The development of the three-component catalytic system for constructing isoindolinones from simple feedstocks is both significant and challenging.In this study,a unique tartrate-linked dimeric samarium-antimonotungst...The development of the three-component catalytic system for constructing isoindolinones from simple feedstocks is both significant and challenging.In this study,a unique tartrate-linked dimeric samarium-antimonotungstate[Sm_(2)(H_(2)O)_(6)(tar)(Sb_(2)W_(21)O_(72))]_(2)^(20-)(Sm_(4)tar_(2),H_(4)tar=tartaric acid)was synthesized via a one-step method at room temperature using an acetate buffer solution.The dimeric polyanion of Sm4tar2shows a centrosymmetric structure with a parallelogram-like arrangement and comprises two enantiomeric{Sm_(2)(H_(2)O)_(6)(Sb_(2)W_(21)O_(72))}moieties connected by two enantiomeric tar ligands.Sm_(4)tar_(2)demonstrates efficient catalytic activity in the three-component reaction involving 2-acylbenzoic acids,primary amines,and phosphine oxides to form 3,3-disubstituted isoindolinones.The advantages of this catalytic system include simple feedstocks,green and reusable catalyst,and operational simplicity with water as the sole by-product.This finding enables an effective molecular fragment assembly strategy for synthesizing isoindolinone drug precursor skeletons.展开更多
A facile and environmentally friendly visible-light-induced three-component reaction of α-diazoesters,cyclic ethers and Na SCN to construct organic thiocyanates has been developed at room temperature. This reaction c...A facile and environmentally friendly visible-light-induced three-component reaction of α-diazoesters,cyclic ethers and Na SCN to construct organic thiocyanates has been developed at room temperature. This reaction could occur under photocatalyst-and additive-free conditions to afford a number of organic thiocyanates with moderate to good yield and favorable functional group tolerance.展开更多
A facile and metal-free visible-light-enabled three-component reaction of quinoxalin-2(1 H)-ones,alkenes and CF_(3)SO_(2)Na has been developed under air at room temperature.This photocatalytic tandem reaction using 4 ...A facile and metal-free visible-light-enabled three-component reaction of quinoxalin-2(1 H)-ones,alkenes and CF_(3)SO_(2)Na has been developed under air at room temperature.This photocatalytic tandem reaction using 4 CzIPN as the photocatalyst and air as the green oxidant,provides a mild and environmentally friendly approach to access a series of 3-trifluoroalkylated quinoxalin-2(1 H)-ones.展开更多
The functionalized spiro[indoline-3,40-pyrano[3,2-h]quinolines] were efficiently prepared in high yields from three-component reaction of 8-hydroxyquinoline, isatins and malononitrile or ethyl cyanoacetate in ethanol ...The functionalized spiro[indoline-3,40-pyrano[3,2-h]quinolines] were efficiently prepared in high yields from three-component reaction of 8-hydroxyquinoline, isatins and malononitrile or ethyl cyanoacetate in ethanol at room temperature for about 12 h in the presence of piperidine.展开更多
Potassium tert-butoxide has been found to be a highly efficient catalyst for one-pot,three-component reaction of aryl aldehydes, acetophenones,and thiols via Claisen-Schmidt/Michael addition reactions for the synthesi...Potassium tert-butoxide has been found to be a highly efficient catalyst for one-pot,three-component reaction of aryl aldehydes, acetophenones,and thiols via Claisen-Schmidt/Michael addition reactions for the synthesis of thia-Michael adducts in high yields. The reactions are best carried out in tert-butyl alcohol at room temperature.展开更多
A green Passerini three-component reaction of 2-（4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl）acetic acid with alkyl or aryl isocyanides and aldehydes was reported under aqueous conditions at 35 ℃ for 1 h, and21 indolone...A green Passerini three-component reaction of 2-（4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl）acetic acid with alkyl or aryl isocyanides and aldehydes was reported under aqueous conditions at 35 ℃ for 1 h, and21 indolone-N-amino acid derivatives were prepared in high yields of 42%–99%. Their structures were characterized by IR, ESI–MS, NMR and elemental analysis, and the possible mechanisms have been also proposed. The highly efficient and eco-friendly method provides a facile access to a library of indoloneN-amino acid derivatives for future research on bioactivity screening.展开更多
