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Selective synthesis of 7-ester indoles and bis-indoles
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作者 WANG Yong-hui 《化学研究与应用》 北大核心 2025年第10期3201-3208,共8页
multi-component reaction was reported for the synthesis of 7-ester indoles and bis-indoles under microwave-assisted conditions,enriching and expanding the library of heterocyclic compounds.This reaction started from e... multi-component reaction was reported for the synthesis of 7-ester indoles and bis-indoles under microwave-assisted conditions,enriching and expanding the library of heterocyclic compounds.This reaction started from enamine ketone,aromatic ketone aldehyde hydrate,and carboxylic acid,and selectively synthesized 7-ester indoles and bis-indoles by changing the substituted enamine ketone substrate.This method had the characteristics of high regional selectivity,short reaction time,and green environmental protection. 展开更多
关键词 microwave radiation 7-ester indoles bis-indoles
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Photoinduced Difluoromethylation/Cyclization of 2-Aryl Indoles with HCF_(2)SO_(2)Na
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作者 Jiang Jie Li Jiali +3 位作者 Pan Ruohan Chen Yu Liu Jiale Tang Yucai 《有机化学》 北大核心 2025年第4期1239-1248,共10页
Difluoromethyl compounds are widely found in natural products,bioactive molecule and pharmaceuticals.A visible-light induced difluoromethylation/cyclization of 2-aryl indoles is described to construct indolo[2,1-a]iso... Difluoromethyl compounds are widely found in natural products,bioactive molecule and pharmaceuticals.A visible-light induced difluoromethylation/cyclization of 2-aryl indoles is described to construct indolo[2,1-a]isoquinolin-6(5H)-one derivatives using the inexpensive and easy-to-handle HCF_(2)SO_(2)Na as an HCF2 sources.Diverse difluoromethylated indolo[2,1-a]isoquinolines were readily obtained in moderate to good yields.Mechanistic studies demonstrate that the reaction may involve a radical process. 展开更多
关键词 difluoromethyl compounds visible-light 2-aryl indoles difluoromethylation/cyclization
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Facile synthesis of C2 or C3-(cycloheptatrienyl)-substituted indoles
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作者 PANG Jinyu YAO Chunna WU Bin 《中南民族大学学报(自然科学版)》 2025年第2期201-212,共12页
Cycloheptatriene is a privileged structural motif present in many bioactive compounds,pharmaceutical agents and natural products,especially in a large number of core structures of sesquiterpenoids.Herein,a mild and ef... Cycloheptatriene is a privileged structural motif present in many bioactive compounds,pharmaceutical agents and natural products,especially in a large number of core structures of sesquiterpenoids.Herein,a mild and efficient synthetic approach was reported for access of a series of C2 or C3-(cycloheptatrienyl)-substituted indoles.A wide range of functional groups can be well tolerated in this transformation,especially including hydroxyl,halo,carboxylic acid and its derivative groups.Based on these results,a rational mechanism via electrophilic substitution of indoles with tropylium tetrafluoroborate is proposed. 展开更多
关键词 cycloheptatriene INDOLE TROPYLIUM SYNTHESIS
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A convenient one-pot three component synthesis of 3-aminoalkylated indoles catalyzed by 3-chlorophenylboronic acid 被引量:6
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作者 Santosh V.Goswami Prashant.B.Thorat +2 位作者 Vijay N.Kadam Sachin A.Khiste Sudhakar R.Bhusare 《Chinese Chemical Letters》 SCIE CAS CSCD 2013年第5期422-424,共3页
An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3- chlorophenylboronic acid as a catalyst under ambient temperature conditions.The three-component reaction of indoles,aromatic a... An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3- chlorophenylboronic acid as a catalyst under ambient temperature conditions.The three-component reaction of indoles,aromatic aldehydes and N-methyl aniline offered corresponding 3-aminoalkylated indoles in excellent yields.This protocol presents some remarkable features such as mild reaction conditions,simple workup procedure and excellent yields. 展开更多
关键词 3-Aminoalkylaed indoles 3-Chlorophenylboronic acid Aromatic aldehyde N-METHYLANILINE indoles
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New Greener Alternative for Biocondensation of Aldehydes and Indoles Using Lemon Juice: Formation of Bis-, Tris-, and Tetraindoles 被引量:1
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作者 Rammohan Pal 《International Journal of Organic Chemistry》 2013年第2期136-142,共7页
