An efficiently catalytic method toward the synthesis of indolin-2-ones featuring an allylic derived C3-quaternary stereocenter via an intramolecular Heck cyclization/Suzuki coupling of N-substituted-N-(2-bromophenyl)a...An efficiently catalytic method toward the synthesis of indolin-2-ones featuring an allylic derived C3-quaternary stereocenter via an intramolecular Heck cyclization/Suzuki coupling of N-substituted-N-(2-bromophenyl)acrylamides and organoboron reagents was successfully developed by using a 1,3-bis(2,6-diisopropylphenyl)acenaphthoimidazol-2-ylidene(AnIPr)-ligated oxazoline palladacycle.It enabled a very broad substrate scope tolerating different functional groups,electronic properties and steric bulkiness.Notably,it revealed a great potential to build diverse heterocycle-fused indoline alkaloids via the same intermediate 3-allyl-1,3-dimethylindolin-2-one.展开更多
An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated a-keto esters was achieved by using trans-perhydroindolic acid ld as a chiral organocatalyst with excellent asymmetric behavior. Under the...An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated a-keto esters was achieved by using trans-perhydroindolic acid ld as a chiral organocatalyst with excellent asymmetric behavior. Under the opti- mal reaction conditions, products with more than 99% de and up to 93% ee were obtained in high chemical yield （up to 98%） for a series of β,γ-unsaturated a-keto esters. The methodology provided an efficient route to dihydro- pyran derivatives containing many substituent groups （including amino groups）.展开更多
A domino reaction of anilines with cyclic and acyclic enol ethers induced by catalytic amounts of TBPA^（·＋）（5 mol%） was investigated and a series of 2,4-disubstituted-1,2,3,4-tetrahydroquinolines were synthe...A domino reaction of anilines with cyclic and acyclic enol ethers induced by catalytic amounts of TBPA^（·＋）（5 mol%） was investigated and a series of 2,4-disubstituted-1,2,3,4-tetrahydroquinolines were synthesized.Different from cyclic enol ethers, when acyclic enol ethers were used in the reaction,they serve as surrogates of acetaldehyde,producing a series of 2-methyl-4- anilino-1,2,3,4-tetrahydroquinolines.A single electron transfer mechanism was proposed to rationalize the products formation.展开更多
The functionalized arylidene bis（3-arylaminoacrylates） were efficiently prepared by FeCl3 catalyzed one-pot domino reactions of primary amines, methyl propiolate and aromatic aldehydes. When isatins were utilized un...The functionalized arylidene bis（3-arylaminoacrylates） were efficiently prepared by FeCl3 catalyzed one-pot domino reactions of primary amines, methyl propiolate and aromatic aldehydes. When isatins were utilized under similar conditions, only 2-oxoindolinyl 3-arylaminoacrylates were obtained in moderate yields. ^1H NMR data and single crystal structures indicated that this reaction has high diastereoselectivity.展开更多
Copper hydride-catalyzed conjugate reduction-intermolecular aldol addition domino reactions were realized using α,β-unsaturated carboxylates as hydride acceptors and a silane as the reducing reagent. High diastereos...Copper hydride-catalyzed conjugate reduction-intermolecular aldol addition domino reactions were realized using α,β-unsaturated carboxylates as hydride acceptors and a silane as the reducing reagent. High diastereoselec- tivities were achieved with 4,5-bis（diphenylphosphino）-9,9-dimethylxanthene as the ligand and tert-butyl acrylate as the hydride acceptor.展开更多
Imidazo[1,2-a]pyridines have been successfully synthesized in moderate to good yields via a tandem three- component reaction of ethyl 2-（3-oxo-3-arylpropanethioamido）acetates with aromatic aldehydes and malononitril...Imidazo[1,2-a]pyridines have been successfully synthesized in moderate to good yields via a tandem three- component reaction of ethyl 2-（3-oxo-3-arylpropanethioamido）acetates with aromatic aldehydes and malononitrile by means of microwave irradiation using DABCO as the catalyst. The advantages of this method including high chemo- and regioselectivity make this new strategy highly attractive.展开更多
A novel and concise method for the construction ofγ-nitro ketones and 1,3-dinitro compounds with chemo-selective acyl transfer has been presented under basic conditions via one-pot reactions.These reactions feature h...A novel and concise method for the construction ofγ-nitro ketones and 1,3-dinitro compounds with chemo-selective acyl transfer has been presented under basic conditions via one-pot reactions.These reactions feature high atom-and step-economic possess,mild condition and simple operation for one-pot synthesis of aliphatic nitro compounds.This protocol provides the products in good yields.The possible reaction mechanism has also been proposed.展开更多
