β-Amino nitroalkenes are important elements in the medicinal research and organic synthetic chemistry.Despite many documented methods,a facile and convenient synthesis remains desirable so far.Herein,a direct nitrati...β-Amino nitroalkenes are important elements in the medicinal research and organic synthetic chemistry.Despite many documented methods,a facile and convenient synthesis remains desirable so far.Herein,a direct nitration of tertiary enamide with tert-butyl nitrite(tBuONO)under metal-free conditions is disclosed.A wide array of cyclic and acyclic enamides was nitrated with commercially available nonmetallic reagents,which produced diverse valuableβ-acylamino nitroalkenes in excellent yields.Furthermore,this protocol is operationally simple and exhibits broad substrate scope and good functional group compatibility.展开更多
A series of new ligands L_1-L_7 were readily prepared in one step.Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a novel Cu（Ⅱ）-L complex has been developed.The remarkable advantages of this rea...A series of new ligands L_1-L_7 were readily prepared in one step.Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a novel Cu（Ⅱ）-L complex has been developed.The remarkable advantages of this reaction are mild reaction conditions,simple workup procedure,high yields of products and the use of ethanol as a green solvent.展开更多
Highly efficient Michael addition reactions of malonates to nitroalkenes catalyzed by novel chiral thioureas derived from optically pure BINOL and amino acids are reported.Various trans-nitroalkenes reacted with malon...Highly efficient Michael addition reactions of malonates to nitroalkenes catalyzed by novel chiral thioureas derived from optically pure BINOL and amino acids are reported.Various trans-nitroalkenes reacted with malonates affording the desired products in up to 95%yield with excellent enantioselectivities(up to 97%ee).展开更多
As an effective alternative to Lewis-acid activation,hydrogen-bond donating(HBD)organo-catalysis represents a powerful construction tool for important classes of carbon-carbon bonds,wherein metal-organic frameworks(MO...As an effective alternative to Lewis-acid activation,hydrogen-bond donating(HBD)organo-catalysis represents a powerful construction tool for important classes of carbon-carbon bonds,wherein metal-organic frameworks(MOFs)alleviate issues like self-quenching,solubility and reactivity.However,sizeselectivity is rather challenging in such catalysis,while the status quo is still unexplored when both H-bonding and open-metal sites(OMS)are present together in a single system.The pillar-bilayer Cd(Ⅱ)MOF with a rare(3,8)-connected 2-nodal network upholds uni-directional microporous channels integrated with free-NH groups from the urea-moiety of the N,N-donor linker,and aqua-molecule bound[Cd_(3)(COO)_(6)]cluster.The activated framework allows the highly efficient Friedel-Crafts alkylation of indole and β-nitrostyrene under relatively mild conditions with low catalyst loading and no leaching.The strategically designed MOF exhibits unaltered activity over multiple catalytic cycles,and corroborates its effectivity towards a wide range of substituted electrophiles and nucleophiles.Importantly,suitably sized pores generated by two-fold interpenetration restrict the entry of a sterically encumbered substrate and result in poor conversion,demonstrating the rarest pore-fitting-induced size-selectivity.Given that this pore-engineered MOF contains both coordination unsaturated Cd(Ⅱ)centres and unbound-NH groups as active interaction sites,explicit proof of the interaction of the MOF functionality with the-NO_(2) group of the reactant is elaborated for the first time in light of the change in emission intensity of the framework in the presence of an electrophile,a judicious choice of substrate,and an in-depth comparison of the catalytic activity of an isostructural framework without a urea-moiety.These control experiments unprecedentedly authenticate urea-moiety-mediated two-point hydrogen bonding in the proposed catalytic route,and simultaneously exclude any major role for OMS at the SBU.Apart from pore-induced sizeexclusive reactions,this MOF exemplifies site-specific Friedel-Crafts alkylation,and paves the way to tailor-made engineering of advanced functionalities in contemporary materials for unconventional HBD reactions at the interface of structure-property synergies.展开更多
A simple, atom economical and highly efficient green protocol has been developed for the synthesis of Michael adducts of nitroalkenes and 2-amino-2-chromene derivatives by Michael addition of active methylene compoun...A simple, atom economical and highly efficient green protocol has been developed for the synthesis of Michael adducts of nitroalkenes and 2-amino-2-chromene derivatives by Michael addition of active methylene compounds （such as malononitrile and ethyl cyanoacetate） to nitroalkenes under aqueous-mediated conditions. This green approach provided the desired products in high yields and the reaction scope proved to be quite broad.展开更多
Allylindium bromide prepared by metallic indium and allyl bromide was added to nitroalkenes to give conjugate addition compounds in moderate to good yields in an aqueous media.
Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a novel Zn（II）-thiourea complex has been developed. The remarkable advantages of this reaction are mild reaction conditions, simple workup procedur...Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a novel Zn（II）-thiourea complex has been developed. The remarkable advantages of this reaction are mild reaction conditions, simple workup procedure, high yield of products and the use of ethanol as acceptable solvent.展开更多
Ethylenediamine （H2NCH2CHeNH2） was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane （or nitroethane）. When 1%-2% （tool%） of ethylenediamine was used as the catalys...Ethylenediamine （H2NCH2CHeNH2） was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane （or nitroethane）. When 1%-2% （tool%） of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane （or nitroethane） by refluxing for 3-10 h efficiently afforded various arylnitroalkenes la-ly in 85%-97% yields.展开更多
Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles toβ-nitroenones orβ-nitroacrylates was established with chiral scandium catalysts.It enabled the construction o...Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles toβ-nitroenones orβ-nitroacrylates was established with chiral scandium catalysts.It enabled the construction of functionalized 3,3-disubstituted oxindoles,including terminal and internal vinyl groups in excellent yields and ee values.展开更多
A facile and efficient 1, 4-conjungate addition（Michael addition） reaction of active methylene compounds to aft-unsaturated compounds, catalyzed by guanidinium lactate ionic liquid（IL9）, has been developed. A rang...A facile and efficient 1, 4-conjungate addition（Michael addition） reaction of active methylene compounds to aft-unsaturated compounds, catalyzed by guanidinium lactate ionic liquid（IL9）, has been developed. A range of chalcones and nitroalkenes together with active methylene compounds have been converted smoothly to the corresponding products in high yields.展开更多
Intermolecular Stetter reaction of aromatic aldehydes with（E）-（2-nitrovinyl）cyclohexane catalyzed by thiazolium A has been developed.The reaction rate and efficiency are profoundly impacted by the presence of thio...Intermolecular Stetter reaction of aromatic aldehydes with（E）-（2-nitrovinyl）cyclohexane catalyzed by thiazolium A has been developed.The reaction rate and efficiency are profoundly impacted by the presence of thiourea B.The reaction affords moderate to good yields of the Stetter product.Some factors influencing yield were discussed.展开更多
Nutrition plays a vital role in human health,particularly through the type and quality of dietary fats.While excessive saturated fatty acid(SFA)intake is associated with negative cardiovascular outcomes,unsaturated fa...Nutrition plays a vital role in human health,particularly through the type and quality of dietary fats.While excessive saturated fatty acid(SFA)intake is associated with negative cardiovascular outcomes,unsaturated fats especially monounsaturated(MUFA)and polyunsaturated fatty acids(PUFA)offer protective benefits.Among the bioactive lipids derived from unsaturated fats are nitrated fatty acids(NO2-FAs),electrophilic signaling molecules formed naturally during inflammation or via dietary interactions between nitrite-rich vegetables and unsaturated lipids.NO2-FAs have been shown to exert anti-inflammatory,antioxidant,and antiplatelet effects,influencing metabolic pathways involved in cardiometabolic health.This review explores the formation,meta-bolism,and biological actions of NO2-FAs from dietary sources,emphasizing their role within dietary patterns like the Mediterranean diet.By bridging lipid biochemistry and nutritional science,we underscore the therapeutic potential of NO2-FAs as diet-derived agents for disease prevention and treatment in metabolic and cardiovascular disorders.展开更多
基金Project supported by the Shandong Provincial Natural Science Foundation(Nos.ZR2023MB135,ZR2024QB086)the Qingchuang Technology Support Program of University in Shandong Province(No.2023KJ244)。
文摘β-Amino nitroalkenes are important elements in the medicinal research and organic synthetic chemistry.Despite many documented methods,a facile and convenient synthesis remains desirable so far.Herein,a direct nitration of tertiary enamide with tert-butyl nitrite(tBuONO)under metal-free conditions is disclosed.A wide array of cyclic and acyclic enamides was nitrated with commercially available nonmetallic reagents,which produced diverse valuableβ-acylamino nitroalkenes in excellent yields.Furthermore,this protocol is operationally simple and exhibits broad substrate scope and good functional group compatibility.