This work presents a new greener alternative for biocondensation of aldehydes and indoles for the synthesis of bis- and tris(indolyl)methanes catalyzed by lemon juice (Citrus limon) in good yields under ultrasound irr... This work presents a new greener alternative for biocondensation of aldehydes and indoles for the synthesis of bis- and tris(indolyl)methanes catalyzed by lemon juice (Citrus limon) in good yields under ultrasound irradiation in aqueous ethanol. Various substituted aldehydes with indoles under this reaction condition are elucidated. Also, tetraindolyl compounds were prepared using terephthaldialdehyde by following the same protocol. This method is an environmentally benign, efficient reaction, which requires shorter reaction time and simple experimental and work-up procedures. 展开更多
关键词 Citrus limon JUICE Biocondensation ALDEHYDES indoles Aqueous Ethanol Sonication Bis- Tris- Tetraindoles
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Asymmetric synthesis of pyrrolo[1,2-a]indoles via organocatalytic[3+2]annulation of substituted 2-vinylindoles with azlactones
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作者 Wulin Yang Hao Wang +2 位作者 Zirong Pan Zhong Li Weiping Deng 《Chinese Chemical Letters》 SCIE CAS CSCD 2020年第3期721-724,共4页
The chiral phosphoric acid catalyzed asymmetric[3+2]annulation of substituted 2-vinylindoles with azlactones has been established.This reaction represented a practical approach for the synthesis of structurally divers... The chiral phosphoric acid catalyzed asymmetric[3+2]annulation of substituted 2-vinylindoles with azlactones has been established.This reaction represented a practical approach for the synthesis of structurally diverse pyrrolo[1,2-a]indoles with two vicinal stereocenters including one tetrasubstituted stereocenter in good yields and good stereoselectivities under mild conditions. 展开更多
关键词 [3+2]Annulation AZLACTONES 2-Vinylindoles ASYMMETRIC ORGANOCATALYSIS Pyrrolo[1 2-a]indoles Chiral phosphoric acid
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Reactivity of Indoles through the Eyes of a Charge-Transfer Partitioning Analysis 被引量:1
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作者 OROZCO-VALENCIA Ulises GáZQUEZ José L. VELA Alberto 《物理化学学报》 SCIE CAS CSCD 北大核心 2018年第6期692-698,共7页
A global and local charge transfer partitioning model,based on the cornerstone theory developed by Robert G.Parr and Robert G.Pearson,which introduces two charge transfer channels(one for accepting electrons(electroph... A global and local charge transfer partitioning model,based on the cornerstone theory developed by Robert G.Parr and Robert G.Pearson,which introduces two charge transfer channels(one for accepting electrons(electrophilic) and another for donating(nucleophilic)),is applied to the reaction of a set of indoles with 4,6-dinitrobenzofuroxan.The global analysis indicates that the prevalent electron transfer mechanism in the reaction is a nucleophilic one on the indoles,i.e.,the indoles under consideration transfer electrons to 4,6-dinitrobenzofuroxan.Evaluating the reactivity descriptorswith exchange-correlation functionals including exact exchange(global hybrids) yields slightly better correlations than those obtained with generalized gradient-approximated functionals;however,the trends are preserved.Comparing the trend obtained with the number of electrons donated by the indoles,and predicted by the partitioning model,with that observed experimentally based on the measured rate constants,we propose that the number of electrons transferred through this channel can be used as a nucleophilicity scale to order the reactivity of indoles towards 4,6-dinitrobenzofuroxan.This approach to obtain reactivity scales has the advantage of depending on the intrinsic properties of the two reacting species;therefore,it opens the possibility that the same group of molecules may show different reactivity trends depending on the species with which they are reacting.The local model allows systematic incorporation of the reactive atoms based on the their decreasing condensed Fukui functions,and the correlations obtained by increasing the number of reactive atoms participating in the local analysis of the transferred nucleophilic charge improve,reaching an optimal correlation,which in the present case indicates keeping three atoms from the indoles and two from 4,6-dinitrobenzofuroxan.The atoms selected by this procedure provide valuable information about the local reactivity of the indoles.We further show that this information about the most reactive atoms on each reactant,combined with the spatial distribution of the nucleophilic and electrophilic Fukui functions of both reactants,allows one to propose non-trivial candidates of starting geometries for the search of the transition state structures present in these reactions. 展开更多