We have developed an N-heterocyclic carbene(NHC)-catalyzed domino reaction with aryl alde-hyde through a simple acyl azolium intermediate using phenyliodine(III)diacetate(PIDA)as an oxi-dant.Controlled experiments and...We have developed an N-heterocyclic carbene(NHC)-catalyzed domino reaction with aryl alde-hyde through a simple acyl azolium intermediate using phenyliodine(III)diacetate(PIDA)as an oxi-dant.Controlled experiments and density functional theory calculations supported a domino two-stage mechanism from aldehyde/amine to anα-oxygen-ation product,including NHC-catalyzed oxidation of the aldehyde to carboxylic acid via acyl azolium intermediate,and further,an addition of carboxyl-ate to iminium intermediate.Our study reveals a new model for the oxidation of Breslow intermedi-ate via electrophilic attack of the hydroxyl group by PIDA.展开更多
NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists...NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5-trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method could also apply to other trifluoromethyl-substituted enones.展开更多
An efficient,convenient and environmentally benign procedure for the synthesis of novel 3-oxo-3Hbenzo[a]pyrano[2.3-c]phenazine-l-carboxylate and 3-（5-hydroxybenzo[a]phenazin-6-yl） acrylate derivatives has been devel...An efficient,convenient and environmentally benign procedure for the synthesis of novel 3-oxo-3Hbenzo[a]pyrano[2.3-c]phenazine-l-carboxylate and 3-（5-hydroxybenzo[a]phenazin-6-yl） acrylate derivatives has been developed by domino three-component condensation reaction between 2-hydroxynaphthalene-1,4-dione,benzene-1,2-diamines and acetylenic esters in the presence of a catalytic amount of DABCO as an expedient,eco-friendly and reusable base catalyst in water.This green process produces biologically and pharmacologically significant heterocycles in a one-pot single operation and offers considerable advantages such as：operational simplicity,short reaction time,high yields,reusability of catalyst,absence of any tedious workup or purification and avoids hazardous reagents/solvents.展开更多
The tetrahydroquinoline moiety is a structural feature of many natural products. By using a domino reaction of aromatic amines and cyclic enol ethers catalyzed by zirconyl chloride in water, various tetrahydroquinolin...The tetrahydroquinoline moiety is a structural feature of many natural products. By using a domino reaction of aromatic amines and cyclic enol ethers catalyzed by zirconyl chloride in water, various tetrahydroquinoline derivatives were synthesized efficiently. Most cyclized products showed cis selectivity. The cis selectivity was tentatively rationalized due to chelation control in water.展开更多
An efficient synthetic protocol for the 1,4-diaryl-1,4-dihydropyridines was developed via the domino four-component reaction of arylamine,acetylenedicarboxylate,aromatic aldehyde and ethyl acetoacetate.The reaction me...An efficient synthetic protocol for the 1,4-diaryl-1,4-dihydropyridines was developed via the domino four-component reaction of arylamine,acetylenedicarboxylate,aromatic aldehyde and ethyl acetoacetate.The reaction mechanism involves the formation of β-enamino ester and its sequential Michael addition to arylidene acetoacetate.展开更多
基金National Natural Science Foundation of China(No.22101133)Natural Science Foundation of Jiangsu Province(No.BK20200768)and Nanjing Forestry University are greatly acknowledged.
文摘An efficiently catalytic method toward the synthesis of indolin-2-ones featuring an allylic derived C3-quaternary stereocenter via an intramolecular Heck cyclization/Suzuki coupling of N-substituted-N-(2-bromophenyl)acrylamides and organoboron reagents was successfully developed by using a 1,3-bis(2,6-diisopropylphenyl)acenaphthoimidazol-2-ylidene(AnIPr)-ligated oxazoline palladacycle.It enabled a very broad substrate scope tolerating different functional groups,electronic properties and steric bulkiness.Notably,it revealed a great potential to build diverse heterocycle-fused indoline alkaloids via the same intermediate 3-allyl-1,3-dimethylindolin-2-one.
文摘An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated a-keto esters was achieved by using trans-perhydroindolic acid ld as a chiral organocatalyst with excellent asymmetric behavior. Under the opti- mal reaction conditions, products with more than 99% de and up to 93% ee were obtained in high chemical yield （up to 98%） for a series of β,γ-unsaturated a-keto esters. The methodology provided an efficient route to dihydro- pyran derivatives containing many substituent groups （including amino groups）.
基金We thank NSFC(No.21002079)Project(No.20096203120002)supported by the Ministry of Education of the People's Republic of China.We also thank the third Knowledge and Technological Innovation Project(No.NWNUKJCXGC -03-75 and NWNU-KJCXGC-03-64) of Northwest Normal University for supporting our research
文摘A domino reaction of anilines with cyclic and acyclic enol ethers induced by catalytic amounts of TBPA^（·＋）（5 mol%） was investigated and a series of 2,4-disubstituted-1,2,3,4-tetrahydroquinolines were synthesized.Different from cyclic enol ethers, when acyclic enol ethers were used in the reaction,they serve as surrogates of acetaldehyde,producing a series of 2-methyl-4- anilino-1,2,3,4-tetrahydroquinolines.A single electron transfer mechanism was proposed to rationalize the products formation.
