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cascade reaction of 3-formylchromones:Highly selective synthesis of 4-oxo-3-(1H-pyrrol-3-yl)-4H-chromenes

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Green Synthesis and Catalysis 2024年第2期5卷 94-101页

作者： Ying Lv Li Chen Xinghan Yun Kun Li Shengjiao Yan Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University) Ministry of EducationSchool of Chemical Science and TechnologyYunnan UniversityKunming 650091China

A novel method for the preparation of highly functionalized 4-oxo-3-(1H-pyrrol-3-yl)-4H-chromenes(OPCMs)from 3-formylchromones andα-isocyanoacetates via an unprecedented three-component[1+1+3]cycloaddition reaction in one pot was *** three-component cascade reaction was enabled by refluxing a mixture of the substrates in 1,4-dioxane in the presence of Ag_(2)CO_(3) as a Lewis acid *** a result,a series of functionalized pyrroles(OPCMs,3),was prepared regioselectively and in high yields(80%-88%)through the formation of three *** protocol can be used in the synthesis of OPCMs rather than through conventional,multi-step reactions and is suitable for both combinatorial and parallel syntheses of pyrroles.

关键词： 4-Oxo-3-(1H-pyrrol-3-yl)-4H-chromenes Three-component cascade reaction [1+1+3]cycloaddition 3-Formylchromones

4-Dimethylaminopyridine-catalyzed cascade reaction for Efficient Synthesis of Naphthofurans

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Chemical Research in Chinese Universities 2016年第1期32卷 62-67页

作者： FAN Chenli HE Xinwei LIAO Kaisheng WANG Cui'e SHANG Yongjia Department of Material Engineering Wuhu Institute of Technology Wuhu 241003 P. R. China Key Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Molecule-based Materials College of Chemistry and Materials Science Anhui Normal University Wuhu 241000 P. R. China

A convenient and efficient method was developed for the synthesis of naphtho[2,1-blfurans via 4-dimethylaminopyridine（DMAP）-catalyzed cascade reaction of 2-hydroxy-l-naphthaldehydes and a-halogenated ketones in moderate to good yields in the presence of Na2CO3 at 80 ~C for 6 h. The mechanism for this process was briefly discussed with a tentative catalytic cycle proposed. Moreover, this method features organocatalysts and high step-economy, which makes it practical and attractive.

关键词： 4-Dimethylaminopyridine a-Halogenated ketone cascade reaction Naphthofuran Organocatalysis

NIR-II driven plasmon-enhanced cascade reaction for tumor microenvironment-regulated catalytic therapy based on bio-breakable Au-Ag nanozyme

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Nano Research 2020年第8期13卷 2118-2129页

作者： Min Xu Qianglan Lu Yiling Song Lifang Yang Chuchu Ren Wen Li Ping Liu Yule Wang Yan Zhu Nan Li Tianjin Key Laboratory of Drug Delivery&High-Efficiency School of Pharmaceutical Science and TechnologyTianjin UniversityTianjin300072China Tianjin State Key Laboratory of Modern Chinese Medicine Tianjin University of Traditional Chinese MedicineTianjin301617China Research and Development Center of TCM Tianjin International Joint Academy of Biotechnology and MedicineTianjin300457China

Emerging nanozymes with natural enzyme-mimicking catalytic activities have inspired extensive research interests due to their high stability,low cost,and simple preparation,especially in the field of catalytic tumor ***,bio-breakable nanozymes based on glucose-oxidase(GOx)-loaded biomimetic Au–Ag hollow nanotriangles(Au–Ag–GOx HTNs)are designed,and they trigger an near-infrared(NIR)-II-driven plasmon-enhanced cascade catalytic reaction through regulating tumor microenvironment(TME)for highly efficient tumor ***,GOx can effectively trigger the generation of gluconic acid(H+)and hydrogen peroxide(H2O2),thus depleting nutrients in the tumor cells as well as modifying TME to provide conditions for subsequent peroxidase(POD)-like ***,NIR-II induced surface plasmon resonance can induce hot electrons to enhance the catalytic activity of Au–Ag–GOx HTNs,eventually boosting the generation of hydroxyl radicals(•OH).Interestingly,the generated H2O2 and H+can simultaneously induce the degradation of Ag nanoprisms to break the intact triangle nanostructure,thus promoting the excretion of Au–Ag–GOx HTNs to avoid the potential risks of drug ***,the NIR-II driven plasmon-enhanced catalytic mechanism of this bio-breakable nanozyme provides a promising approach for the development of nanozymes in tumor therapy.