关键词 Chemical REACTIVITY CONCEPTUAL DFT Charge transfer NUCLEOPHILICITY indoles Transition state prediction
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Facile synthesis of indoles by K2CO3 catalyzed cyclization reaction of 2-ethynylanilines in water 被引量:1
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作者 Zhi Chen Xiao-Xiao Shi +4 位作者 Dong-Qin Ge Zhen-Zhen Jiang Qi-Qi Jin Hua-Jiang Jiang Jia-Shou Wu 《Chinese Chemical Letters》 SCIE CAS CSCD 2017年第2期231-234,共4页
The cyclization reaction of 2-ethynyl-N-sulfonylanilides proceeded efficiently in water with the presence of a catalytic amount of K2CO3 under transition metal-free condition to give indoles in high yields.The recover... The cyclization reaction of 2-ethynyl-N-sulfonylanilides proceeded efficiently in water with the presence of a catalytic amount of K2CO3 under transition metal-free condition to give indoles in high yields.The recovery and reusability of the present catalytic system were investigated. 展开更多
关键词 2-Ethynylanilines Cyclization reaction indoles Water Potassium carbonate
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Convenient synthesis of bis(indolyl)alkanes by dithiocarbohydrazone Schiff base/Zn(ClO_4 )_2 6H_2 O catalyzed Friedel–Crafts reaction of indoles with imines 被引量:1
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作者 Yong-Hai Hui Yong-Cheng Chen +1 位作者 Hai-Wei Gong Zheng-Feng Xie 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第1期163-165,共3页
A new, convenient and excellent yield procedure for the preparation of bis(indolyl)methanes (BIMs) by Friedel-Crafts reaction of indoles with imines in the presence of dithiocarbohydrazone Schiff base/ Zn(CIO4)2... A new, convenient and excellent yield procedure for the preparation of bis(indolyl)methanes (BIMs) by Friedel-Crafts reaction of indoles with imines in the presence of dithiocarbohydrazone Schiff base/ Zn(CIO4)2.6H2O as a highly stable, effective and readily available catalyst is described. Moderate to good yields (up to 99% yield) were obtained with both substrates for imine derivatives. This procedure is simple, practical and economic. 展开更多
关键词 Friedel-Crafts reaction indoles Imines BIMs
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Synthesis and preliminary cytotoxic evaluation of substituted indoles as potential anticancer agents
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作者 Chang Qing Shi Zhang Qin Liu +1 位作者 Wen Qing Lin Yuan Wei Chen 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第8期899-901,共3页
A variety of indole derivatives were designed, synthesized and preliminarily evaluated for their in vitro cytotoxic activity in the A431 and H460 cell lines. All the compounds examined conferred unusual potency in a t... A variety of indole derivatives were designed, synthesized and preliminarily evaluated for their in vitro cytotoxic activity in the A431 and H460 cell lines. All the compounds examined conferred unusual potency in a tumor cell cytotoxicity assay. The findings showed the indole derivatives would be a promising candidate for the development of new anticancer agents. 展开更多
关键词 indoles SYNTHESIS Kinesin spindle protein inhibitor CYTOTOXICITY Cancer treatment
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Palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids:Construction of carbonyl-containing indolo[2,1-a]isoquinoline derivatives
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作者 Siqi Wang Jian-Shu Wang +1 位作者 Jun Ying Xiao-Feng Wu 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第5期259-262,共4页
A novel palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids is described,which provides a facile approach to access indolo[2,1-a]isoquinoline scaffolds.This metho... A novel palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids is described,which provides a facile approach to access indolo[2,1-a]isoquinoline scaffolds.This method employs benzene-1,3,5-triyl triformate(TFBen)as the CO surrogate for the incorporation of a carbonyl group into indolo[2,1-a]isoquinoline scaffolds,and a variety of carbonyl-containing indolo[2,1-a]isoquinoline derivatives are prepared in good yields. 展开更多
关键词 Carbonylative cyclization Palladium catalysis Indolo[2 1-a]isoquinolines Alkene-tethered indoles PHENOLS Arylboronic acids
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BF_3-promoted annulation of azonaphthalenes and ynamides for synthesis of benzo[e]indoles
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作者 Changwei Chen Sunliang Cui 《Chinese Chemical Letters》 SCIE CAS CSCD 2021年第1期421-424,共4页
A novel BF_(3)-promoted [3+2] annulation of azonaphthalenes and ynamides is described.This protocol provides a modular and efficient entry to functionalized amino benzo[e]indole derivatives smoothly.