A simple and metal-free method has been developed for the construction of quinoline-2,4-carboxylates under mild conditions via a molecular iodine-catalyzed three-component tandem reaction of arylamines, ethyl glyoxyla...A simple and metal-free method has been developed for the construction of quinoline-2,4-carboxylates under mild conditions via a molecular iodine-catalyzed three-component tandem reaction of arylamines, ethyl glyoxylate, and a-ketoesters. The present protocol provides a convenient and attractive approach to various quinoline-2,4-carboxylates in moderate to good yields with excellent functional group tolerance.展开更多
Three-component reaction of arylsulfonamides,dialkyl acetylenedicarboxylates,and ethyl chlorooxoacetate promoted by triphenylphosphine and triethylamine provides a sufficient route for the synthesis of dialkyl N-（ary...Three-component reaction of arylsulfonamides,dialkyl acetylenedicarboxylates,and ethyl chlorooxoacetate promoted by triphenylphosphine and triethylamine provides a sufficient route for the synthesis of dialkyl N-（arylsulfonyl）-4-ethoxy-5-oxo-2,5-dihydro -1H-pyrolle-2,3-dicarboxylates in good yields.展开更多
In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo [1,2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proc...In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo [1,2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proceed smoothly with a high degree of functional group tolerance and provide the desired products in moderate to good yield.展开更多
The three-component reaction of aromatic aldehyde,malononitrile and aliphatic amine in a mixed solvent of methanol and water exhibited very interesting molecular diversity and gave the derivatives of polysubstituted N...The three-component reaction of aromatic aldehyde,malononitrile and aliphatic amine in a mixed solvent of methanol and water exhibited very interesting molecular diversity and gave the derivatives of polysubstituted N-methyldihydropyridines,2-dialkylaminopyridines and 2-methoxypyridines as main products according to the structure of aliphatic amines used.展开更多
A gold(Ⅰ)-catalyzed three-component reaction of β-nitrostyrenes with 1,3-dicarbonyl compounds and primary amines to form polysubstituted pyrroles has been developed at room temperature in ethanol.The key advantages ...A gold(Ⅰ)-catalyzed three-component reaction of β-nitrostyrenes with 1,3-dicarbonyl compounds and primary amines to form polysubstituted pyrroles has been developed at room temperature in ethanol.The key advantages of the three-component reaction are the mild reaction conditions and environmentally safer solvent.展开更多
The three-component reaction of triphenylphosphine,dialkyl but-2-ynedioate and arylidene pivaloylacetonitrile in dry methylene dichloride at room temperature resulted in unexpected densely substituted 1-（triphenyl-λ...The three-component reaction of triphenylphosphine,dialkyl but-2-ynedioate and arylidene pivaloylacetonitrile in dry methylene dichloride at room temperature resulted in unexpected densely substituted 1-（triphenyl-λ^5-phosphanylidene）ethyl）-2,3-dihydrofurans in satisfactory yields with high diastereoselectivity.The relative configuration of the 2,3-dihydrofurans was elucidated by determination of single crystal structures.展开更多
A new method was developed to diastereoselectively synthesize polysubstituted 1,2‐diamine compounds from the reaction of diazoesters with arylamines and diaryl imines by using the dioxazoline ligand L2‐ligated silve...A new method was developed to diastereoselectively synthesize polysubstituted 1,2‐diamine compounds from the reaction of diazoesters with arylamines and diaryl imines by using the dioxazoline ligand L2‐ligated silver catalyst.The Lewis acidity of the silver catalyst affected the different types of substrate diastereoselectivities;It also led to the formation of amine‐exchange side products.展开更多
