• Title/Summary/Keyword: Diethyl malonate

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Synthesis of $(\pm)-\alpha-Hydroxy-\alpha$-(p-Chlorobiphenyl)Acetic Acid and its Resolution ($(\pm)-\alpha-Hydroxy-\alpha$-(p-Chlorobiphenyl)acetic acid 합성과 분할)

  • 권순경
    • YAKHAK HOEJI
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    • v.39 no.4
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    • pp.433-437
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    • 1995
  • Optically pure(-)-and (+)-$\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)acetic acids were prepared. The racemate was synthesized through three steps. By condensation of p-cnorobiphenyl with diethyl ketomalonate in the presence of SnCl$_{4}$, diethyl $\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)malonate (1) was formed and subsequently ($\pm$)-$\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)acetic acid (3) was obtained through hydrolysis and decarboxylation. For the separation of the racemate the classical resolution method, derivatization of a racemate by reaction with an optically pure compound was employed. In this case the optically pure compound were [R]-(+)-$\alpha$-methylbenzylamine and [S]-(-)-$\alpha$-methylbenzylamine. Diastereomeric salts between acids and bases could be easily separated by crystallization in absolute ethanol.

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Synthesis of Heterocyclic Quinones Containing Bridgehead Nitrogen Atom from 2-Aminonaphtho[2,3-d]thiazole-4,9-dione

  • Fandy, Ragab F.
    • Archives of Pharmacal Research
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    • v.23 no.5
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    • pp.446-449
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    • 2000
  • Imidazonaphthothiazole derivatives 3∼6 were prepared by treatment of 2-aminonaphtho[2,3-d]-thiazole-4,9-dione(1) with phenacyl bromide, chloroacetic acid, diethyl oxalate and 2,3-dichloroquinoxaline respectively. The reaction of 1 with ethyl acrylate, ethyl acetoacetate and diethyl malonate gave the corresponding naphthothiazolopyrimidine derivatives 8∼11.

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Solvent-Free Michael Addition Between EMME and Secondary Amine under Focused Microwave Irradiation

  • Kim, Ki-Won;Lee, Hee-Jung;Jo, Jeong-Im;Kwon, Tae-Woo
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1155-1158
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    • 2010
  • Microwave-assisted Michael reaction between EMME and various amines such as diphenylamine, 4-methyl-N-phenylbenzenamine, N-phenylnaphthalen-1-amine, dihexylamine, diisopropylamine, and 4-nitrobenzenamine were described. Solvent-free conditions on alumina as solid support in the presence of $K_2CO_3$ catalysts gave moderate to good yields (55 - 93%) of diethylmalonate analogues having enamine moieties under focused microwave irradiation.

Surface Properties and the Catalytic Activity of Amorphous Iron Aluminophosphates: Effect of Fe Loading (비정질 인산알루미늄 철의 표면 성질 및 촉매 특성: 함유된 철의 양에 의한 효과)

  • Vijayasankar, A.V.;Aniz, C.U.;Nagaraju, N.
    • Journal of the Korean Chemical Society
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    • v.54 no.1
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    • pp.131-136
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    • 2010
  • Iron aluminophosphates (FeAlP) with different percentage of iron were synthesized and characterized for their surface and bulk properties. The catalytic activity was determined in the transesterification of diethyl malonate with benzyl alcohol. Benzyl ethylmalonate and dibenzyl malonate were obtained as the only products. FeAlP with 0.025 mole % of iron was found to be distinctly different in its textural and catalytic properties. Formation of diester was found to be favored by the acid sites of intermediate strength. The presence of hydrated alumina and the polycondensed phosphates in the materials reduced the catalytic activity of iron aluminophosphates in transesterification reaction.

Convenient Synthesis of Optically Pure α-Mono and α,α-Disubstituted β-Amino Acids

  • Lee, Hyun-Soo;Park, Jung-Dae;Kim, Dong-H.
    • Bulletin of the Korean Chemical Society
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    • v.24 no.4
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    • pp.467-472
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    • 2003
  • Optically pure α-mono- and α, α-disubstituted β-amino acids were conveniently prepared in four steps and in 27-40% overall yields from the correspondingly substituted racemic β-hydroxy acids that can be readily obtained from diethyl malonate. In the synthesis, (S)-phenylethylamine has been used as a resolving agent and as a source of the amino group in the β-amino acids.

Thienobenzothiopyranones 111-New 4H-thieno[2,3-b][1]benzothiopyran-4-ones Carrying Different Heterocyclic Moieties of Expected Pharmacological Interest

  • El-Subbagh, H.I.;El-Emam, A.A.;El-Ashmawy, M.B.;Shehata, I.A.
    • Archives of Pharmacal Research
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    • v.13 no.1
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    • pp.24-27
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    • 1990
  • Reaction of 2-formyl-4H-thieno [2, 3-b] benzothiopyran-4-one (1) with different heterocyclic amines afforded the corresponding Schiff's bases (2-4). Diethyl malonate, ethyl cyanoacetate and malononitrile were reached with 1 to afford compounds 5, 7 and 8, respectively. Compound 5 was cyclized to the pyrazolidin-3, 4-dione (6) by the action of hydrazine hydrate, whereas compound 7 was utilized for the synthesis of the thiazolin-4 one derivatives (9-13).

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Synthesis of New ${\alpha}$-Amidoketenes Using Malonyl Dihalide (Malonyl Dihalide를 이용한 새로운 ${\alpha}$-Amidoketenes의 합성)

  • Oh, Mi-Jung;Park, Myung-Sook
    • YAKHAK HOEJI
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    • v.55 no.2
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    • pp.127-130
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    • 2011
  • We synthesized new ${\alpha}$-amidoketenes using dehydrochlorination from anilines, triethylamine and malonyl dichloride under $0^{\circ}C$. The utility of ketenes in both laboratory and industrial practice was quickly recognized, and these species have been extensively utilized, including as pharmaceutical intermediates and anti-cancer agents. All synthetic process from anilines to ${\alpha}$-amidoketenes could be carried out by one-pot reaction. Synthetic ketenes 2a~f were identified using NMR and IR spectrum. Formation of ketenes was undertaken with dropping of malonyl dichloride at $0^{\circ}C$ in methylene chloride for 0.5~4 h. Using malonyl dichloride was better than using diethyl malonate as a synthetic reagents for the ketenes.

Potassium Pentane-1,3,3,5-tetracarboxylate Draw Solute Synthesis and Application of Forward Osmosis Process (Potassium Pentane-1,3,3,5-tetracarboxylate 유도용질 합성 및 이를 이용한 정삼투 공정 응용)

  • Lee, Hye-Jin;Choi, Jin-Il;Kwon, Sei;Kim, In-Chul
    • Membrane Journal
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    • v.29 no.2
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    • pp.111-121
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    • 2019
  • An organic citrate series draw solute was synthesized using diethyl malonate for forward osmosis. The structure of the final compound potassium pentane-1,3,3,5-tetracarboxylate was confirmed by $^1H-NMR$ and $^{13}C-NMR$ analysis. Osmotic pressure, solubility, water permeability and reverse salt flux were measured for the properties of the draw solute. Forward osmosis results showed that the draw solute exhibited higher water flux than other draw solutes of trisodium citrate and tripotassium citrate. Reverse salt flux of all the organic daw solutes was much lower than that of NaCl. The osmotic pressure of the synthesized draw solute was 25% lower than that of NaCl. The solubility of the draw solute was 317 g/ 100 g water, which is 8.8 times higher than that of NaCl. A commercialized nanofiltration membrane was used for the recovery of the draw solute. The draw solute could be effectively recovered at low pressure.