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Molecular Docking Studies on Anticonvulsant Enaminones Inhibiting Voltage-Gated Sodium Channels
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作者 Yayin Fang Jamiya Kirkland +2 位作者 Isis J. Amaye Patrice Jackson-Ayotunde Matthew George Jr. 《Open Journal of Physical Chemistry》 2019年第4期241-257,共17页
Epilepsy is described as the most common chronic brain disorder. A typical symptom of epilepsy results in uncontrolled convulsions caused by temporary excessive neuronal discharges. Although several new anticon-vulsan... Epilepsy is described as the most common chronic brain disorder. A typical symptom of epilepsy results in uncontrolled convulsions caused by temporary excessive neuronal discharges. Although several new anticon-vulsants have been introduced, some types of seizures have still not been adequately controlled with these new and current therapies. There is an urgent need to develop new anticonvulsant drugs to control the many different types of seizures. Many studies have shown that the epilepsies involve more than one mechanism and therefore may be responsible for the various types of observed seizures. Recently reported studies have shown that a group of newly synthesized 6 Hz active anticonvulsant fluorinated N-benzamide enaminones exhibited selective inhibitions of voltage-gated sodium (Nav) channels. Nav channels are responsible for the initial inward currents during the depolarization phases of the action potential in excitable cells. The activation and opening of Nav channels result in the initial phases of action potentials. We hypothesize that there is an essential pharmacophore model for the interactions between these enaminones and the active sites of Nav channels. The research reported here is focused on molecular docking studies of the interactions that occur between the fluorinated N-benzamide enaminones and the Nav channels. These studies may open an avenue for designing anticonvulsant drugs by inhibiting Nav channels. 展开更多
关键词 ANTICONVULSANT enaminones VOLTAGE-GATED Sodium Channels STRUCTURE-BASED Drug Design MOLECULAR DOCKING 3D QSAR
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Facile Syntheses of New Pyrazolo[1,5-a]pyrimidines Derivatives via Reactions of Enaminones with Aminopyrazole
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作者 LI Ming WANG Shu-wen +1 位作者 WEN Li-rong KE Zi-qin 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 2005年第6期663-667,共5页
Ethyl 7-aryl-2-benzyhhiopyrazolo [ 1,5-a ] pyrimidine-3-carboxylates (3a-3f) were conveniently synthesized through the reactions of enaminones with 5-amino-3-benzyhhio4-ethoxycarbonyl-1 H-pyrazole in good yields and... Ethyl 7-aryl-2-benzyhhiopyrazolo [ 1,5-a ] pyrimidine-3-carboxylates (3a-3f) were conveniently synthesized through the reactions of enaminones with 5-amino-3-benzyhhio4-ethoxycarbonyl-1 H-pyrazole in good yields and high regioselectivity. The structures of the new compounds were fully characterized by spectroscopic measurmehts, elemental analysis and X-ray diffraction analysis. A plausible reaction mechanism for the formation of the title compounds was also presented. 展开更多
关键词 Pyrazolo [ 1 5-a ] pyrimidine ENAMINONE Synthesis Mechanism Crystal structure
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Synthesis of Novel Bis-enaminones by KHSO4-assisted Facile Michael Addition-elimination Reaction of 3-(dimethylamino)-1-phenylprop-2-en-1-ones with Diamines in Water
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作者 Asem Satyapati Devi Philippe Helissey Jai Narain Vishwakarma 《Green and Sustainable Chemistry》 2011年第2期31-34,共4页
3-(Dimethylamino)-1-phenylprop-2-en-1-ones (formylated acetophenones) 1 reacted with aliphatic diamines in water assisted by KHSO4 to give bis-enaminones 2a-h in good yields. Compound 1 also reacted with o-phenylenedi... 3-(Dimethylamino)-1-phenylprop-2-en-1-ones (formylated acetophenones) 1 reacted with aliphatic diamines in water assisted by KHSO4 to give bis-enaminones 2a-h in good yields. Compound 1 also reacted with o-phenylenediamine under similar conditions to produce bis-enaminones 3 instead of benzodiazepines 4 in excellent yields. 展开更多