A highly efficient three-component reaction has been developed for the synthesis of thiazolidinones involving the reaction of 2-amino-l-phenylethanone hydrochloride with an aromatic aldehyde and mercaptoacetic acid in...A highly efficient three-component reaction has been developed for the synthesis of thiazolidinones involving the reaction of 2-amino-l-phenylethanone hydrochloride with an aromatic aldehyde and mercaptoacetic acid in the presence of diisopropylethylamine in a single pot.Critically,this reaction exhibited excellent chemoselectivity,with the nitrogen atom of the 2-amino-l-phenylethanone component reacting selectively with the aromatic aldehyde to give the corresponding Schiff base.Nucleophilic attack at the carbon of the Schiff base by the sulfur atom of mercaptoacetic,followed by a cyclocondensation reaction between the nitrogen and the carboxylic acid moiety afforded the desired thiazolidinones,which were fully characterized by spectroscopic techniques.展开更多
A sequential one-pot two-step reaction for efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a]- quinoline derivatives in good yields has been successfully developed. The reaction included firstly Cu-c...A sequential one-pot two-step reaction for efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a]- quinoline derivatives in good yields has been successfully developed. The reaction included firstly Cu-catalyzed three-component reaction of isoquinoline （quinoline）, acetylenedicarboxylate and alkynylbenzene and then Pd-catalyzed intramolecular C（sp）-C（sp^2） coupling reaction of initially formed 1-alkenyl-2-alkynyl- 1,2-dihydroiso- quinoline （1,2-dihydroquinoline）.展开更多
In the presence of Cu（I） and triethyl amine, one-pot three-component reaction of fluoroalkanesulfonyl azides, alkynes and iminophosphoranes in CH2Cl2 at room temperature gave a novel class of fluorinated phosphorus ...In the presence of Cu（I） and triethyl amine, one-pot three-component reaction of fluoroalkanesulfonyl azides, alkynes and iminophosphoranes in CH2Cl2 at room temperature gave a novel class of fluorinated phosphorus amidines in good yields.展开更多
A strategy for the synthesis of benzisothiazoles by a three-component reaction was developed using elemental sulfur and ammonium as heteroatom components under transition metal-free conditions.The reaction is preferab...A strategy for the synthesis of benzisothiazoles by a three-component reaction was developed using elemental sulfur and ammonium as heteroatom components under transition metal-free conditions.The reaction is preferably based on pyridine or quinoline ring substrate,and good to excellent yields can be obtained.Notably,this reaction has been applied to the gram-scale synthesis of bioactive molecules.展开更多
A H_(4)SiW_(12)O_(40)-catalyzed three-component tandem reaction of 2-acylbenzoic acids,primary amines and phosphine oxides to form 3,3-disubstituted isoindolinones was developed.By employing A H_(4)SiW_(12)O_(40)as th...A H_(4)SiW_(12)O_(40)-catalyzed three-component tandem reaction of 2-acylbenzoic acids,primary amines and phosphine oxides to form 3,3-disubstituted isoindolinones was developed.By employing A H_(4)SiW_(12)O_(40)as the catalyst and dimethyl carbonate(DMC)as the solvent,a diverse range of 2-acylbenzoic acid derivatives and primary amines worked well to give the C3-phosphinoyl-functionalized 3,3-disubstituted isoindolinones with the yield range of 61%-87%.Advantages of this transformation include green catalyst and solvent,available starting materials,broad substrate scope,high efficiency and operational simplicity with water as the sole by-product.The strategy achieved an efficient and green molecular fragment assembly to access isoindolinones,which would provide opportunities for the synthesis of potential biologically active molecules in a green manner.展开更多
