• Title/Summary/Keyword: Aldehyde condensation

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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 and Absorption Spectral Properties of Bis-methine Dyes Exemplified by 2,5-Bis-arylidene-1-dicyanomethylene-cyclopentanes

  • Asiri, Abdullah Mohamed
    • Bulletin of the Korean Chemical Society
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    • v.24 no.4
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    • pp.426-430
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    • 2003
  • A range of methine dyes has been synthesized by condensation of highly electronegative active methylene compound dicyanomethylenecyclopentane derived from cyclopentanone with the formyl group of substituted benzaldehydes. The electronic absorption spectroscopic properties of the dyes were investigated. In general, substituents on the aromatic aldehyde moiety have a significant effect on the visible absorption maxima of the dyes; increasing the solvent polarity also showed a pronounced effect on the absorption maxima.

Synthesis of Adenosine and Uridine Analogues Containing Conjugated Diene (공액 이중 결합을 갖는 Adenosine과 Uridine 유사체의 합성)

  • Ro, Bong Oh
    • Journal of the Korean Chemical Society
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    • v.45 no.4
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    • pp.312-317
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    • 2001
  • 7'-Aldehyde-nucleosides analogue (2a, 2c) were synthesized from 6-N-benzoyl-2',3'-O-isopropylideneadenosine and uridine. The condensation of 2 with ethoxycarbonylmethylene Wittig reagent produced the adenosine and uridine analogues containing extended conjugated diene and ethoxycarbonyl group, ethyl-1',5',6',7',8'-pentadeoxy-1'-(adenin-9-yl)-$\beta$-D-ribo-nona-5'(E),7'(E)-dienofuranuronate (4b) and ethyl-1'. 5',6',7',8'-pentadeoxy-1'-(uracil-1-yl)-$\beta$-D-ribo-nona-5'(E),7'-(E)-dienofuranuronate (4c). 9-[8',8'-dibromo-5',6',7',8' -tetradeoxy-$\beta$-D-ribo-octa-5'(E),7'(E)-diene]nucleosides (6b, 6c) were also prepared from 2 with similar method.

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Synthesis and Phytotoxic Activities of (8S, 9S, 11R)-(-)-Monocerin and (9S, 11R)-(+)-Fusarentin 4, 5-dimethyl ether ((8S, 9S, 11R)-(-)-Monocerin and (9S, 11R)-(+)-Fusarentin 4, 5-dimethyl ether의 합성과 생리활성)

  • Ko, Byoung-Seob
    • Applied Biological Chemistry
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    • v.37 no.5
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    • pp.402-408
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    • 1994
  • For the examination of the role of monocerin(1) on the biological activity, (8S, 9S, 11R)-(-)-monocerin(20) and (9S, 11R)-(+)-fusarentin 4, 5-dimethyl ether(19) were synthesized by a condensation of the benzylic anion of ethyl 2, 3, 4-trimethoxy-6-methylbenzoate(16) with modifyed (R)-ethyl 3-hydroxyhexanoate (9). In a key step, bioreduction with active dried baker's yeast in organic solvent system was employed to get a chiral aldehyde 12. Their phytotoxic activities were tested on rice seedlings and lettuce seeds.

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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.

Synthesis and Antimicrobial Activity of Novel Tetrahydrobenzothienopyrimidines

  • Amal Abdel Haleem Mohamed Eissa;Ashraf Ahmed Moneer
    • Archives of Pharmacal Research
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    • v.27 no.9
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    • pp.885-892
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    • 2004
  • Due to the rapidly growing number of resistant strains of bacteria, the search for antibacterial agents with new modes of action will always remain an important and challenging task. Thus, the reaction of 2-substituted or. unsubstituted-4-(4-acetylanilino)-5,6,7,8-terahydrobenzo[b] thieno[2,3-d]pyrimidine derivatives 1-3 with the hydrazine derivatives, semi and / or thiosemi-carbazides, provided the corresponding hydrazones 4-6 and semi and/or thiosemicarbazones 7-9. Claisen-Schmidt condensation of compounds 1 or 2 with the appropriate aldehyde yielded the chalcones 10, 11 which, when treated with hydroxylamine hydrochloride gave rise to the isoxazoline-containing compounds 12, 13. Furthermore, reacting the respective chalcones 10, 11 with different hydrazines, urea and/or thiourea, furnished compounds 14, 15, 16, and 17 respectively. Representative compounds were tested for their antimicrobial activity against Candida Albicans and certain gram-positive and gram-negative bacteria. Their MICs were then determined. Compound 15e, showed a broad spectrum of activity while most of the other com-pounds showed varying antimicrobial activity.

Highly Diastereoselective Aldol-Type Reaction Using 3-Acetylthiazolidine-2-thione (3-아세틸티아졸리딘-2-티온을 이용한 입체선택적인 알돌-축합반응)

  • Tae Myeong Jeong;Ki Hun Park
    • Journal of the Korean Chemical Society
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    • v.33 no.4
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    • pp.426-430
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    • 1989
  • Amino alcohol-derived thiazolidinethiones [4-(S)-IPTT, 4(S)-ETT] serve as efficient chiral auxiliary in tin medicated aldol condensation. A highly enantioselective aldol-type reaction forming various ${\beta}$-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehyde is achieved via divalent tin enolate. The other advantages of these chiral auxiliaries were the ease of removal by methanolysis.

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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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