% Palladium on carbon (10% Pd/C) successfully catalyzed the intramolecular C?H amination of various N-mesylated 2-aminobiphenyls in the presence of a catalytic amount of pyridine N-oxide in heated dimethyl sulfoxide (DMSO) under an oxygen atmosphere to afford the corresponding N-mesylcarbazoles. The reaction would proceed via a single-electron transfer process based on its significant suppression by the addition of a single-electron scavenger, tetracyanoquinodimethane (TCNQ), and the substituents on the aromatic rings of the substrate have an insignificant effect on the reaction progress. (Figure presented.).
- Monguchi, Yasunari,Okami, Hiroki,Ichikawa, Tomohiro,Nozaki, Kei,Maejima, Toshihide,Oumi, Yasunori,Sawama, Yoshinari,Sajiki, Hironao
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p. 3145 - 3151
(2016/10/09)
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- Synthesis of Carbazoles by a Merged Visible Light Photoredox and Palladium-Catalyzed Process
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Carbazoles have attracted great interest in recent years for a variety of applications in organic and medicinal chemistry as well as in materials science. In this work, an efficient method for the synthesis of carbazoles through the intramolecular C-H bon
- Choi, Sungkyu,Chatterjee, Tanmay,Choi, Won Joon,You, Youngmin,Cho, Eun Jin
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p. 4796 - 4802
(2015/08/18)
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- Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams
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The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.
- Laha, Joydev K.,Jethava, Krupal P.,Dayal, Neetu
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p. 8010 - 8019
(2015/03/18)
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- PdII-catalyzed Di-o-olefination of carbazoles directed by the protecting N-(2-pyridyl)sulfonyl group
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Despite the significance of carbazole in pharmacy and material science, examples of the direct C-H functionalization of this privileged unit are quite rare. The N-(2-pyridyl)sulfonyl group enables the PdII-catalyzed ortho-olefination of carbazo
- Urones, Beatriz,Arrayás, Ramón Gómez,Carretero, Juan Carlos
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supporting information
p. 1120 - 1123
(2013/03/29)
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- Synthesis of carbazoles via one-pot copper-catalyzed amine insertion into cyclic diphenyleneiodoniums as a strategy to generate a drug-like chemical library
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Carbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by cop- per(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfon amides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT-22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.
- Zhu, Daqian,Liu, Qi,Luo, Bingling,Chen, Meihui,Pi, Rongbiao,Huang, Peng,Wen, Shijun
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p. 2172 - 2178
(2013/10/01)
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- Palladium-catalyzed oxidative insertion of carbon monoxide to N -sulfonyl-2-aminobiaryls through C-H bond activation: Access to bioactive phenanthridinone derivatives in one pot
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Palladium-catalyzed oxidative carbonylation of N-sulfonyl-2-aminobiaryls through C-H bond activation and C-C, C-N bond formation under TFA-free and milder conditions has been developed. The reaction tolerates a variety of substrates and provides biologically important phenanthridinone derivatives in yields up to 94%.
- Rajeshkumar, Venkatachalam,Lee, Tai-Hua,Chuang, Shih-Ching
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p. 1468 - 1471
(2013/06/26)
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- Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity
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Carbazole moiety is an important scaffold with a variety of biological applications, for example, anti-oxidative stress. Our previous synthesized carbazoles were screened for their neuroprotective properties against two individual oxidative stresses. Some of the new carbazole derivatives were observed with modest to good neuroprotective effects on neuronal cells HT22 against cell injury induced by glutamate or homocysteic acid (HCA). Substituents introduced to the carbazole ring system play crucial roles in their biological activities. In particular, a bulky group favors the neuroprotective activity of the compounds. One of the new compounds, 6, showed the best neuroprotective effects, which might result from its anti-oxidative activity with a GSH-independent mechanism. These findings might provide an alternative strategy for the development of novel carbazole derivatives for the treatment of CNS diseases such as Alzheimer's disease.
- Zhu, Daqian,Chen, Meihui,Li, Min,Luo, Bingling,Zhao, Yang,Huang, Peng,Xue, Fengtian,Rapposelli, Simona,Pi, Rongbiao,Wen, Shijun
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- A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade as a key step
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The indole alkaloid α-cyclopiazonic acid 1 has been synthesised by a route, which features at its core an acid-catalysed cationic cascade cyclisation terminated by a sulfonamide group.
- Griffiths-Jones, Charlotte M.,Knight, David W.
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experimental part
p. 8515 - 8528
(2011/11/29)
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- Pd-catalyzed intramolecular oxidative C-H amination: Synthesis of carbazoles
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A Pd-catalyzed oxidative C-H amination of N-Ts-2-arylanilines under ambient temperature using Oxone as an inexpensive, safe, and easy-to-handle oxidant has been developed. This process represents a green and practical method for the facile construction of carbazoles with a broad substrate scope and wide functional group tolerance.
- Youn, So Won,Bihn, Joon Hyung,Kim, Byung Seok
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supporting information; experimental part
p. 3738 - 3741
(2011/09/13)
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- Microwave-assisted reactions of nitroheterocycles with dienes. Diels-Alder and tandem hetero Diels-Alder/[3,3] sigmatropic shift
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Diels-Alder cycloaddition of 3-nitro-1-(p-toluenesulfonyl)indole 1 with dienes 2-6 under microwave irradiation in solvent-free conditions gave carbazole derivatives after elimination of the nitro group and in situ aromatization. While 3-nitro-1-(p-toluene
- Victoria Gómez,Aranda, Ana I.,Moreno, Andrés,Cossío, Fernando P.,de Cózar, Abel,Díaz-Ortiz, ángel,de la Hoz, Antonio,Prieto, Pilar
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experimental part
p. 5328 - 5336
(2009/11/30)
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- Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
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An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps.
- Liu, Zhijian,Larock, Richard C.
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p. 347 - 355
(2007/10/03)
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- Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles
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A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process directly leads to N-sulfonyl pyrroles, indoles and carbazoles. The selection of an appropriate reac
- Abid, Mohammed,Teixeira, Liliana,T?r?k, Béla
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p. 4047 - 4050
(2008/02/02)
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- Diels-Alder reactions of N-tosyl-3-nitroindole and dienamides: Synthesis of intermediates of Aspidospermine alkaloids
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N-tosyl-3-nitroindole undergoes high yielding Diels-Alder reactions with 1-(N-acyl-N-alkylamino)-1,3-butadienes in a regioselective manner, to afford advanced intermediates for the synthesis of Aspidospermine alkaloids.
- Biolatto, Betina,Kneeteman, Maria,Mancini, Pedro
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p. 3343 - 3346
(2007/10/03)
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- PHOTO-FRIES REARRANGEMENTS IN N-SULPHONYL CARBAZOLES
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When photo-Fries rearrangements in N-sulphonyl carbazoles 1 in benzene or methanol smoothly afforded 1- and 3- sulphonylcarbazoles 2 and 3 respectively in 29-55percent yield, N-benzoylcarbazole 1d did not undergo similar rearrangements to give the expected products.
- Chakrabati, Amit,Biswas, Goutam K.,Chakraborty, D. P.
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p. 5059 - 5064
(2007/10/02)
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