关键词： near-infrared(NIR)-II driven plasmon-enhanced catalysis Au-Ag hollow nan otria ngles bio-breakable cascade reaction

Temperature-controlled cascade reaction of Phloroglucinoltribenzyl Ether Promoted by Trifluoroacetic Anhydride and Trifluoroacetic Acid

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Chemical Research in Chinese Universities 2016年第3期32卷 378-379页

作者： LI Bonan DU Lijun LI Jianqi Novel Technology Center of Pharmaceutical Chemistry Shanghai Institute of Pharmaceutical Industry Shanghai 201203 P R. China School of Life Science Tsinghua University Beijing 100084 P R. China

We report the first trifluoroacetic anhydride- and trifluoroacetic acid-promoted cascade reaction with phtoroglucinoltribenzyl ether and carboxylic acid as starting materials. By simply varying the temperature of systems containing the same starting materials, different products were produced in high yields. A three-step consecutive reaction process was also proposed.

关键词： cascade reaction Phloroglucinol Trifluoroacetic anhydride(TFAA) Trifluoroacetic acid(TFA)

Multisubstituted pyrazole synthesis via[3+2]cycloaddition/rearrangement/N-H insertion cascade reaction of α-diazoesters and ynones

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Chinese Chemical Letters 2021年第1期32卷 132-135页

作者： Peng Zhao Zi Zeng Xiaoming Feng Xiaohua Liu Key Laboratory of Green Chemistry&Technology Ministry of EducationCollege of ChemistrySichuan UniversityChengdu 610064China

The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)_(3) as the catalyst are described.A series of 4-substituted pyrazoles were obtained via [3+2] cycloaddition,1,5-ester shift,1,3-H shift,and N-H insertion *** labelling experiments,kinetic studies and control experiments were carried out for the rationalization of the mechanism.

关键词： Pyrazole cascade reaction α-Diazoester Ynone Al(OTf)_(3)

Positional assembly of multi-enzyme cascade reaction in polyelectrolyte doped microcapsule through electrospray and layer-by-layer assembly

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Synthetic and Systems Biotechnology 2020年第3期5卷 206-213页

作者： Shiyi Che Jie Wang Xiaoyuan Ji Zhiguo Su Shaomin Wang Songping Zhang State Key Laboratory of Biochemical Engineering Institute of Process EngineeringChinese Academy of SciencesBeijing100190China University of Chinese Academy of Sciences No.19 Yuquan RoadShijingshan DistrictBeijing100049China College of Chemistry Zhengzhou UniversityZhengzhou450001China

Polyelectrolyte-doped microcapsules(PDM)was fabricated by coaxial electrospray of a mixture of glycerol and water containing 10 mg/mL cationic polyelectrolyte poly(allylamine hydrochloride)(PAH)fed as the core phase solution,and a N,N-dimethylacetylamide solution of 10 wt%polyurethane fed as the shell phase *** system involving Candida Antarctica lipase B(CALB),glucose oxidase(GOD),and horseradish peroxidase(HRP)for cascade reaction was assembled in the PDM at three different places,namely,surface,shell,and *** of enzyme inside aqueous lumen of the PDM was realized by in situ encapsulation through adding the enzyme in the core-phase solution for coaxial *** ion-pairing of enzyme with cationic surfactant CTAB,an organic soluble enzyme-CTAB complex was prepared,so that in situ embedding of enzyme in the shell of the PDM was realized by adding it into the shell phase *** attachment of enzymes was achieved by layer-by-layer(LbL)technology,which is based on the ion-exchange interactions between oppositely charged enzymes and PAH that was doped in *** enzyme-decorated microcapsule was then studied as a microbioreactor,in which 1-Oxododecyla-α-glucopyranoside was converted by CALB to glucose,which was oxidised by GOD to gluconolactone in a second *** hydrogen peroxide produced was then used by HRP to oxidize ABTS to form coloured radical cation ABTS•+for activity *** successful fabrication of the PDM and precise localization of enzymes in the PDM by different strategies were fully *** varying the immobilization strategy,totally six PDM bioreactors with three enzymes precisely positional assembled in different strategies were constructed and their activities for the cascade reaction were investigated and *** PDM micro-bioreactor prepared by novel electrospray technologies provide a smart platform for positional assembly of multi-enzyme cascade reaction in a precise and well-controlle

