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Asymmetric photocatalysis over robust covalent organic frameworks with tetrahydroquinoline linkage 被引量:3
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作者 Chunzhi Li Yinhua Ma +5 位作者 Haoran Liu Lin Tao Yiqi Ren Xuelian Chen He Li Qihua Yang 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2020年第8期1288-1297,共10页
The asymmetric photocatalytic organic synthesis(APOS)process is a sustainable and environmentally benign method for the production of optically active chemicals with sunlight as an energy source.However,it still lacks... The asymmetric photocatalytic organic synthesis(APOS)process is a sustainable and environmentally benign method for the production of optically active chemicals with sunlight as an energy source.However,it still lacks efficient semiconductors with tunable band structures and has a low recycling stability.Herein,we report the synthesis of tetrahydroquinoline-linked covalent organic frameworks(QH-COFs)with irreversible tetrahydroquinoline linkage as efficient semiconductors for the visible-light-driven asymmetricα-alkylation of aldehydes by merging with a chiral secondary amine.Up to 94%ee was obtained over QH-COFs,and the activity of QH-COFs was significantly higher than those of inorganic semiconductors(e.g.,Ti O2,Bi VO4,and WO3)under similar conditions,which is mainly attributed to their narrow band gap and suitable band edge.As far as we know,QH-COFs are the most active semiconductors for asymmetricα-alkylation of aldehydes ever reported.The QH-COFs were prepared via a one-pot Povarov cascade imine formation and cycloaddition reaction using Sc(OTf)3/Yb(OTf)3 as Lewis acid catalysts.Attributed to the tetrahydroquinoline linkage,QH-COFs showed extremely high recycling stability,which made practicals application possible.This work not only opens up a new avenue for asymmetric photocatalysis but also provides an efficient and general method for the construction of robust COFs. 展开更多
关键词 PHOTOCATALYSIS Covalent organic frameworks tetrahydroquinoline linkage Asymmetric catalysis Ultrastability
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Imino Diels-Alder reactions:One-pot synthesis of tetrahydroquinolines 被引量:2
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作者 Vinod T.Kamble Bhaskar S.Davane +2 位作者 Sanjay A.Chavan Dnyanoba B.Muley Sandeep T.Atkore 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第3期265-268,共4页
An efficient synthesis of tetrahydroquinoline derivatives is reported via three component coupling reactions of aldehydes and anilines with various dienophiles in the presence of a catalytic amount of perchloric acid ... An efficient synthesis of tetrahydroquinoline derivatives is reported via three component coupling reactions of aldehydes and anilines with various dienophiles in the presence of a catalytic amount of perchloric acid adsorbed on silica gel(HClO;-SiO;) under mild reaction conditions. 展开更多
关键词 tetrahydroquinolineS HClO_4-SiO_2 DIENOPHILES ALDEHYDES AMINES
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Zirconyl Chloride Promoted Highly Efficient Domino Synthesis of New 1, 2, 3, 4-Tetrahydroquinoline Derivatives in Water 被引量:1
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作者 Rahul R.NAGAWADE Devanand B.SHINDE 《Chinese Chemical Letters》 SCIE CAS CSCD 2006年第9期1137-1140,共4页
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
关键词 ANILINES cyclic enol ether domino reaction tetrahydroquinoline zirconyl chloride
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Three-component one-pot synthesis of 1,2,3,4-tetrahydroquinoline derivatives in hexafluoroisopropanol 被引量:1
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作者 Jie Zhou Bai Ling Xu 《Chinese Chemical Letters》 SCIE CAS CSCD 2008年第8期921-924,共4页
The one-pot aza-Diels-Alder reaction of substituted aromatic amines, ethyl glyoxylate and benzyl vinylcarbamate or N- benzyloxycarbonyl 2-pyrroline was conducted in hexafluoroisopropanol, providing the desired 1,2,3,4... The one-pot aza-Diels-Alder reaction of substituted aromatic amines, ethyl glyoxylate and benzyl vinylcarbamate or N- benzyloxycarbonyl 2-pyrroline was conducted in hexafluoroisopropanol, providing the desired 1,2,3,4-tetrahydroquinline derivatives in moderate yields. 展开更多
关键词 Aza-Diels-Alder reaction tetrahydroquinoline Hexafluoroisopropanol (HFIP) Fluorinated solvent
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Remote stereocontrol in the(4+2)cycloadditions of 1,7-zwitterions:Asymmetric synthesis of multifunctionalized tetrahydroquinoline derivatives
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作者 Chen Chen Jin Zhou +5 位作者 Jing Jiang Yang Li Ting Mao Cheng Peng Gu Zhan Wei Huang 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第1期222-226,共5页