关键词 Azonaphthalenes YNAMIDES ANNULATION Benzo[e]indoles
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Regioselective 2-alkylation of indoles withα-bromo esters catalyzed by Pd/P,P=O system
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作者 Wei Tian Bowen Li +1 位作者 Duanshuai Tian Wenjun Tang 《Chinese Chemical Letters》 SCIE CAS CSCD 2022年第1期197-200,共4页
A palladium-catalyzed 2-alkylation of indoles withα-bromo esters is developed by employing a P,P=O ligand.The method features excellent regioselectivities,mild reaction conditions,and good functional group compatibil... A palladium-catalyzed 2-alkylation of indoles withα-bromo esters is developed by employing a P,P=O ligand.The method features excellent regioselectivities,mild reaction conditions,and good functional group compatibility.The employment of the P,P=O ligand as well as 4 A molecular sieves were crucial for the success of the transformation.Mechanistic studies indicate the reaction proceed through a radical pathway. 展开更多
关键词 CROSS-COUPLING ALKYLATION indoles Palladium catalysis
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HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones from indoles and isatins
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作者 Xiaohan Yuan Shuai Wang +2 位作者 Jialing Cheng Bin Yu Hong-Min Liu 《Chinese Chemical Letters》 SCIE CAS CSCD 2020年第9期2465-2468,共4页
The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are d... The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are described.This protocol shows well tolerance of different functional groups and features mild reaction conditions such as short reaction time(~1 h),no usage of catalyst,easy operation and product isolation.Of particular intere st is the formation of two C-C bonds and one all-carbon quaternary center.This protocol could serve as an alternative strategy to synthesize biologically important 3,3-di(indolyl)indolin-2-ones for biological testing. 展开更多
关键词 indoles ISATINS HFIP Catalyst-free synthesis 3 3-Di(indoly)indolin-2-ones
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Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles
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作者 Yu-Hang Miao Zheng-Xu Zhang +6 位作者 Xu-Yi Huang Yuan-Zhao Hua Shi-Kun Jia Xiao Xiao Min-Can Wang Li-Ping Xu Guang-Jian Mei 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第4期357-362,共6页
Due to the high electrophilic nature of azo-dienophiles, azo-Diels–Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the “click reaction”. This spontaneity causes strong backgr... Due to the high electrophilic nature of azo-dienophiles, azo-Diels–Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the “click reaction”. This spontaneity causes strong background reaction and poses a daunting challenge to chemists for developing the catalytic asymmetric version. Reported herein is the first catalytic asymmetric dearomative azo-Diels–Alder reaction between2-vinylindoles and triazoledione. This protocol makes use of the high energy barrier of dearomatization to avert the strong background reaction of azo-Diels–Alder reaction, allowing the implementation of the projected reaction at ambient temperature. Density functional theory calculations have been performed to gain insights into the reaction mechanism and the origins of the enantioselectivity. By using this method,a variety of tetracyclic indole derivatives have been readily prepared in good to excellent yields and with excellent diastereo-and enantio–selectivities(33 examples, up to 97% yield and >99% ee, >20:1 dr). 展开更多
关键词 Catalytic asymmetric dearomatization Azo-Diels–Alder reaction 2-Vinylindoles Chiral phosphoric acid Tetracyclic indole derivatives
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Phosphotungstic Acid Catalyzed Conjugate Addition of Indoles with α,β-Enones
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作者 Wenpin Wang Zhengfeng Xie +1 位作者 Ye Xing Fangming Liu 《Journal of Chemistry and Chemical Engineering》 2010年第8期21-25,共5页
A new facile, efficient and very mild entry to the synthesis of 3-(1H-indol-3-yl)-1, 3-diarylpropan-l-ones is presented. The procedure utilizes phosphotungstic acid (5 mol%) as a catalyst for the Michael addition ... A new facile, efficient and very mild entry to the synthesis of 3-(1H-indol-3-yl)-1, 3-diarylpropan-l-ones is presented. The procedure utilizes phosphotungstic acid (5 mol%) as a catalyst for the Michael addition of indole to α,β-unsaturated ketones in good yield in acetonitrile as solvent. 展开更多
关键词 Phosphotungstic acid indoles α β-enones Michael ddition reaction catalysis.