关键词： Coaxial electrospray Microcapsule Multi-enzyme cascade reaction Positional assembly Layer-by-layer assembly

NHC-catalysed retro-aldol/aldol cascade reaction enabling solvent-controlled stereodivergent synthesis of spirooxindoles

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Chinese Chemical Letters 2021年第8期32卷 2567-2571页

作者： Haijun Leng Qian Zhao Qing Mao Shuaijiang Liu Menglan Luo Rui Qin Wei Huang Gu Zhan State Key Laboratory of Southwestern Chinese Medicine Resources School of Pharmacy and School of Basic Medical SciencesChengdu University of Traditional Chinese MedicineChengdu 611137China Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province Sichuan Industrial Institute of AntibioticsSchool of PharmacyChengdu UniversityChengdu 610052China

An N-heterocyclic carbene(NHC)-catalysed retro-aldol/aldol cascade reaction of spirooxindole-basedβ-hydroxyaldehyde has been *** ring opening-closure process enables the diastereodivergent synthesis of spirocyclopentaneoxindole products with four consecutive stereocenters by simply changing the reaction solvents(THF or DCE).The Michael/aldol/retro-aldol/aldol sequential protocol allows the diastereodivergent synthesis of spirocyclopentaneoxindoles from 3-substituted oxindole andα,β-unsaturated aldehyde under the relay catalysis of a chiral secondary amine and an NHC ***,four stereoisomers of the product can be selectively provided by using different combinations of a chiral secondary amine and a solvent.

关键词： Asymmetric synthesis Solvent-controlled diastereodivergence Retro-aldol/aldol cascade reaction Spirooxindole N-Heterocyclic carbene catalysis

Highly selective synthesis of functionalized morphan derivatives through a multi-component cascade reaction of 3-formylchromones, 2-naphthols, and enaminones

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Green Synthesis and Catalysis 2023年第4期4卷 321-329页

作者： Xinling Cao Yinggang Duan Kaihong Lv Zihan Lu Yihua Chen Shengjiao Yan Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University) Ministry of EducationSchool of Chemical Science and TechnologyYunnan UniversityKunming 650091China

A novel protocol for the preparation of highly functionalized 2-azabicyclo[3.3.1]nonane(morphan)derivatives via a multicomponent cascade reaction,involving 3-formylchromones,2-naphthols,and enaminones in the ionic liquid[BMIM]PF6 as the solvent and promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU),was developed,which involved the cleavage of one C–O bond and formation of four bonds(1 C–O,1 C–N,and 2 C–C bonds).As a result,a series of morphan derivatives were produced through a cascade reaction,including a sequence of 1,2-addition,enol-keto tautomerization,Michael addition,dehydration,another Michael addition,imine-enamine tautomerization,and N-alkylation reactions,which were accompanied by a ring-opening *** protocol was suitable for combinatorial and parallel syntheses of natural product-like morphan compounds in a one-pot reaction rather than through tedious multi-step reactions.

关键词： Morphan derivatives Site-selective synthesis cascade reaction Enaminones 3-Formylchromones

Multicomponent cascade reaction of 3-formylchromones:Highly regioselective synthesis of functionalized pyridin-2(1H)-ones

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Green Synthesis and Catalysis 2023年第3期4卷 231-239页

作者： Xinghan Yun Li Chen Ying Lv Zihan Lu Kun Huang Shengjiao Yan Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University) Ministry of EducationSchool of Chemical Science and TechnologyYunnan UniversityKunming650091China

A novel protocol was developed for the construction of highly functionalized pyridin-2(1H)-ones from 3-formylchromones,ethyl 2-(pyridin-2-yl)acetate derivatives and amines via a complex multicomponent cascade reaction involving targeted duplicated ring-opening and duplicated cyclization reactions which form skeleton-reorganized target compounds.A series of pyridin-2(1H)-ones were produced by this reaction accompanied by the formation of three bonds(one C–N and two C–C bonds)and the cleavage of one bond in one *** protocol can be used in combinatorial and parallel syntheses of various pyridin-2(1H)-ones with potent biological *** advantages of this approach include simple and practical operation(multicomponent one-pot),high yields(up to 91%),and products with potential biological activity.

关键词： Pyridin-2(1H)-ones cascade reaction Selective synthesis 3-Formylchromones