• Title/Summary/Keyword: Aryl aldehyde

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Asymmetric synthesis of (2S, 3R, 4E) 5-Aryl-4-pentene-1,3-diol-2-aminoueras

  • Im, C.U.;Kim, Y.H.;Jyung, M.L.;Lim, C.B.
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.237.1-237.1
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    • 2003
  • (2S 3R. 4E) 5-Aryl-4-pentene-1,3-diol-2-aminoueras had been synthesized for their cytotoxic activity. Pinene was oxidized with KMnO4 to give 2-hydroxy-3-pinanone. which treated with ethyl glycinate to yield iminoglycinate and then reacted with aldehyde derivatives and titanium enolate to afford 3-hydroxy aldol compounds. (omitted)

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Experimental and Theoretical Studies on the Tautomerism in 2-Aminopyridines and 2(1H)-Pyridinones: Synthesis of 2-Amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)pyridines and 4-Aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones

  • Davoodnia, Abolghasem;Attar, Paria;Morsali, Ali;Eshghi, Hossein;Tavakoli-Hoseini, Niloofar;Khadem, Shahriar
    • Bulletin of the Korean Chemical Society
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    • v.32 no.6
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    • pp.1873-1878
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    • 2011
  • Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4-dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate $[HO_3S(CH_2)_4MIM][HSO_4]$ (a Br${\o}$nsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level.

Silica Supported Tungstosilicic Acid as an Efficient and Reusable Catalyst for the One-Pot Synthesis of β-Acetamido Ketones via a Four-Component Condensation Reaction

  • Nasr-Esfahani, Masoud;Montazerozohori, Morteza;Gholampour, Tahere
    • Bulletin of the Korean Chemical Society
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    • v.31 no.12
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    • pp.3653-3657
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    • 2010
  • Silica supported tungstosilicic acid has been used as an effective catalyst for a modified Dakin-West one-pot, four-component condensation of an aryl aldehyde, an aryl ketone, acetyl chloride and acetonitrile for the synthesis of $\beta$-acetamido ketones. This catalytic system can act as an active, inexpensive, recoverable and recyclable catalyst. Some advantages of this system are short reaction times, good to excellent yields, easy work up and the ability to be carried out at the large scale reactions.

Ammonium Acetate: An Efficient Reagent for the One-pot Synthesis of 5-Aryl-7,8,13,14-tetrahydrodibenzo[a,i] phenanthridines, 2,4-Diaryl-6,7-benzo-3-azabicyclo[3.3.1]nonan-9-ones and α,α'-Bis(substituted benzylidene)cycloalkanones

  • Karthikeyan, Natesan Sundaramurthy;Sathiyanarayanan, Kulathu Iyer;Aravindan, Paduthapillai Gopal
    • Bulletin of the Korean Chemical Society
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    • v.30 no.11
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    • pp.2555-2558
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    • 2009
  • The condensation of cyclic ketone with aromatic aldehydes in the presence of ammonium acetate under ethanol media affords the corresponding 5-aryl-7,8,13,14-tetrahydrodibenzo[a,i]phenanthridine with excellent yield. This mild and efficient procedure with high yield is also applied to the synthesis of 2,4-diaryl-6,7-benzo-3-azabicyclo- [3.3.1]nonan-9-ones and ${\alpha},{\alpha}{$’-bis(substituted benzylidene)cycloalkanones.

Synthesis, Docking Study and In-vitro Evaluation of Anti-Tuberculosis Activity of Tri Substituted Imidazoles Containing Quinoline Moiety

  • Sahana, S.;Vijayakumar, G.R.;Sivakumar, R.;Sriram, D.;Saiprasad, D.V.
    • Journal of the Korean Chemical Society
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    • v.66 no.3
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    • pp.194-201
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    • 2022
  • A simple, efficient, and cost-effective method has been employed for the synthesis of 2,4,5-trisubstituted imidazole derivatives (3a-j) containing quinoline substituent at 2nd position. Title compounds were obtained by multicomponent reaction (MCR), involving aryl substituted 1,2-diketone, quinoline carbaldehyde and ammonium acetate in the presence of acetic acid solvent under mild reaction conditions. The newly synthesized quinoline containing imidazole derivatives were confirmed through FT-IR, 1H-NMR, 13C-NMR and mass spectral analysis. In-vitro microplate alamar blue assay (MABA) to determine the MIC (minimum inhibitory concentration) values against Mycobacterium tuberculosis H37Rv was performed for the synthesized compounds. The synthesized compounds exhibited activity against Mycobacterium tuberculosis and among which compounds, 3d, 3f and 3i showed good activity. The highest activity was showed with compound 3i. The anti-mycobacterial activity results are well correlated with the computational molecular docking analysis, which was performed for the synthesized compounds prior to the evaluation of the activity.

