- Synthesis and characterisation of Hg (II) and Ag (I) complexes of 4-fluorobenzoylmethylenetriphenylphosphorane and 4-chlorobenzoyl methylenetriphenylphosphorane, with spectroscopic studies
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4-flourobenzyloxymethylenetriphenylphosphorane ylide [Ph 3PCHCOC6H4F], (FBPPY), and 4- chlorobenzyloxymethylenetriphenylphosphorane ylide [Ph3PCHCOC 6H4Cl](CBPPY), have been synthesised. Th
- Karami, Kazem
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- One-pot synthesis of new hydantoin (thiohydantoin) derivatives and evaluation of their antibacterial and antioxidant activities
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One-pot four-component reactions of phenacyl bromides, parabanic or thioparabanic acids, thiophenols, and triphenylphosphine in the presence of triethylamine afforded new derivatives of hydantoin or thiohydantoin in good to high yields (65%-90%). Their an
- Ghasempour, Leila,Asghari, Sakineh,Tajbakhsh, Mahmood,Mohseni, Mojtaba
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- Substituent effects in the formation of a few acenaphthenone-2-ylidene ketones and their molecular docking studies and in silico ADME profile
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We observed intriguing substituent effects in the reaction between 4-substituted acetophenones and acenaphthenequinone in the presence of KOH in methanol. In all cases, expected Claisen-Schimdt condensation was the first step. However, depending on the nature of 4-substituent on acetophenone, the initially formed condensation product remain unchanged or underwent Domino sequence of reactions to give three different 2:2 adducts arising through three distinct pathways. The interactions of acenaphthenone-2-ylidene ketones with the target proteins were performed by molecular docking studies. The prediction of in silico ADME belongings of the synthesized compounds revealed substantial drug-likeness characters based on Lipinski's rules.
- A, Jesna,Jacob, Jomon P.,Kuriakose, Daly,Thumpakara, Roshini K.
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- Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions
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The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.
- Fu, Haigen,Lam, Heather,Emmanuel, Megan A.,Kim, Ji Hye,Sandoval, Braddock A.,Hyster, Todd K.
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p. 9622 - 9629
(2021/07/01)
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- Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides
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Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).
- Liu, Xin,Werner, Thomas
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p. 1096 - 1104
(2020/12/31)
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- Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers
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The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.
- De Bruin, Bas,De Zwart, Felix J.,Li, Zirui,Mathew, Simon,Wolzak, Lukas A.,Zhou, Minghui
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supporting information
p. 20501 - 20512
(2021/12/03)
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- Rh(iii)-catalyzed diastereoselective cascade annulation of enone-tethered cyclohexadienonesviaC(sp2)-H bond activation
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Herein, we report highly diastereoselective arylative cyclization of enone-tethered cyclohexadienonesviaRh(iii)-catalyzed C-H activation ofN-methoxybenzamides. This reaction proceeds through the formation of a five-membered rhodacycle followed by bis-Michael cascade annulation to access functionalized bicyclic scaffolds with four contiguous stereocenters with a broad substrate scope. These products have excellent functional handles, allowing further synthetic transformation to increase the structural complexity. Furthermore, mechanistic studies of arylative cyclization and a gram-scale experiment are also presented.
- Chegondi, Rambabu,Jadhav, Sandip B.,Maurya, Sundaram,Navaneetha, N.
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p. 13598 - 13601
(2021/12/23)
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- Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines
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The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.
- Ding, Xiaojuan,Duan, Jindian,Fang, Zheng,Guo, Kai,Li, Zhenjiang,Mao, Yiyang,Rong, Binsen,Xu, Gaochen,Zhang, Lei,Zhu, Ning
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supporting information
p. 2532 - 2542
(2020/03/13)
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- C(sp2)-H Bond Multiple Functionalization in Air for Construction of Tetrahydrocarbazoles with Continuous Quaternary Carbons and Polycyclic Diversification
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The C(sp2)-H function of indole ketone with diazo compound via a rhodium(II)-catalyzed intramolecular electrophilic trapping reaction under mild conditions in air was demonstrated. The established methodology provided a highly efficient approach for direct synthesis of mutisubstituted tetrahydrocarbazoles with continuous quaternary carbons. The resulting products facilitate further modification to conveniently construct tetrahydrocarbazoles with additional fused heterocyclic rings. By phenotypic screening, several products exhibit good anticancer bioctivities in osteosarcoma cell lines.