关键词 ENAMINONE Bis-enaminone Formylated Acetophenone Michael ADDITION-ELIMINATION FORMYLATION Dimethylformamide-dimethylacetal
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Recent advances in visible light-mediated chemical transformations of enaminones 被引量:1
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作者 Yu Han Liyun Zhou +3 位作者 Chengyu Wang Shangti Feng Rong Ma Jie-Ping Wan 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第2期4-15,共12页
Enaminones,which possesses both the nucleophilic enamine as well as electrophilic enone structures,are well known versatile building blocks in organic synthesis.Meanwhile,visible light-mediated reactions have emerged ... Enaminones,which possesses both the nucleophilic enamine as well as electrophilic enone structures,are well known versatile building blocks in organic synthesis.Meanwhile,visible light-mediated reactions have emerged as useful synthetic strategy with enhanced sustainability.Around the last decade,various photochemical transformations of enaminones have been developed to construct cyclic or acyclic compounds.In this review,we describe the recent advances in visible light-mediated chemical transformations of enaminones.Detailed discussion on the reaction mechanism of the related reactions is given to provide guide to the reader.Finally,a summary on the existing challenges and the future outlook towards the development of practical photocatalytic reactions of enaminones is also presented. 展开更多
关键词 ENAMINONE Visible light C-H functionalization C=C bond cleavage CYCLIZATION Multicomponent reactions
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Chemodivergent Synthesis of Benzofurans and 2,3-Dihydrobenzofurans via Tandem Oxidative Annulation of Enaminones and Salicylaldehydes
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作者 Xiyan Duan Hui Li +5 位作者 Junqi Wang Kun Liu Meixin Shi Weidong Lian Ran Chen Pu Liu 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第15期1727-1733,共7页
Chemodivergent synthesis of benzofurans and 2,3-dihydrobenzofurans has been realized.Under a reaction system consisting of DBDMH and K_(2)CO_(3) as promotors,controlled conditions enabled the formation of two sets of ... Chemodivergent synthesis of benzofurans and 2,3-dihydrobenzofurans has been realized.Under a reaction system consisting of DBDMH and K_(2)CO_(3) as promotors,controlled conditions enabled the formation of two sets of valuable heterocycles from the tandem transformation of enaminones and salicylaldehydes.The key to success was the identification of the reaction parameters,in which the imine intermediate which was formed by transient halogenation coupling and substitution processes underwent either aldol condensation/annulation or imine hydrolysis/aldol condensation.The additives NH_(4)Cl or Fe_(2)(SO_(4))_(3) controlled the unique selectivity of this reaction.A broad substrate scope of enaminones and salicylaldehydes has been employed in this reaction,demonstrating excellent functional group tolerance and versatility. 展开更多
关键词 Cross-coupling UMPOLUNG Domino reactions ENAMINONE BENZOFURANS 2 3-Dihydrobenzofurans
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Highly selective synthesis of functionalized morphan derivatives through a multi-component cascade reaction of 3-formylchromones, 2-naphthols, and enaminones
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作者 Xinling Cao Yinggang Duan +3 位作者 Kaihong Lv Zihan Lu Yihua Chen Shengjiao Yan 《Green Synthesis and Catalysis》 2023年第4期321-329,共9页
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 liq... 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 reaction.This 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. 展开更多
关键词 Morphan derivatives Site-selective synthesis Cascade reaction enaminones 3-Formylchromones
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A solvent-free synthesis of 1,2,3,5-tetrasubstituted pyrroles from enaminones and α-haloketones
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作者 Issa Yavari Maryam Ghazvini +1 位作者 Leila Azad Tayebeh Sanaeishoar 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第10期1219-1222,共4页
A simple synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from the reaction of enaminone withα-haloketones,under solvent-free conditions,is described.