A Facile Solvent and Catalyst Free Synthesis of New Dihydro Pyrimidinones as Antimicrobial Agents

  • Hegde, Hemant;Ahn, Chuljin;Gaonkar, Santosh L.;Shetty, Nitinkumar S.
    • Journal of the Korean Chemical Society
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    • v.63 no.6
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    • pp.435-439
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    • 2019
  • An efficient one pot multicomponent synthesis of pyrimidinone derivatives of Biginelli type is described. 4-amino-6-aryl-pyrimidine-5-carbonitrile molecules were synthesized efficiently via three-component Biginelli-type condensation of aldehyde, malononitrile, and semicarbazone as urea substituent in the presence of a catalytic amount of PEG-400 as green medium under microwave irradiation. The reactions proceeded efficiently in the presence of microwave radiation to afford the desired products in good to excellent yields. Products have been confirmed by IR, and NMR spectral analysis. All the molecules were tested for their antimicrobial activity against E. coli, S. aureus, P. aeruginosa and C. tropicalis. Some of the compounds have shown moderate to good inhibition efficiency against both gram-positive and gram-negative bacteria. The potent activity was observed against the fungal species with minimum inhibition concentration 12.5 ㎍/mL.

Explorative and Mechanistic Studies of the Photooxygenation of Sulfides

  • Albini, Angelo;Bonesi, Sergio M.
    • Journal of Photoscience
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    • v.10 no.1
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    • pp.1-7
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    • 2003
  • The results of recent work on the dye-sensitized photooxygenation of sulfides is discussed. In the case of dialkyl sulfides, the weakly bonded adduct initially formed with singlet oxygen (the persulfoxide) decays unproductively unless protonation by an acid (an alcohol or a carboxylic acid) facilitates its conversion to the sulfoxide. The effect is proportional to the strength of the acid (eg., less than 0.1 % chloroacetic acid in benzene is sufficient for maximal efficiency) and corresponds to general acid catalysis, suggesting that protonation of the persulfoxide occurs. On the other hand, with sulfides possessing an activated hydrogen in ${\alpha}$ position (eg., benzyl and allyl sulfides), hydrogen transfer becomes an efficient process in aprotic media and yields a S-hydroperoxysulfoniumm ylide, possibly arising from a conformation of the persulfoxide that is different from the one protonated in the presence of acids. Calculations on some substituted sulfides support this hypothesis. This process, which leads to C-S bond fragmentation with formation of an aldehyde, may be viewed as a general method for the preparation of aryl and heteroaryl aldehydes. In this effort, mechanistic studies offered new hints on the structure of the intermediate persulfoxide.

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Synthesis of Certain Mercapto and Aminopyrimidine Derivatives as Potential Antimicrobial Agents

  • El-Kerdawy, M.M.;Eisa, H.M.;El-Emam, A.A.;Massoud, M.A.;Nasr, M.N.
    • Archives of Pharmacal Research
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    • v.13 no.2
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    • pp.142-146
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    • 1990
  • Reaction of ethyl 4-chloro-2-phenylpyrimidine-4-carboxylate (4) with 5-chloro-2-methylthiophenol or 3-aryl-4-phenyl-1, 2, 4-triazole-5 thiol yielded the corresponding thioethers (5) and (8a, b), respectively. Careful alkaline hydrolysis of (5) yielded the corresponding carboxylic acid (6). Reaction of (4) with p-aminoacetophenone yielded compound (10) which was reacted with certain aromatic aldehyde to afford the$\alpha,\beta$-unsaturated ketones (11a-d). Condensation of (11a-d) with malononitrile or phenylhydrazine yielded the 2-amino-3-cyanopyridines (12a-f) or the 2-pyrazolines (13a, b) respectively. Seven representative compounds were tested for their in vitro antimicrobial activity against some pathogenic micro-organisms, some of them were proved to be active.

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An Efficient Procedure for the Synthesis of Benzimidazoles Using H2O2/SiO2-FeCl3 System (H2O2/SiO2-FeCl3 계를 이용한 Benzimidazoles의 효율적인 합성)

  • Fazlinia, Abbas;Mosslemin, Mohammad Hossein;Sadoughi, Hesamaddin
    • Journal of the Korean Chemical Society
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    • v.54 no.5
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    • pp.579-581
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    • 2010
  • Solid silica supported ferric chloride ($SiO_2-FeCl_3$) catalyzed one-step synthesis of various benzimidazoles from o-phenylenediamine and aldehydes using $H_2O_2$ as the oxidant. The salient features of this method are simple and convenient procedure, easy purification and shorter reaction times.

Combinatory Effects of Benzene, Toluene and Xylene on the Induction of Rat Liver Microsomal Enzymes and Their Metabolites (흰쥐 간의 microsomal enzymes의 유도에 있어서 benzene, toluene과 xylene의 복합적인 영향과 그들의 대사산물)

  • 김기웅;박상신;김태균;문영한;장성근
    • Toxicological Research
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    • v.12 no.1
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    • pp.9-15
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    • 1996
  • We studied the effects of a single, combined and mixed exposure of benzene, toluene and xylene on the activities of rat liver microsomal AHH, ADH and ALDH, and the excretion of their metabolites in urine. The AHH activities of the rats treated in combination and mixture were slightly higher and/or similar to those rats treated with single solvent, while the reverse effects were observed for ADH and ALDH. Similar effects were observed when the metabolites were examined in urine (p < 0.01). These results suggest that each solvent might interJkre the induction and action of ADH and ALDH, and decrease the excretion of their metabolites into urine.

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