• Title/Summary/Keyword: Acetophenone

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Synthesis of Novel Carbovir Analogue

  • Kim, Ai-hong;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.27 no.7
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    • pp.976-980
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    • 2006
  • The synthesis of 4'-phenyl and 1'-methyl doubly branched carbocyclic nucleoside was accomplished from 2-hydroxy acetophenone. The 4'-phenyl group was installed via a [3,3]-sigmatropic rearrangement reaction, and the carbonyl addition of methylmagnesium bromide was used to introduce the 1'-methyl group. Cyclization of divinyl 9 was performed using $2^{nd}$ generation Grubbs catalyst. The coupling of cyclopentenol 12$\alpha$ with 6-chloropurine by Mitsunobu reaction and desilylation was used to synthesize the target nucleoside 15.

A Study on the Knoevenagel Reaction of Fluorinated Carbonyl Compounds (含弗素有機 Carbonyl化合物의 Knoevenagel反應에 關한 硏究)

  • You Sun Kim
    • Journal of the Korean Chemical Society
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    • v.7 no.1
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    • pp.85-90
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    • 1963
  • The Knoevenagel reaction of fluorinated carbonyl compounds, 1,1,1-trifluoro-propanone-2-heptafluoro-butyraldehyde, 1,3-dichloro-1,1,3,3-tetrafluoro-acetone, tetradecafluoro-heptanone-4 and 2,2,2-trifluoro-acetophenone yielded fluorinated ${\beta},{\beta}$-dialkyl-${\beta}$-hydroxy acids. Dehydration of the acids do not give the olefinic acid in the case of the perfluorinated system and gave a lactone. From the consideration of electronic and steric effects a mechanismic path of the reaction via a carbanion intermediate was proposed for the reaction. Preparation of related derivatives are also described.

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Synthesis of 4'α-C Phenyl-Branched Carbocyclic Nucleoside Using Ring-Closing Metathesis

  • Hong, Joon-Hee;Ko, Ok-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.24 no.9
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    • pp.1289-1292
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    • 2003
  • An efficient synthetic route for preparing novel $4'{\alpha}$-C phenyl branched carbocyclic nucleoside is described. The installation of phenyl group at the $4'$-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) beginning from simple ketone such as 2-hydroxy acetophenone.

Acetophenones from the Roots of Cynanchum wilfordii HEMSLEY

  • Hwang, Bang-Yeon;Kim, Young-Ho;Ro, Jai-Seup;Lee, Kyong-Soon;Lee, Jung-Joon
    • Archives of Pharmacal Research
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    • v.22 no.1
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    • pp.72-74
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    • 1999
  • Two acetophenones, cynandione A (1) and cynanchone A (2), were isolated from the roots of Cynanchum wilfordii. Their structures were identified by comparison of their physicochemical and spectral data with reported values.

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First Total Synthesis of Prorepensin with a Bis-Geranylated Chalcone

  • Jung, Eun-Mi;Lee, Yong-Rok
    • Bulletin of the Korean Chemical Society
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    • v.30 no.11
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    • pp.2563-2566
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    • 2009
  • The first total synthesis of naturally occurring prorepensin with a bis-geranylated chalcone has been achieved by a convergent sequence. The key strategy involved in the synthesis of prorepensin was chalcone formation by aldol condensation of the corresponding geranylated acetophenone with geranylated benzaldehyde.

Medium effects on the H-Atom Abstraction and Silyl-Transfer Photoreactions of Silylalkyl Ketones

  • Oh, Sun-Wha
    • Journal of Photoscience
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    • v.12 no.1
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    • pp.47-50
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    • 2005
  • Mediumeffects have been explored on the competitive H-atom abstraction and SET-promoted, silyl-transfer reactions of excited states of silylalkyl-substituted phenyl ketones. The chemical selectivities of photochemical reactions of silylalkyl phenyl ketones appear to depend on medium polarity, medium silophilicity, added metal cation and alkyl length. Irradiations of silylalkylketones in aqueous solvent system and in presence of metal cation such as $Li^+$ and $Mg^{+2} $lead to formation of acetophenone predominantly by the sequential SET-silyl transfer route.