关键词 1H-Pyrrole ENAMINONE ar-Haloketone 1 3-Dicarbonyl compound SOLVENT-FREE
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Base-Promoted Synthesis of 3-Alkenyl-2-pyridones from N-Propargyl-β-enaminones and Aryl Aldehydes
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作者 Qingyu Tian Shangyun Xiao Guolin Cheng 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2021年第10期2781-2788,共8页
Main observation and conclusion In this article,we report a base-promoted sequential cyclization/aldol-type condensation/isomerization cascade reaction of N-propargyl-β-enaminones with aryl aldehydes.The key step in ... Main observation and conclusion In this article,we report a base-promoted sequential cyclization/aldol-type condensation/isomerization cascade reaction of N-propargyl-β-enaminones with aryl aldehydes.The key step in this protocol is the generation of 1,4-oxazepine anions from N-propargyl-β-enaminones under basic conditions,which are captured by aryl aldehydes.The method allows the formation of one pyridone core and one C—C double bond in“one pot”,and the preparation of a variety of densely decorated pyridone derivatives in moderate to good yields with broad functional group tolerance. 展开更多
关键词 Domino reactions Aldehydes ALKENES ENAMINONE PYRIDONES
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Metal-free C(sp^(2))-H perfluoroalkylsulfonylation and configuration inversion:Stereoselective synthesis ofα-perfluoroalkylsulfonyl E-enaminones
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作者 Qing Yu Yunyun Liu Jie-Ping Wan 《Chinese Chemical Letters》 SCIE CAS CSCD 2021年第11期3514-3517,共4页
The perfluoroalkylsulfonylation(CF_(3)SO_(2),C_(2)F_(5)SO_(2)and CHF_(2)SO_(2))in the enaminone C-H bonds has been developed simply via the promotion of molecular iodine by using stable and cheap sodium perfluoroalkyl... The perfluoroalkylsulfonylation(CF_(3)SO_(2),C_(2)F_(5)SO_(2)and CHF_(2)SO_(2))in the enaminone C-H bonds has been developed simply via the promotion of molecular iodine by using stable and cheap sodium perfluoroalkyl sulfinates as coupling partners.The stereoselective synthesis of E-configuratedα-perfluoroalkylsulfonyl enaminones has been realized via unprecedented C-H bond elaboration and C=C double bond configuration inversion by free radical process. 展开更多
关键词 C-H Functionalization ENAMINONE Perfluoroalkyl sulfonylation METAL-FREE Configuration inversion
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Reaction of Enaminones with Aminopyrazoles: Synthesis,Structures and Bioactivities of 7-Aryl-3-cyano-2-substituted Pyrazolo[1,5-a]pyrimidines
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作者 文丽荣 王书文 +1 位作者 李明 杨华铮 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2005年第9期1231-1235,共5页
The condensation reactions of 5-amino-4-cyano-3-substituted-1H-pyrazole 2 or 3 with enaminones 1 in the presence of glacial acetic acid gave twelve new 7-aryl-3-cyano-2-substituted pyrazolo[1,5-a]pyrimidines 4 and 5 a... The condensation reactions of 5-amino-4-cyano-3-substituted-1H-pyrazole 2 or 3 with enaminones 1 in the presence of glacial acetic acid gave twelve new 7-aryl-3-cyano-2-substituted pyrazolo[1,5-a]pyrimidines 4 and 5 at room temperature. Their structures were characterized by elemental analysis, IR and 1H NMR. The structure of 4a was further confirmed by X-ray crystallography analysis. A plausible reaction mechanism for the formation of the title compounds was also proposed. The bioassay tests showed that compounds 4a, 4e, 4e, 4f, 5a and 5d possessed moderate herbicidal activity. 展开更多
关键词 pyrazolo[1 5-a]pyrimidine ENAMINONE SYNTHESIS mechanism single crystal
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Synthesis and Crystal Structure of 5-Cyclopropyl- 10-(4-fluorophenyl)-7,7-dimethyl-7,8-dihydro-5H- indeno[1,2-b]quinoline-9,11(6H,10H)-dione
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作者 陈艳 屠树江 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 北大核心 2007年第9期1039-1042,共4页