- Dong, Suzhen,Jia, Shikun,Liu, Shunying,Ni, Dan,Pi, Rou,Song, Longlong,Tang, Jie,Yang, Fan
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- Visible-light driven synthesis of polycyclic benzo[: D] [1,3]oxazocine from 2-aminochalcone
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Herein, we report a tandem cycloisomerization/nucleophilic addition/cyclization of 2-amino chalcone with bifunctional nucleophiles driven by visible light. This cascade process is realized by the irradiation of a blue LED at room temperature, which provides a concise route to structurally diverse benzo[d][1,3]oxazocine scaffolds. Mechanistic studies show that the reaction is initiated with the E to Z isomerization of a C-C double bond upon the irradiation of visible light, followed by cyclization/rearomatization to generate a transient quinolinium intermediate, which is trapped by the nucleophile and cyclized to produce the polycyclic benzo[d][1,3]oxazocine.
- Chen, Junhan,Gao, Yu-Qi,He, Yu-Peng,Hou, Yi,Li, Ruoxin,Xie, Weiqing,Zhang, Sheng-Yong,Zhu, Liming
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supporting information
p. 6739 - 6742
(2020/07/13)
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- Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond to Form Two Stereogenic Centers in an Aqueous Medium
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Organocatalytic selenosulfonylation of the C-C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.
- Chen, Zhili,Hu, Fangli,Huang, Shengli,Zhao, Zhengxing,Mao, Hui,Qin, Wenling
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p. 8100 - 8111
(2019/06/17)
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- PYRROLIDINE DERIVATIVES AS PPAR AGONISTS
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The present invention discloses a class of pyrrolidine derivatives as PPAR agonist, and their use for the treatment of some diseases of PPAR receptor-associated pathways (such as nonalcoholic steatohepatitis and concurrent fibrosis, insulin resistance, primary biliary cholgangitis, dyslipidenmia, hyperlipidemia, hypercholesterolemia, atherosclerosis, hypertriglyceridemia, cardiovascular disease, obesity or the like). In particular, the present invention discloses a compound represented by Formula (I) or a pharmaceutically acceptable salt thereof.
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- Tandem Wittig Reaction-Ring Contraction of Cyclobutanes: A Route to Functionalized Cyclopropanecarbaldehydes
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An original tandem reaction consisting of a Wittig reaction-ring contraction process between α-hydroxycyclobutanone and phosphonium ylides has been developed. Highly functionalized cyclopropanecarbaldehydes are obtained in good to high yield.
- Aitken, David J.,Caboni, Pierluigi,Cuccu, Federico,Frongia, Angelo,Luridiana, Alberto,Secci, Francesco,Serusi, Lorenzo
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supporting information
(2019/10/08)
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- Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents
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Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.
- Farley, Conner M.,Zhou, You-Yun,Banka, Nishit,Uyeda, Christopher
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p. 12710 - 12714
(2018/10/09)
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- Nonenzymatic Dynamic Kinetic Resolution of in situ Generated Hemithioacetals: Access to 1,3-Disubstituted Phthalans
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The first nonenzymatic DKR reaction of hemithioacetals is developed. Hemithioacetals were formed in situ via thiol addition and subsequently underwent an intramolecular oxa-Michael reaction. The scope of the reaction was quite broad ranging from aliphatic to aromatic substituents and 1,3-disubstituted-1,3-dihyroisobenzofuran products were obtained in good yields with moderate diastereoselectivities and high enantioselectivities. (Figure presented.).