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Selective Reduction of Oximes to N-Monosubstituted Hydroxylamines with Lithium Borohydride

  • Cho, Byung-Tae;Seong, See-Yearl
    • Bulletin of the Korean Chemical Society
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    • v.9 no.5
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    • pp.322-324
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    • 1988
  • Selective reduction of aldoximes and ketoximes with lithium borohydride in tetrahydrofuran was investigated. Thus, aldoximes and cyclic ketoximes such as hexanaldoxime, heptanaldoxime, cyclopentanone oxime and cyclohexanone oxime were reduced smoothly to the corresponding N-monosubstituted hydroxylamines at room temperature in 65-93% yield. The reduction of alicyclic ketoxime was very slow, requiring somewhat high reaction temperature ($65^{\circ}C$) for the complete reduction to give the hydroxnylamines. The reduction of aromatic oximes such as benzaldoxime and acetophenone oxime was very sluggish, giving a mixture of the corresponding hydroxylamines and amines at $65^{\circ}C$.

Synthesis of 2-phenyl-1,8-naphthyridin-4-ones

  • Im, Cha-Euk;Park, Sang-Min;Kim, Yong-Hyun;Chung, Mi-Ryang;Yim, Chul-Bu
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.175.3-175.3
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    • 2003
  • 2-Phenyl-1, 8-naphthyridin-4-ones had been synthesized for their cytotoxic activity. Substituted acetophenone was treated with NaH and diethyl carbonate to give ethyl benzoylacetates, which was reacted with substituted 2-aminopyridine and PPA to yield 2-phenylpyridopyrimidine-4-ones. These compounds was heated at $350^\times$C in liquid paraffin to afford final compounds, 2-phenyl-1 , 8-naphthyridin-4-ones.

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Synthesis of Some Pyridine and Dihydropyridine Derivatives from 7-Hydroxy-8-Methoxyl-2-Oxo-2H-1-Benzopyran-6-Carboxaldehyde

  • El-Diwani, Hoda I.
    • Archives of Pharmacal Research
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    • v.18 no.1
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    • pp.27-30
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    • 1995
  • The Hantzsh reaction of 7-hydroxy-8-methoxy-2-oxo-2H-benzopyran-6-carboxaldehyde (1) with ethyl acetoacetate and ammonia yields the dihydropyridine derivative 2 together with the pyridine derivative 3 and the eight membred ring derivative 4. Reaction of 1 with ethyl cyanoacetate and malononitrile gives the iminodicoumarin derivatives 5 and 6 respectiely. The latter compound was reacted with butan-2-one and acetophenone to produce the Michael adduct 71, b and the 2-aminopyridine derivatives 8a, b.

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Synthesis of Hydrazone Derivatives of 4-(2-Chloroethyl) semicarbazide : A New Class of Cytotoxic Agents (4-(2-Chloroethyl) semicarbazide의 히드라존 유도체 합성:새로운 종류의 세포독성요법제)

  • El-Sabbagh, O.I.;El-Sadek, M.E.;Aboukull, M.E.;Shallal, H.M.
    • Journal of the Korean Chemical Society
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    • v.53 no.1
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    • pp.34-41
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    • 2009
  • A new series of hydrazone derivatives were synthesized from 4-(2-chloroethyl)semicarbazide and their antiproliferative activity against human brain (U251) and liver (Hepg2) carcinoma cell lines were evaluated. The hydrazone compounds are benzaldehyde (2a-2g), acetophenone (3a-3f), and 3-formylindole derivatives (4a-4d). Among the acetophenone derivatives, 3e (p-methoxy substituted) and 3f (p-nitro substituted) showed the highest cytotoxic activity against Hepg2 cell line (I$C_{50}$ = 6 and 8 $\mu$g/ml, respectively). Among the 3-formylindole derivatives, 4a (hydrazone of 3-formylindole itself) showed a pronounced cytotoxic activity against both U251 (I$C_{50}$ = 21 $\mu$g/ml) and Hepg2 (I$C_{50}$ = 7 $\mu$g/ml).