The title compound 5-cyclopropyl-10-(4-fluorophenyl)-7,7-dimethyl-7,8-dihydro- 5H-indeno[1,2-b]quinolne-9,11(6H,10H)-dione was obtained by the reaction of 4-fluorobenzal- dehyde, 2H-indene-1,3-dione and 3-(cyclop... The title compound 5-cyclopropyl-10-(4-fluorophenyl)-7,7-dimethyl-7,8-dihydro- 5H-indeno[1,2-b]quinolne-9,11(6H,10H)-dione was obtained by the reaction of 4-fluorobenzal- dehyde, 2H-indene-1,3-dione and 3-(cyclopropylamino)-5,5-dimethylcyclohex-2-enone in the presence of acetic acid under microwave irradiation. Its structure was confirmed by IR and 1H- NMR spectra. The crystal is of monoclinic, space group P21/c with a = 14.138(3), b = 8.952(2), c = 17.140(3)A, β = 102.253(3)°, C27H24FNO2, Mr = 413.47, Z = 4, V = 2119.9(8)A^3, Dc = 1.296 g/cm^3, μ(MoKα) = 0.087 mm^-1, F(000) = 872, the final R = 0.0425 and wR = 0.0905 for 2336 observed reflections (I 〉 2σ(I)). X-ray analysis revealed that the pyridine ring adopts a boat conformation and the six-membered ring fused with it assumes a twist boat conformation. 展开更多
关键词 ALDEHYDES 1 3-indanedione enaminones synthesis microwave irradiation crystal structure
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Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives
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作者 Hamdi M Hassaneen Huwaida M. E Hassaneen Yasmin Sh Mohammed 《Natural Science》 2011年第8期651-660,共10页
The reaction of 1-methylisoquinoline 1 with hy-drazonoyl halides 2 in ethanol in the presence of chitosan under microwave irradiation affords triazoloisoquinoline 4. Product 4 reacts with dimethylformamide-dimethylace... The reaction of 1-methylisoquinoline 1 with hy-drazonoyl halides 2 in ethanol in the presence of chitosan under microwave irradiation affords triazoloisoquinoline 4. Product 4 reacts with dimethylformamide-dimethylacetal to give ena- minones 7 which react with hydrazonoyl halides to give pyrazolyl triazoloisoquinoline 13. Also, 1-methylisoquinoline 1 reacts with arylisothio-cyanate to give thioanilide 15 which reacts with hydrazonoyl halides to give the corresponding thiadiazolyl isoquinoline derivatives 20, 24. 展开更多
关键词 [1 2 4]Triazolo[3 4-a]isoquinolines enaminones Hydrazonoyl HALIDES CYCLOADDITION Reactions Chitosan Thioanilides 3 4]Thiadiazolylisoquinoline Derivatives
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Visible-Light-Induced Domino Cyclization to Access Pyrido[2,3-d]pyrimidine-2,4-diones via a Radical-Polar Crossover Reaction
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作者 Wanqing Zuo Yu Cheng +4 位作者 Zhizhen Zhu Lingling Zuo Xiao Geng Zhifang Li Lei Wang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第19期2346-2350,共5页
Comprehensive Summary Catalytic and green strategies for the synthesis of privileged scaffolds are synthetically appealing.We now report a radical-polar crossover(RPC)-enabled three-component cyclization of bromodiflu... Comprehensive Summary Catalytic and green strategies for the synthesis of privileged scaffolds are synthetically appealing.We now report a radical-polar crossover(RPC)-enabled three-component cyclization of bromodifluoroalkyls with enaminones and 6-aminouraciles via a visible-light-induced domino cyclization.The reaction exhibited a broad substrate scope(>40 examples)including complex molecules,which highlighted the utility of this strategy for the construction of a library of bioactive analogs. 展开更多
关键词 Photocatalysis HETEROCYCLES RADICALS Bromodifluoroalkyls 6-Aminouraciles enaminones
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Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under Solvent-Free Conditions
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作者 Wanqing Zuo Zhizhen Zhu +4 位作者 Yu Cheng Lingling Zuo Xiao Geng Zhifang Li Lei Wang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第12期1394-1398,共5页