The scope of stereochemistry recognition usually occurs near the chiral scaffold of a ligand or catalyst.Remote stereocontrol,which can surpass the limits of stereorecognition of remote prochiral centers,has long been... The scope of stereochemistry recognition usually occurs near the chiral scaffold of a ligand or catalyst.Remote stereocontrol,which can surpass the limits of stereorecognition of remote prochiral centers,has long been a challenging object of great interest in asymmetric catalysis.The current work realized the remote stereocontrol of 1,7-zwitterion intermediates formed from Huang's o-amino aryl MBH carbonates.With simple and easily accessibleβ-ICD as the bifunctional catalyst,multifunctionalized tetrahydroquinoline derivatives could be synthesized via(4+2)cycloadditions with excellent enantioselectivity and diastereoselectivity under mild conditions.The strategy possesses broad substrate scope,and three types of electron-deficient enones are successfully applied.Mechanistic studies disclosed the Lewis base-catalyzed reaction pathway,and H-bonding between the catalyst and enones is crucial for long-range stereocontrol.Scale-up reaction and transformations of the tetrahydroquinoline products demonstrated the potential of this strategy. 展开更多
关键词 Asymmetric synthesis tetrahydroquinoline Remote stereocontrol PYRAZOLONE Lewis base catalysis 1 7-Zwitterion
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Rapid assembly of 1,3-indanedione-based spirocyclic tetrahydroquinolines for inducing human lung cancer cell apoptosis 被引量:1
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作者 Fen Tan Luojia Chen +6 位作者 Yuncong Yuan Xiaoyu He Yiwen Su Shuqiang Cao Conghua Xie Meijia Gu Youquan Zou 《Green Synthesis and Catalysis》 2022年第4期357-372,共16页
The rapid collection of a library of biologically relevant molecules is essential in new drug discovery.Here we show a variety of bioactive 1,3-indanedione-based spirocyclic tetrahydroquinolines that have been concise... The rapid collection of a library of biologically relevant molecules is essential in new drug discovery.Here we show a variety of bioactive 1,3-indanedione-based spirocyclic tetrahydroquinolines that have been concisely and efficiently constructed under the guidance of biology-oriented synthesis(BIOS).Using Pd(PPh_(3))_(4) as a catalyst,various 2-arylidene-1,3-indanediones can react with vinyl benzoxazinanones under the mild condition to afford a new class of spirocyclic tetrahydroquinolines in moderate to excellent yields(45%-99%)with high stereocontrol(>95:5 diastereoselectivity).Their structures were unambiguously confirmed by X-ray single crystal analysis.The biological evaluation revealed that two of the 1,3-indanedione-based spirocyclic tetrahydroquinolines show remarkable apoptosis-inducing activities over A549 human lung cancer cells,exceeding that of cisplatin.The antitur activities were triggered by reactive oxygen species,commonly overproduced in cancer cells.The clinical demand for antitumor chemotherapy for lung cancer has encouraged an all-out search for analogues with lower toxcity,improved therapeutic index and increased activity. 展开更多
关键词 Spirocyclic tetrahydroquinoline 1 3-Indanedione Lung cancer Apoptosis MITOCHONDRIA
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Imino Diels-Alder Reaction Catalyzed by Iodine: Efficient Synthesis of Tetrahydroquinolines
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作者 李云成 张俊民 +1 位作者 董立亭 鄢明 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2006年第7期929-932,共4页
Iodine was found to be an efficient catalyst for the imino Diels-Alder reaction of N-arylimine with enol ethers to provide tetrahydroquinolines in good yields. The influence of the loading of iodine, reaction solvent,... Iodine was found to be an efficient catalyst for the imino Diels-Alder reaction of N-arylimine with enol ethers to provide tetrahydroquinolines in good yields. The influence of the loading of iodine, reaction solvent, the structure of imine and enol ethers was studied. One pot synthesis of tetrahydroquinolines from aldehyde, aniline and enol ethers catalyzed by iodine was also applicable and provided tetrahydroquinolines in comparable yields. Mild reaction conditions, facile experimental procedure, low price of iodine and good yield of products render this new method attractive for practical synthesis of many tetrahydroquinoline derivatives. 展开更多
关键词 IODINE catalyst IMINE Diels-Alder reaction tetrahydroquinoline synthesis
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Porphyrin covalent organic framework for photocatalytic synthesis of tetrahydroquinolines
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作者 Chengjuan Wu Xinyu Li +4 位作者 Mingzhen Shao Jinglan Kan Guangbo Wang Yan Geng Yu-Bin Dong 《Chinese Chemical Letters》 SCIE CAS CSCD 2022年第10期4559-4562,共4页
A metal-free porphyrin covalent organic framework was employed as the heterogeneous photocatalyst for the synthesis of tetrahydroquinolines under aerobic conditions.With visible light irradiation of a catalytic amount... A metal-free porphyrin covalent organic framework was employed as the heterogeneous photocatalyst for the synthesis of tetrahydroquinolines under aerobic conditions.With visible light irradiation of a catalytic amount of H_(2)P-Bph-COF at room temperature,various substituted N,N-dimethylanilines and N-aryl maleimides were transformed to tetrahydroquinoline derivatives in moderate to good yields.This was the first example of the synthesis of tetrahydroquinolines via the photocatalytic aerobic annulation reaction employing the metal-free COF as the heterogeneous photocatalyst. 展开更多