Cerium trichloride heptahydrate(CeCl_3·7H_2O) was found to be an efficient and recyclable catalyst for the three-component direct Mannich reaction of anilines and benzaldehydes with acetophenone.This protocol has...Cerium trichloride heptahydrate(CeCl_3·7H_2O) was found to be an efficient and recyclable catalyst for the three-component direct Mannich reaction of anilines and benzaldehydes with acetophenone.This protocol has advantages of high yield,no environmental pollution,mild condition,and simple work-up procedure.展开更多
基金financially supported by the National Natural Science Foundation of China(No.22301033)Jiangxi Provincial Natural Science Foundation(No.20232ACB213005 and 20212BAB213001)。
文摘The development of the three-component catalytic system for constructing isoindolinones from simple feedstocks is both significant and challenging.In this study,a unique tartrate-linked dimeric samarium-antimonotungstate[Sm_(2)(H_(2)O)_(6)(tar)(Sb_(2)W_(21)O_(72))]_(2)^(20-)(Sm_(4)tar_(2),H_(4)tar=tartaric acid)was synthesized via a one-step method at room temperature using an acetate buffer solution.The dimeric polyanion of Sm4tar2shows a centrosymmetric structure with a parallelogram-like arrangement and comprises two enantiomeric{Sm_(2)(H_(2)O)_(6)(Sb_(2)W_(21)O_(72))}moieties connected by two enantiomeric tar ligands.Sm_(4)tar_(2)demonstrates efficient catalytic activity in the three-component reaction involving 2-acylbenzoic acids,primary amines,and phosphine oxides to form 3,3-disubstituted isoindolinones.The advantages of this catalytic system include simple feedstocks,green and reusable catalyst,and operational simplicity with water as the sole by-product.This finding enables an effective molecular fragment assembly strategy for synthesizing isoindolinone drug precursor skeletons.
基金supported by the program of Science and Technology International Cooperation Project of Qinghai Province (No. 2022-HZ-813)the Youth Innovation and Technology Project of High School in Shandong Province (No. 2019KJC021)+1 种基金the Natural Science Foundation of Shandong Province (No. ZR2021MB065)the National Natural Science Foundation of China (No. 31900298)。
文摘A facile and environmentally friendly visible-light-induced three-component reaction of α-diazoesters,cyclic ethers and Na SCN to construct organic thiocyanates has been developed at room temperature. This reaction could occur under photocatalyst-and additive-free conditions to afford a number of organic thiocyanates with moderate to good yield and favorable functional group tolerance.
基金supported by Youth Innovation and Technology Project of Shandong Province(No.2019KJC021)the International Cooperation Project of Qinghai Province(No.2018-HZ-815)+2 种基金the Natural Science Foundation of Shandong Province(No.ZR2018MB009)the Qinghai key laboratory of Tibetan medicine research(No.2017-ZJ-Y11)CAS“Light of West China”Program 2018。
文摘A facile and metal-free visible-light-enabled three-component reaction of quinoxalin-2(1 H)-ones,alkenes and CF_(3)SO_(2)Na has been developed under air at room temperature.This photocatalytic tandem reaction using 4 CzIPN as the photocatalyst and air as the green oxidant,provides a mild and environmentally friendly approach to access a series of 3-trifluoroalkylated quinoxalin-2(1 H)-ones.
基金supported by the National Natural Science Foundation of China (Nos. 21172189, 21572196)the Priority Academic Program Development of Jiangsu Higher Education Institutions
文摘The functionalized spiro[indoline-3,40-pyrano[3,2-h]quinolines] were efficiently prepared in high yields from three-component reaction of 8-hydroxyquinoline, isatins and malononitrile or ethyl cyanoacetate in ethanol at room temperature for about 12 h in the presence of piperidine.
文摘Potassium tert-butoxide has been found to be a highly efficient catalyst for one-pot,three-component reaction of aryl aldehydes, acetophenones,and thiols via Claisen-Schmidt/Michael addition reactions for the synthesis of thia-Michael adducts in high yields. The reactions are best carried out in tert-butyl alcohol at room temperature.