基金the financial support from the National Natural Science Foundation of China(Nos.20962018, 20862015,20762009 and 20562011)
文摘A series of new ligands L_1-L_7 were readily prepared in one step.Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a novel Cu（Ⅱ）-L complex has been developed.The remarkable advantages of this reaction are mild reaction conditions,simple workup procedure,high yields of products and the use of ethanol as a green solvent.
基金support from Natural Science Foundation of China(No.20772097)Sichuan Provincial Science Foundation for Outstanding Youth(No.05ZQ026-008)Key Project of the Education Department of Sichuan Province(No.2006A081).
文摘Highly efficient Michael addition reactions of malonates to nitroalkenes catalyzed by novel chiral thioureas derived from optically pure BINOL and amino acids are reported.Various trans-nitroalkenes reacted with malonates affording the desired products in up to 95%yield with excellent enantioselectivities(up to 97%ee).
基金the DST-SERB(grant no.CRG/2021/002529)the CSIR(grant no.MLP-0028)+1 种基金support from AESD&CIF(CSMCRI).CSMCRI communication no.220/2021.
文摘As an effective alternative to Lewis-acid activation,hydrogen-bond donating(HBD)organo-catalysis represents a powerful construction tool for important classes of carbon-carbon bonds,wherein metal-organic frameworks(MOFs)alleviate issues like self-quenching,solubility and reactivity.However,sizeselectivity is rather challenging in such catalysis,while the status quo is still unexplored when both H-bonding and open-metal sites(OMS)are present together in a single system.The pillar-bilayer Cd(Ⅱ)MOF with a rare(3,8)-connected 2-nodal network upholds uni-directional microporous channels integrated with free-NH groups from the urea-moiety of the N,N-donor linker,and aqua-molecule bound[Cd_(3)(COO)_(6)]cluster.The activated framework allows the highly efficient Friedel-Crafts alkylation of indole and β-nitrostyrene under relatively mild conditions with low catalyst loading and no leaching.The strategically designed MOF exhibits unaltered activity over multiple catalytic cycles,and corroborates its effectivity towards a wide range of substituted electrophiles and nucleophiles.Importantly,suitably sized pores generated by two-fold interpenetration restrict the entry of a sterically encumbered substrate and result in poor conversion,demonstrating the rarest pore-fitting-induced size-selectivity.Given that this pore-engineered MOF contains both coordination unsaturated Cd(Ⅱ)centres and unbound-NH groups as active interaction sites,explicit proof of the interaction of the MOF functionality with the-NO_(2) group of the reactant is elaborated for the first time in light of the change in emission intensity of the framework in the presence of an electrophile,a judicious choice of substrate,and an in-depth comparison of the catalytic activity of an isostructural framework without a urea-moiety.These control experiments unprecedentedly authenticate urea-moiety-mediated two-point hydrogen bonding in the proposed catalytic route,and simultaneously exclude any major role for OMS at the SBU.Apart from pore-induced sizeexclusive reactions,this MOF exemplifies site-specific Friedel-Crafts alkylation,and paves the way to tailor-made engineering of advanced functionalities in contemporary materials for unconventional HBD reactions at the interface of structure-property synergies.