- Nath, Utpal,Chowdhury, Deepan,Pan, Subhas Chandra
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supporting information
p. 1628 - 1633
(2018/03/21)
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- Novel hybrids derived from aspirin and chalcones potently suppress colorectal cancer in vitro and in vivo
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Colorectal cancer (CRC) remains the fourth leading cause of cancer deaths around the world despite the availability of many approved small molecules for treatment. The issues lie in the potency, selectivity and targeting of these compounds. Therefore, new
- Lu, Shan,Obianom, Obinna N.,Ai, Yong
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p. 1722 - 1732
(2018/10/26)
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- Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction
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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.
- Liu, Xiao-Dong,Ma, Hai-Yan,Xing, Chun-Hui,Lu, Long
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p. 1780 - 1783
(2017/07/27)
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- A convenient synthesis of 4-alkyl-3-benzoylpyrroles from α,β-unsaturated ketones and tosylmethyl isocyanide
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A convenient synthesis of 4-alkyl-3-benzoyl pyrrole was achieved from α,β-unsaturated ketones and tosylmethyl isocyanide in the presence of mild base LiOH·H2O. This method is very economical and was successfully utilized for the synthesis of various 4-alkyl-3-benzoylpyrrole derivatives with good to excellent yields.
- Kumar, Kapil,More, Shital S.,Goyal, Sandeep,Gangar, Mukesh,Khatik, Gopal L.,Rawal, Ravindra K.,Nair, Vipin A.
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p. 2315 - 2319
(2016/05/10)
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- Iodine-mediated intramolecular amination of ketones: The synthesis of 2-acylindoles and 2-acylindolines by tuning N-protecting groups
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A general method for constructing both 2-acylindoles and 2-acylindolines via I2-mediated intramolecular C-N bond formation is presented, and the selective formation of either 2-acylindoles or 2-acylindolines just depends on the nitrogen protecting groups used in the same substrate skeletons. The Royal Society of Chemistry.
- Gao, Wen-Chao,Jiang, Shan,Wang, Ruo-Lin,Zhang, Chi
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p. 4890 - 4892
(2013/07/05)
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- Isothiourea-mediated one-pot synthesis of functionalized pyridines
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Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/ lactamization, thiophenol elimination, and N- to O
- Stark, Daniel G.,Morrill, Louis C.,Yeh, Pei-Pei,Slawin, Alexandra M. Z.,O'Riordan, Timothy J. C.,Smith, Andrew D.
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supporting information
p. 11642 - 11646
(2013/11/06)
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- Identification of novel chromenone derivatives as interleukin-5 inhibitors
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A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety.
- Venkateswararao, Eeda,Kim, Min-Seok,Sharma, Vinay K.,Lee, Ki-Cheul,Subramanian, Santhosh,Roh, Eunmiri,Kim, Youngsoo,Jung, Sang-Hun
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- Edge-shared [M2Cl10]2-Complexes of reaction between oxophilic group IV metal and phosphorus ylides
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The reactions between oxophilic group 4 metal chlorides, a-keto ylides in THF, led to the formation of titanium, zirconium and hafnium edge-shared [M 2Cl10]2- complexes (1a-3d). With adding dimethyl sulfoxide as a ligand t
- Sabounchei, Seyyed Javad,Ahmadi, Mohsen,Shahriary, Parisa
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scheme or table
p. 1333 - 1337
(2012/09/07)
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- Edge-Shared [M2Cl10]2- complexes of reaction between oxophilic group 4 metal and phosphorus ylides1
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The reactions between oxophilic group 4 metal chlorides, α-keto ylides in THF, led to the forma-tion of titanium, zirconium and hafnium edge-shared [M2Cl10]2- complexes (1a-3f). We describe that the reaction between MClsu
- Sabounchei,Ahmadi,Shahriari,Hoseini-Fashami,Samiee
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p. 1005 - 1013
(2012/10/08)
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- Organocatalytic Functionalization of carboxylic acids: Isothiourea- catalyzed asymmetric intra- and intermolecular Michael addition-lactonizations
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Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and α-keto-β,γ-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).