基金the financial support by the Natural Science Foundation of China(No.21272136)Scientific Foundation from graduate school(2015PY089)Youth Talent Development Foundation of China Three Gorges University
文摘A green Passerini three-component reaction of 2-（4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl）acetic acid with alkyl or aryl isocyanides and aldehydes was reported under aqueous conditions at 35 ℃ for 1 h, and21 indolone-N-amino acid derivatives were prepared in high yields of 42%–99%. Their structures were characterized by IR, ESI–MS, NMR and elemental analysis, and the possible mechanisms have been also proposed. The highly efficient and eco-friendly method provides a facile access to a library of indoloneN-amino acid derivatives for future research on bioactivity screening.
基金supported by the Opening Project of Key Laboratory at Universities of Education Department of Xinjiang Uygur Autonomous Region (No. 2014YSHXZD01)
文摘A simple and metal-free method has been developed for the construction of quinoline-2,4-carboxylates under mild conditions via a molecular iodine-catalyzed three-component tandem reaction of arylamines, ethyl glyoxylate, and a-ketoesters. The present protocol provides a convenient and attractive approach to various quinoline-2,4-carboxylates in moderate to good yields with excellent functional group tolerance.
基金the financial support from the Research Council of Islamic Azad University,Mahshahr Branch
文摘Three-component reaction of arylsulfonamides,dialkyl acetylenedicarboxylates,and ethyl chlorooxoacetate promoted by triphenylphosphine and triethylamine provides a sufficient route for the synthesis of dialkyl N-（arylsulfonyl）-4-ethoxy-5-oxo-2,5-dihydro -1H-pyrolle-2,3-dicarboxylates in good yields.
基金supported by the National Natural Science Foundation of China(Nos.21072054,21572051,21602057)the Ministry of Education of China(No.213027A)the Scientific Research Fund of Hunan Provincial Education Department(No.15A109)
文摘In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo [1,2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proceed smoothly with a high degree of functional group tolerance and provide the desired products in moderate to good yield.
基金Supported by the National Natural Science Foundation of China(No.20972132)
文摘The three-component reaction of aromatic aldehyde,malononitrile and aliphatic amine in a mixed solvent of methanol and water exhibited very interesting molecular diversity and gave the derivatives of polysubstituted N-methyldihydropyridines,2-dialkylaminopyridines and 2-methoxypyridines as main products according to the structure of aliphatic amines used.
基金the Natural Science Foundation for Colleges and Universities of Jiangsu Province(No.17KJD150005)Science and Technology Project Funds of Lianyungang City(No.SH1627)+1 种基金Science and Technology Development Fund of Nanjing Medical University(Nos.2016NJMU011 and 2016NJMUZD021)Science and Technology Funds of Kangda College of Nanjing Medical University(Nos.KD2016GCCRCYJ01 and KD2016KYJJZD002)
文摘A gold(Ⅰ)-catalyzed three-component reaction of β-nitrostyrenes with 1,3-dicarbonyl compounds and primary amines to form polysubstituted pyrroles has been developed at room temperature in ethanol.The key advantages of the three-component reaction are the mild reaction conditions and environmentally safer solvent.
基金financially supported by the National Natural Science Foundation of China(No.21172190)the Priority Academic Program Development of Jiangsu Higher Education Institutions
文摘The three-component reaction of triphenylphosphine,dialkyl but-2-ynedioate and arylidene pivaloylacetonitrile in dry methylene dichloride at room temperature resulted in unexpected densely substituted 1-（triphenyl-λ^5-phosphanylidene）ethyl）-2,3-dihydrofurans in satisfactory yields with high diastereoselectivity.The relative configuration of the 2,3-dihydrofurans was elucidated by determination of single crystal structures.
基金the National Natural Science Foundation of China(21472237)~~
文摘A new method was developed to diastereoselectively synthesize polysubstituted 1,2‐diamine compounds from the reaction of diazoesters with arylamines and diaryl imines by using the dioxazoline ligand L2‐ligated silver catalyst.The Lewis acidity of the silver catalyst affected the different types of substrate diastereoselectivities;It also led to the formation of amine‐exchange side products.