文摘A simple, atom economical and highly efficient green protocol has been developed for the synthesis of Michael adducts of nitroalkenes and 2-amino-2-chromene derivatives by Michael addition of active methylene compounds （such as malononitrile and ethyl cyanoacetate） to nitroalkenes under aqueous-mediated conditions. This green approach provided the desired products in high yields and the reaction scope proved to be quite broad.
文摘Allylindium bromide prepared by metallic indium and allyl bromide was added to nitroalkenes to give conjugate addition compounds in moderate to good yields in an aqueous media.
基金This work was supported by the National Natural Science Foundation of China （Nos. 20962018, 20862015, 20762009 and 20562011）.
文摘Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a novel Zn（II）-thiourea complex has been developed. The remarkable advantages of this reaction are mild reaction conditions, simple workup procedure, high yield of products and the use of ethanol as acceptable solvent.
基金the National Natural Science Foundation of China （No. 20972048） and Shanghai Educational Development Foundation （The Dawn Program： No. 03SG27） for the financial support of this work.
文摘Ethylenediamine （H2NCH2CHeNH2） was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane （or nitroethane）. When 1%-2% （tool%） of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane （or nitroethane） by refluxing for 3-10 h efficiently afforded various arylnitroalkenes la-ly in 85%-97% yields.
基金financial support from the National Natural Science Foundation of China(No.21890723)。
文摘Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles toβ-nitroenones orβ-nitroacrylates was established with chiral scandium catalysts.It enabled the construction of functionalized 3,3-disubstituted oxindoles,including terminal and internal vinyl groups in excellent yields and ee values.
基金Supported by the Jilin University Innovation Fund(No.419070200033).
文摘A facile and efficient 1, 4-conjungate addition（Michael addition） reaction of active methylene compounds to aft-unsaturated compounds, catalyzed by guanidinium lactate ionic liquid（IL9）, has been developed. A range of chalcones and nitroalkenes together with active methylene compounds have been converted smoothly to the corresponding products in high yields.
基金supported by the Prospective Research Funds of Jiangsu Provincial Department of Science and Technology (No. BY2015049-02)the Open-end Funds of Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology, (No. 2014HS005)the Funds of Technology Research of Lianyungang (No. CG1301)
文摘Intermolecular Stetter reaction of aromatic aldehydes with（E）-（2-nitrovinyl）cyclohexane catalyzed by thiazolium A has been developed.The reaction rate and efficiency are profoundly impacted by the presence of thiourea B.The reaction affords moderate to good yields of the Stetter product.Some factors influencing yield were discussed.
基金the support of ANID-FONDECYT POSDOCTORAL 3220099,ANID-FONDECYT REGULAR No 1220339,FOVI240019 and FOVI240035,ANID/FONDEQUIP N°EQM200049ANID/DOCTORATE No.21221883CSIC-Uruguay,INIA-Fpta-Uruguay,and Programa de Desarrollo de las Ciencias B´asicas(PEDECIBA,Uruguay).
文摘Nutrition plays a vital role in human health,particularly through the type and quality of dietary fats.While excessive saturated fatty acid(SFA)intake is associated with negative cardiovascular outcomes,unsaturated fats especially monounsaturated(MUFA)and polyunsaturated fatty acids(PUFA)offer protective benefits.Among the bioactive lipids derived from unsaturated fats are nitrated fatty acids(NO2-FAs),electrophilic signaling molecules formed naturally during inflammation or via dietary interactions between nitrite-rich vegetables and unsaturated lipids.NO2-FAs have been shown to exert anti-inflammatory,antioxidant,and antiplatelet effects,influencing metabolic pathways involved in cardiometabolic health.This review explores the formation,meta-bolism,and biological actions of NO2-FAs from dietary sources,emphasizing their role within dietary patterns like the Mediterranean diet.By bridging lipid biochemistry and nutritional science,we underscore the therapeutic potential of NO2-FAs as diet-derived agents for disease prevention and treatment in metabolic and cardiovascular disorders.