- Belmessieri, Dorine,Morrill, Louis C.,Simal, Carmen,Slawin, Alexandra M. Z.,Smith, Andrew D.
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supporting information; experimental part
p. 2714 - 2720
(2011/04/23)
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- Highly efficient route to functionalized tetrahydrocarbazoles using a tandem cross-metathesis/intramolecular-hydroarylation sequence
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The scope of the novel ruthenium-catalyzed tandem cross-metathesis/ intramolecular-hydroarylation sequence is described. This methodology offers a practical and efficient synthesis of structurally diverse and complex tetrahydrocarbazoles in good to excellent yields (up to 98%). Moreover, preliminary efforts towards the development of an enantioselective version of the current process by sequential catalysis with ruthenium complex and chiral amine are presented, with high yields and enantioselectivities (up to 88% yield and 91% ee).
- An, Xiao-Lei,Chen, Jia-Rong,Li, Chang-Feng,Zhang, Fu-Gen,Zou, You-Quan,Guo, Ying-Cen,Xiao, Wen-Jing
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p. 2258 - 2265
(2011/06/11)
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- Synthesis and characterization of new nitrate-bridged polymeric complexes of mercury(II) with phosphorus ylides
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Reaction of phosphorus ylides of the type X-C6H4-COCH{double bond, long}PAr3 (X = Cl and NO2; Ar = phenyl and p-tolyl) with Hg(NO3)2 · H2O in equimolar ratios using methanol as s
- Sabounchei, Seyyed Javad,Nemattalab, Hassan,Khavasi, Hamid Reza
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p. 5440 - 5446
(2008/03/12)
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- Synthesis, thermal reactivity and kinetics of substituted [(benzoyl)(phenylcarbamoyl)methylene]triphenylphosphoranes and their thiocarbamoyl analogues
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A range of 16 substituted benzoyl/arylcarbamoyl and benzoyl/ arylthiocarbamoyl stabilised ylides have been prepared. They are found under conditions of flash vacuum pyrolysis to fragment giving a benzoyl ylide and aryl isocyanate or isothiocyanate accompanied in some cases by secondary pyrolysis products. Kinetic studies show the thiocarbamoyl ylides to react consistently faster than their carbamoyl analogues and substituent effects suggest a polar cyclic transition state, which involves attack by the benzoyl oxygen on the carbamoyl/thiocarbamoyl NH. Graphical Abstract.
- Aitken, R. Alan,Al-Awadi, Nouria A.,Dawson, Graham,El-Dusouqi, Osman M.E.,Farrell, Dorcas M.M.,Kaul, Kamini,Kumar, Ajith
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p. 129 - 135
(2007/10/03)
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- Chemically Induced Anion Radical Cycloadditions: Intramolecular Cyclobutanation of Bis(enones) via Homogeneous Electron Transfer
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The first examples of anion radical cycloaddition induced by homogeneous electron transfer from chemical agents are described. Specifically, upon exposure to chrysene anion radical, bis(enone) substrates are found to engage in stereoselective intramolecular [2 + 2] cycloaddition. These studies, along with the corresponding electrochemically initiated reactions, provide insight into this fundamentally new pattern of reactivity and support the feasibility of expanding this novel reaction type. Copyright
- Yang, Jingkui,Felton, Greg A. N.,Bauld, Nathan L.,Krische, Michael J.
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p. 1634 - 1635
(2007/10/03)
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- 1,5-Diarylsubstituted 1,2,3-triazoles as potassium channel activators. VI
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As part of our program toward designing potassium channel openers, synthesis of a novel series of 1,5-diphenylsubstituted 1,2,3-triazoles, as potential activators of the large-conductance calcium-activated potassium channels (BK), as well as their vasorel
- Biagi, Giuliana,Calderone, Vincenzo,Giorgi, Irene,Livi, Oreste,Martinotti, Enrica,Martelli, Alma,Nardi, Antonio
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p. 397 - 404
(2007/10/03)
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