Comprehensive Summary The development of switchable solvent-free multicomponent reactions to build high-value-added products is an important demand for organic synthesis.Herein,we detailed the successful implementatio... Comprehensive Summary The development of switchable solvent-free multicomponent reactions to build high-value-added products is an important demand for organic synthesis.Herein,we detailed the successful implementation of a switchable strategy for the construction of diverse 4-fluoroalkyl-1,4-dihydropyrimidines and 4-fluoroalkyl-pyrimidines via a solvent/additive-free[3+2+1]annulation,starting from readily available enamines,trifluoroacetaldehyde hydrate or 1-ethoxy-2,2-difluoroethanol and amidines hydrochloride.This reaction conforms to the concept of green synthesis,and provides a new avenue to access valuable fluorinated heterocycles. 展开更多
关键词 Fluorine chemistry Multicomponent reactions Environmental chemistry HETEROCYCLES enaminones AMIDINES
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Catalytic C-H activation-initiated transdiannulation:An oxygen transfer route to ring-fluorinated tricyclic γ-lactones
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作者 Qiuyun Li Yannan Zhu +4 位作者 Yining Wang Gang Qi Wen-Juan Hao Kelu Yan Bo Jiang 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第9期145-149,共5页
Catalytic C–H activation-initiated annulation reactions have emerged as a versatile strategy for the efficient construction of diverse ring structural units and complex cyclic molecules in synthetic chemistry.Herein,... Catalytic C–H activation-initiated annulation reactions have emerged as a versatile strategy for the efficient construction of diverse ring structural units and complex cyclic molecules in synthetic chemistry.Herein,we describe a new Rh(Ⅲ)-catalyzed C–H activation-initiated transdiannulation reaction of N,Ndimethyl enaminones with gem-difluorocyclopropenes in the presence of H_(2)O,enabling a facile and oxygen transfer access to ring-fluorinated tricyclicγ-lactones with a 6-5 ring-junction tetrasubstituted stereocenter.This approach features bond-forming/annulation efficiency,good functional group tolerance and complete regioselectivity,which may include a complex process consisting of Rh(Ⅲ)-catalyzed C(sp2)–H activation,cyclic alkene insertion,defluorinated ring-opening of gem-difluorocyclopropane,intramolecular oxygen transfer,intramolecular cyclization and oxidative hydration. 展开更多
关键词 C-H bond activation enaminones Transannulation Oxygen transfer Regioselectivity
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A two-step approach to 2-polyfluoroalkyl quinolines from N-aryl polyfluoroalkyl imidoyl iodides
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作者 Yu, HB Zang, QS Huang, WY 《Chinese Journal of Chemistry》 SCIE CAS CSCD 1997年第3期278-282,共5页
2-Polyfluoroalkyl quinoline derivatives were synthesized from the enaminones which were obtained from the reaction of FT-aryl polyfluoroalkyl imidoyl iodides with methyl ketones.
关键词 polyfluoroalkyl QUINOLINE ENAMINONE imidoyl iodides
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Amine-catalyzed synthesis of N^(2)-sulfonyl 1,2,3-triazole in water and the tunable N^(2)-H 1,2,3-triazole synthesis in DMSO via metal-free enamine annulation
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作者 Yanhui Guo Yunyun Liu Jie-Ping Wan 《Chinese Chemical Letters》 SCIE CAS CSCD 2022年第2期855-858,共4页
The selective synthesis of N^(2)-sulfonyl and N^(2)-H 1,2,3-triazoles via organocatalytic annulation of enaminone/enaminoester with sulfonyl azide has been realized. The unconventional selectivity providing N^(2)-sulf... The selective synthesis of N^(2)-sulfonyl and N^(2)-H 1,2,3-triazoles via organocatalytic annulation of enaminone/enaminoester with sulfonyl azide has been realized. The unconventional selectivity providing N^(2)-sulfoyl 1,2,3-triazoles takes place in pure water, wherein the hydrogen bond effect between water and the intermediate resulting from enamine-azide corporation accounts for the novel reaction selectivity. On the other hand, the reactions conducted in DMSO specifically afford N^(2)-H 1,2,3-triazoles in the absence of such hydrogen bond effect. 展开更多
关键词 ENAMINONE ANNULATION N^(2)-sulfonyl 1 2 3-triazole Selectivity Green synthesis Sulfonyl azide
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