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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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Chinese Chemical Letters 2020年第9期31卷 2465-2468页

作者： Xiaohan Yuan Shuai Wang Jialing Cheng Bin Yu Hong-Min Liu School of Pharmaceutical Sciences Zhengzhou UniversityZhengzhou 450001China Gordon Center for Medical Imaging Massachusetts General Hospital and Harvard Medical SchoolBostonMA 02129United States State Key Laboratory of Natural Medicines China Pharmaceutical UniversityNanjing 210009China

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.

关键词： Indoles Isatins HFIP Catalyst-free synthesis 3,3-Di(indoly)indolin-2-ones

Synthesis of 2,3-Fused Indoline Aminals via 4+2 Cycloaddition of NH-free Benzazetidines with Indoles

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Chinese Journal of Chemistry 2019年第2期37卷 119-125页

作者： Zibo Bai Huarong Tong Hao Wang Gong Chen Gang He State Key Laboratory and Institute of Elemento-Organic Chemistry College of ChemistryNankai UniversityTianjin 300071China Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) Tianjin 300071China

Summary of main observation and conclusion A 4+2 cycloaddition reaction of NH-free benzazetidines with Indoles under the catalysis of camphorsulfonic acid was developed. This method shows a broad substrate scope of benzazetidines and Indoles, and offers a convenient method for stereoselective synthesis of various cis-2,3-fused indoline aminals. Preliminary mechanistic studies suggest the reaction proceed via a stepwise pathway featuring an electrophilic attack on the benzylic carbon of benzazetidine.

关键词： Synthesis of 2,3-Fused Indoline Aminals 4+2 Cycloaddition of NH-free Benzazetidines with Indoles

Reactivity of Indoles through the Eyes of a Charge-Transfer Partitioning Analysis

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物理化学学报 2018年第6期34卷 692-698页

作者： OROZCO-VALENCIA Ulises GáZQUEZ José L. VELA Alberto Departamento de Quimica Centro de Investigacion y de Estudios Avanzados Av. Instituto Politecnico Nacional 2508 Colonia San Pedro Zacatenco Ciudad de Mexico 07360 Mexico. Departamento de Quimica Universidad Autonoma Metropolitana-Iztapalapa

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 m

关键词： Chemical reactivity Conceptual DFT Charge transfer Nucleophilicity Indoles Transition state prediction

A convenient one-pot three component synthesis of 3-aminoalkylated Indoles catalyzed by 3-chlorophenylboronic acid

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Chinese Chemical Letters 2013年第5期24卷 422-424页

作者： Santosh V.Goswami Prashant.B.Thorat Vijay N.Kadam Sachin A.Khiste Sudhakar R.Bhusare Department of Chemistry Dnyanopasak College

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.

关键词： 3-Aminoalkylaed Indoles 3-Chlorophenylboronic acid Aromatic aldehyde N-Methylaniline Indoles

Metal, iodine and oxidant-free electrosynthesis of substituted Indoles from 1-(2-aminophenyl)alcohols

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Green Synthesis and Catalysis

Green Synthesis and Catalysis 2023年第4期4卷 311-315页

作者： Chengcheng Yuan Xiangxing Huang Yi Lu Zheng Fang Chengkou Liu Beining Chen Kai Guo College of Biotechnology and Pharmaceutical Engineering Nanjing Tech UniversityNanjing 211816China Department of Chemistry University of SheffieldSheffield S37HFUK State Key Laboratory of Materials-Oriented Chemical Engineering Nanjing Tech UniversityNanjing 211816China

A green and straightforward electrosynthesis of substituted Indoles has been developed through dehydration and intramolecular dehydrogenative C–N bond-forming radical cross-coupling from 1-(2-aminophenyl)alcohols under metal,iodine and oxidant-free conditions.This electrochemical indole synthesis strategy has an excellent functional group,water and air tolerance.And,a possible cyclization process was proposed based on the radicaltrapping,intermediate verification,cyclic voltammetry,EPR and control experiments.