基金supported by Special Assistance Programme SAP,University Grants Commission,New Delhi,India
文摘A highly efficient three-component reaction has been developed for the synthesis of thiazolidinones involving the reaction of 2-amino-l-phenylethanone hydrochloride with an aromatic aldehyde and mercaptoacetic acid in the presence of diisopropylethylamine in a single pot.Critically,this reaction exhibited excellent chemoselectivity,with the nitrogen atom of the 2-amino-l-phenylethanone component reacting selectively with the aromatic aldehyde to give the corresponding Schiff base.Nucleophilic attack at the carbon of the Schiff base by the sulfur atom of mercaptoacetic,followed by a cyclocondensation reaction between the nitrogen and the carboxylic acid moiety afforded the desired thiazolidinones,which were fully characterized by spectroscopic techniques.
文摘A sequential one-pot two-step reaction for efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a]- quinoline derivatives in good yields has been successfully developed. The reaction included firstly Cu-catalyzed three-component reaction of isoquinoline （quinoline）, acetylenedicarboxylate and alkynylbenzene and then Pd-catalyzed intramolecular C（sp）-C（sp^2） coupling reaction of initially formed 1-alkenyl-2-alkynyl- 1,2-dihydroiso- quinoline （1,2-dihydroquinoline）.
基金Project supported by the National Natural Science Foundation of China （Nos. 21032006, 20972178） and Shanghai Natural Science Council.
文摘In the presence of Cu（I） and triethyl amine, one-pot three-component reaction of fluoroalkanesulfonyl azides, alkynes and iminophosphoranes in CH2Cl2 at room temperature gave a novel class of fluorinated phosphorus amidines in good yields.
基金This work was supported by the Key Project Program of the Educational Department of Hunan Province(No.18A069)the Postgraduate Scientific Research Innovation Project of Hunan Province(No.QL20210148)+3 种基金the Scientific Research Foundation of Hunan Provincial Education Department(No.19C0522)the Scientific Research Foundation of Hunan Institute of Technology(No.2018HY011)the Project of Innovation Team of the Ministry of Education(No.IRT_17R90)Hunan 2011 Collaborative Innovation Center of Chemical Engineering&Technology with Environmental Benignity and Effective Resource Utilization.
文摘A strategy for the synthesis of benzisothiazoles by a three-component reaction was developed using elemental sulfur and ammonium as heteroatom components under transition metal-free conditions.The reaction is preferably based on pyridine or quinoline ring substrate,and good to excellent yields can be obtained.Notably,this reaction has been applied to the gram-scale synthesis of bioactive molecules.
基金the National Natural Science Foundation of China(No.22001034)Jiangxi Provincial Natural Science Foundation(No.20212BAB213001).
文摘A H_(4)SiW_(12)O_(40)-catalyzed three-component tandem reaction of 2-acylbenzoic acids,primary amines and phosphine oxides to form 3,3-disubstituted isoindolinones was developed.By employing A H_(4)SiW_(12)O_(40)as the catalyst and dimethyl carbonate(DMC)as the solvent,a diverse range of 2-acylbenzoic acid derivatives and primary amines worked well to give the C3-phosphinoyl-functionalized 3,3-disubstituted isoindolinones with the yield range of 61%-87%.Advantages of this transformation include green catalyst and solvent,available starting materials,broad substrate scope,high efficiency and operational simplicity with water as the sole by-product.The strategy achieved an efficient and green molecular fragment assembly to access isoindolinones,which would provide opportunities for the synthesis of potential biologically active molecules in a green manner.
基金the financial support from Nanjing University of Science and Technology.
文摘Cerium trichloride heptahydrate(CeCl_3·7H_2O) was found to be an efficient and recyclable catalyst for the three-component direct Mannich reaction of anilines and benzaldehydes with acetophenone.This protocol has advantages of high yield,no environmental pollution,mild condition,and simple work-up procedure.