关键词 tetrahydroquinolineS Photocatalytic oxidative annulation Covalent organic framework Heterogeneous photocatalyst PORPHYRIN
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One-Pot Stereoselective Synthesis of Different Fused Multicyclic Iminosugars Based on the Iminium-lon Intermediate
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作者 Song Xie Jilai Wu +3 位作者 Likai Zhou Chao Wei Xiaoliu Li Hua Chen 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第2期142-150,共9页
Different novel fused multicyclic iminosugars were synthesized from D-ribose tosylate,aniline and vinyl ethyl ether by one-pot three-component stereoselective[4+2]reaction at different temperatures.The iminium-ion is ... Different novel fused multicyclic iminosugars were synthesized from D-ribose tosylate,aniline and vinyl ethyl ether by one-pot three-component stereoselective[4+2]reaction at different temperatures.The iminium-ion is the key intermediate for the reaction.As a result,several complex fused iminosugars 3a were obtained by aza-Diels-Alder mechanism at 60℃,while a series of aza-C-glycosides 5a were prepared by Mannich reaction at room temperature accompanied by another tetrahydroquinoline-fused iminosugars 4a(tricyclic derivatives)through aza-Diels-Alder cycloaddition.This strategy will help to construct structurally diverse and bioactive iminosugar analogues. 展开更多
关键词 Fused multicyclic iminosugar Aza-Diels-Alder cycloaddition Mannich reaction tetrahydroquinoline Multicomponent reactions Enantioselectivity Cyclization
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Synthesis of tetrahydrofuro[3,2-b]quinolin-2(3H)-one derivatives from 2-aminobenzaldehydes and α-angelica lactone via a tandem Aldol/Michael addition
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作者 季泠 尹大伟 +1 位作者 王欣 李润涛 《Journal of Chinese Pharmaceutical Sciences》 CAS CSCD 2017年第3期163-172,共10页
An efficient synthesis of tetrahydrofuro[3,2-b]quinolin-2(3H)-ones from α-angelica lactone and 2-aminobenzaldehydes via a tandem Aldol-Michael addition is described. The reactions were carried out using DBU as the ... An efficient synthesis of tetrahydrofuro[3,2-b]quinolin-2(3H)-ones from α-angelica lactone and 2-aminobenzaldehydes via a tandem Aldol-Michael addition is described. The reactions were carried out using DBU as the base in i-Pr OH at 0 ℃, affording tetrahydrofuro[3,2-b]quinolin-2(3H)-ones in moderate to good yields. 展开更多
关键词 Aldol/Michael tandem cyclization tetrahydroquinoline FURANONE
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Kinetic Resolution of 2-Substituted 1,2-Dihydroquinolines by Rhodium-Catalyzed Asymmetric Hydroarylation 被引量:2
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作者 Baohua Cai Qingjing Yang +1 位作者 Ling Meng Jun(Joelle)Wang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2021年第6期1606-1610,共5页
A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via Rh-catalyzed asymmetric hydroarylation has been described for the first time.A variety of arylboronic acids coupled with 2-subst... A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via Rh-catalyzed asymmetric hydroarylation has been described for the first time.A variety of arylboronic acids coupled with 2-substituted 1,2-dihydroquinolines under mild reaction condition.The transformations into the enantio-enriched 2,3-diaryl-tetrahydroquinolines as well as the recovered chiral 2-aryl-dihydroquinolines were obtained with high yields and excellent enantioselectivities(86%-99% ee,s factor up to 1057). 展开更多
关键词 Kinetic resolution HYDROARYLATION tetrahydroquinoline Asymmetric catalysis Transition metal
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One Pot Synthesis of Medicinally Important cis-2.Methyl-4-am i no s u bstituted-1,2,3,4-tetrahyd roq u i nolines
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作者 Kiran,Kumar H.C Mahadevan,K.M +1 位作者 Prabhakara,VarmaP Srinivasa,A 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2012年第3期534-540,共7页
A simple synthesis of medicinally important cis-2-methyl-4-azapan-2-one-1,2,3,4-tetrahydroquinolines/cis-9- (2-methyl-l,2,3,4-tetrahydroquinolin-4-yl)-9H-carbazole was reported. Multicomponent one pot synthesis with... A simple synthesis of medicinally important cis-2-methyl-4-azapan-2-one-1,2,3,4-tetrahydroquinolines/cis-9- (2-methyl-l,2,3,4-tetrahydroquinolin-4-yl)-9H-carbazole was reported. Multicomponent one pot synthesis with ani- lines and N-vinylcaprolactam/N-vinyl carbazole via imino Diels-Alder reaction by using antimony trichloride as catalyst and acetonitrile as solvent was employed. NMR technique (2D) was used to study the regio- and stereo- chemistry of newly synthesized compounds. The cis diastereo-selectivity of the products was predicted by COSY and NOESY studies. 展开更多
关键词 imino Diels-Alder antimony trichloride tetrahydroquinoline N-VINYLCAPROLACTAM N-VINYLCARBAZOLE
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