基金This work was financially supported by the National Natural Science Foundation of China （Grant No. 21172189） and the Priority Academic Program Devel- opment of Jiangsu Higher Education Institutions.
文摘The functionalized arylidene bis（3-arylaminoacrylates） were efficiently prepared by FeCl3 catalyzed one-pot domino reactions of primary amines, methyl propiolate and aromatic aldehydes. When isatins were utilized under similar conditions, only 2-oxoindolinyl 3-arylaminoacrylates were obtained in moderate yields. ^1H NMR data and single crystal structures indicated that this reaction has high diastereoselectivity.
文摘Copper hydride-catalyzed conjugate reduction-intermolecular aldol addition domino reactions were realized using α,β-unsaturated carboxylates as hydride acceptors and a silane as the reducing reagent. High diastereoselec- tivities were achieved with 4,5-bis（diphenylphosphino）-9,9-dimethylxanthene as the ligand and tert-butyl acrylate as the hydride acceptor.
文摘Imidazo[1,2-a]pyridines have been successfully synthesized in moderate to good yields via a tandem three- component reaction of ethyl 2-（3-oxo-3-arylpropanethioamido）acetates with aromatic aldehydes and malononitrile by means of microwave irradiation using DABCO as the catalyst. The advantages of this method including high chemo- and regioselectivity make this new strategy highly attractive.
基金supported financially by the National Natural Science Foundation of China(21172227).
文摘A novel and concise method for the construction ofγ-nitro ketones and 1,3-dinitro compounds with chemo-selective acyl transfer has been presented under basic conditions via one-pot reactions.These reactions feature high atom-and step-economic possess,mild condition and simple operation for one-pot synthesis of aliphatic nitro compounds.This protocol provides the products in good yields.The possible reaction mechanism has also been proposed.
基金Financial support from the National Natural Science Foundation of China(Grant#s:21425207,21521002,21573233,and 21672216)the Chinese Academy of Sciences is greatly acknowledged.
文摘We have developed an N-heterocyclic carbene(NHC)-catalyzed domino reaction with aryl alde-hyde through a simple acyl azolium intermediate using phenyliodine(III)diacetate(PIDA)as an oxi-dant.Controlled experiments and density functional theory calculations supported a domino two-stage mechanism from aldehyde/amine to anα-oxygen-ation product,including NHC-catalyzed oxidation of the aldehyde to carboxylic acid via acyl azolium intermediate,and further,an addition of carboxyl-ate to iminium intermediate.Our study reveals a new model for the oxidation of Breslow intermedi-ate via electrophilic attack of the hydroxyl group by PIDA.
基金Supports from the National Natural Science Foundation of China (Nos. 21272257, 21274041 and 21474028)
文摘NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5-trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method could also apply to other trifluoromethyl-substituted enones.
基金financial support from the Research Council of Young ResearchersElite Club of the Islamic Azad University of YazdUniversity of Sistan and Baluchestan
文摘An efficient,convenient and environmentally benign procedure for the synthesis of novel 3-oxo-3Hbenzo[a]pyrano[2.3-c]phenazine-l-carboxylate and 3-（5-hydroxybenzo[a]phenazin-6-yl） acrylate derivatives has been developed by domino three-component condensation reaction between 2-hydroxynaphthalene-1,4-dione,benzene-1,2-diamines and acetylenic esters in the presence of a catalytic amount of DABCO as an expedient,eco-friendly and reusable base catalyst in water.This green process produces biologically and pharmacologically significant heterocycles in a one-pot single operation and offers considerable advantages such as：operational simplicity,short reaction time,high yields,reusability of catalyst,absence of any tedious workup or purification and avoids hazardous reagents/solvents.
文摘The tetrahydroquinoline moiety is a structural feature of many natural products. By using a domino reaction of aromatic amines and cyclic enol ethers catalyzed by zirconyl chloride in water, various tetrahydroquinoline derivatives were synthesized efficiently. Most cyclized products showed cis selectivity. The cis selectivity was tentatively rationalized due to chelation control in water.
基金Supported by the National Natural Science Foundation of China(No.20972132)the Fund of Key Laboratory of Environmental Resource and Material,Jiangsu Province,China
文摘An efficient synthetic protocol for the 1,4-diaryl-1,4-dihydropyridines was developed via the domino four-component reaction of arylamine,acetylenedicarboxylate,aromatic aldehyde and ethyl acetoacetate.The reaction mechanism involves the formation of β-enamino ester and its sequential Michael addition to arylidene acetoacetate.