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Conjugate Addition of Indoles to <i>α,β</i>-Unsaturated Ketones Using Bismuth (III) Bromide
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作者 Tyler J. Rauwolf Zhijia Geng +4 位作者 Zachary P. Kinney Jared L. Renfroe Jack H. Roireau Lauren T. Yep Ram S. Mohan 《Green and Sustainable Chemistry》 2019年第3期79-84,共6页
An efficient method for the conjugate addition of indoles to a variety of chalcones using BiBr3 in ethanol (190 proof) is reported. Products are isolated by a simple procedure that avoids an aqueous work up and extens... An efficient method for the conjugate addition of indoles to a variety of chalcones using BiBr3 in ethanol (190 proof) is reported. Products are isolated by a simple procedure that avoids an aqueous work up and extensive chromatography, thus minimizing waste. Bismuth (III) compounds are especially attractive from a green chemistry perspective because they are remarkably nontoxic, non-corrosive and relatively inexpensive. 展开更多
关键词 BISMUTH BISMUTH BROMIDE CONJUGATE Addition Green Chemistry indoles
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A new approach for one-pot,green synthesis of new polycyclic indoles in aqueous solution
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作者 Mohsen Ameri Alireza Asghari +1 位作者 Ali Amoozadeh Mohammad Bakherad 《Chinese Chemical Letters》 SCIE CAS CSCD 2017年第5期1031-1034,共4页
Electro-oxidation of phenylamine derivatives(1a and 1b) have been studied in the presence of pyrazolidine-3,5-dione(3) as a nucleophile in phosphate buffer solution mixed with ethanol,using voltammetric and spectr... Electro-oxidation of phenylamine derivatives(1a and 1b) have been studied in the presence of pyrazolidine-3,5-dione(3) as a nucleophile in phosphate buffer solution mixed with ethanol,using voltammetric and spectroscopic techniques.The obtained results indicated that the oxidized form of phenylamines(2a and 2b) participate in Michael addition type reactions with pyrazolidine-3,5-dione(3) and via ECECCCCC mechanisms convert to the corresponding new polycyclic indoles(12a and 12b).In the present study,new polycyclic indole derivatives were synthesized with good yields and high purity using a facile,one-pot and environmentally friendly electrochemical method,without any chemical catalysts,toxic solvents and hard conditions. 展开更多
关键词 Electro-oxidation Phenylamine Polycyclic indoles Environmentally friendly ECECCCCC mechanism
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Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by Cu(Ⅱ)-imine complex 被引量:3
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作者 Ning Ning Wan Yong Lei Yang +2 位作者 Wen Ping Wang Zheng Feng Xie Ji De Wang 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第10期1155-1158,共4页
A series of new ligands L_1-L_7 were readily prepared in one step.Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a novel Cu(Ⅱ)-L complex has been developed.The remarkable advantages of this rea... A series of new ligands L_1-L_7 were readily prepared in one step.Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a novel Cu(Ⅱ)-L complex has been developed.The remarkable advantages of this reaction are mild reaction conditions,simple workup procedure,high yields of products and the use of ethanol as a green solvent. 展开更多
关键词 Friedel-Crafts alkylation INDOLE NITROALKENE Copper IMINE
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Pyridinium tribromide catalyzed condensation of indoles and aldehydes to form bisindolylalkanes 被引量:2
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作者 Qin Yang Zheng Lan Yin +1 位作者 Ban Lai Ouyang YiYuan Peng 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第5期515-518,共4页
An efficient synthetic method for bis(indol-3-yl)alkane derivatives has been developed.In the presence of 5 mol%of pyridinium tribromide(PTB),the condensation of indoles and aldehydes proceeded smoothly under mild... An efficient synthetic method for bis(indol-3-yl)alkane derivatives has been developed.In the presence of 5 mol%of pyridinium tribromide(PTB),the condensation of indoles and aldehydes proceeded smoothly under mild conditions,giving rise to the corresponding bis(indol-3-yl)alkanes in good to excellent yields. 展开更多
关键词 Pyridinium tribromide INDOLE ALDEHYDE Bis(indol-3-yl)alkane
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