关键词： Electrosynthesis Metal Iodine and oxidant-free C-N coupling Indoles N-centered radicals

Conjugate Addition of Indoles to α, β-Unsaturated Ketones （Chalcones） Catalyzed by KHSO4 under Ultrasonic Conditions

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Chinese Journal of Chemistry 2007年第12期25卷 1777-1780页

作者：曾晓飞纪顺俊沈舒苏 Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry and Chemical Engineering Suzhou University Suzhou Jiangsu 215123 China

Conjugate addition of Indoles to a variety of α,β-unsaturated ketones （chalcones） mediated by a catalytic amount of KHSO4 at room temperature under ultrasonic conditions to afford the corresponding Michael adducts... 详细信息

关键词： KHSO4 Indoles α,β-unsaturated ketones conjugate addition reaction

Photo-Induced Direct C-C/C-N Bond Formation:Synthesis of Indoles via EDA Complexes

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Photo-Induced Direct C-C/C-N Bond Formation:Synthesis of Ind...

Nickel(Ⅱ)-catalyzed enantioselective Friedel-Crafts alkylation of Indoles with β-CF3-β-(3-indolyl)nitroalkenes

中国化学会·第十六届全国有机合成化学学术研讨会

作者： Kailiang Tao 郭维 Lvyin Zheng Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province Gannan Normal University 赣南师范大学

Electron donor-acceptor complexes have known wide applications for the construction of useful organic products by photochemical transformations in recent years.Driven by light irradiation,the electron transfer within EDA complex plays an important role in promoting the generation of active radical species,which further facilitates the subsequent transformation. Based on our previous work,we herein explored in-situ generated EDA complexes derived from secondary arylamines and alkynes.The unique direct C-C/C-N bond foramation can be promoted by the photochemical activity of EDA complex to afford Indoles without using of any metals,oxidants and external photocatalysts.The in-situ generated EDA complex derived from arylamines with alkynes was characterized by UV-vis absorption spectrometry and NMR titration experiments.Considering the advantages of the combination of EDA complexes and visible light irradiation(convenient operation,simple conditions and environmentally friendly),this approach exhibits potential applications in organic synthesis and pharmaceutical chemistry.

关键词： Indoles photo-driven EDA complexes

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Nickel(Ⅱ)-catalyzed enantioselective Friedel-Crafts alkylat...

[60]FulleroIndoles: One-Pot Transition-Metal-Free Synthesis via KOtBu-Promoted C3 Selective Coupling Reaction of Indoles and [60]Fullerene

中国化学会·第十六届全国有机合成化学学术研讨会

作者：朱文静 Jun-Fang Gong Mao-Ping Song 郑州大学 College of Chemistry Henan Key Laboratory of Chemical Biology and Organic ChemistryZhengzhou University

The bis(3-indolyl)methanes(BIMs) are very important compounds whichpossess a broad range of biological and pharmacological activities.For example,they have the functions of inhibiting cancer cell growth,antiinflammatory,antifungal.They are also utilized as tranquilizers and dietary supplement for humans. In the past decades,lots of synthetic methods of achiral BIMs have been reported.In contrast,the enantioselective synthesis of optically pure unsymmetrical BIMs has remained few.And in most cases thechiral BIMs were prepared by chiral phosphoric acid-catalyzed Friedel-Crafts alkylation of Indoles.2 In our previous work we demonstrated that the cobalt(Ⅱ)/(imidazoline-oxazoline) complex showed high levels of enantioselectivity inMichael addition of 2-acetyl azaarenes to β-CF-β-disubstituted nitroalkenes.3 Meanwhile,inspired by the literature results reported by Jia in 2013, we expected that the Ni(Ⅱ)/(imidazoline-oxazoline) complex could also promote theenantioselective Friedel-Crafts reaction of Indoles with β-CF-β-(3-indolyl)nitroalkenes.Pleasingly,the complex did perform well in the reactions,affording the products containing bis(indolyl)metiane framework and a trifluoromethylated all-carbon quaternary stereocenter in high yields and enantioselectivities.Moreover,both enantiomers of a given bis(indolyl)methane can be obtained after the N-protection group(PG) was removed.

关键词： asymmetric Friedel-Crafts alkylation Indoles β-CF3-β-（3-indolyl）nitroalkenes bis（3-indolyl）-methanes trifluoromethylated all-carbon quaternary stereocenter enantiomers

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[60]Fulleroindoles: One-Pot Transition-Metal-Free Synthesis ...