• 제목/요약/키워드: Carboxylic esters

검색결과 69건 처리시간 0.023초

혼성 Bivalent Ligand 퀴놀론 유도체의 합성 (Synthesis of Hybrid Bivalent Ligand Quinolone Derivatives)

  • 이상필;임채욱;김동순;임철부
    • 약학회지
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    • 제38권6호
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    • pp.664-672
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    • 1994
  • Eighteen new hybrid bivalent ligand quinolones that contain two different type of pharmacophores in a single molecule were prepared and evaluated for in viかo antibacterial activity. Hybrid bivalent ligands p-nitrobenzyloxycarbonyl quinolones were prepared by the treatment of active esters of succinyl fluoroquinolones with 1,7-disubstituted fluoroquinolone carboxylic acids in DMF. Eighteen final quinolone carboxylic acids were obtained by the reduction of compounds $25{\sim}42$ with hydrogen in the presence of 10% Pd-C. Among these derivatives, compound[56] showed the most potent antibacterial activity against a wide range of microoranisms.

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Dynamic Kinetic Resolution of α-Bromo Carboxylic Acid Derivatives in Asymmetric Nucleophilic Substitution with Chiral α-Amino Esters

  • Chang, Ji-Yeon;Shin, Eun-Kyoung;Kim, Hyun-Jung;Kim, Yong-Tae;Park, Yong-Sun
    • Bulletin of the Korean Chemical Society
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    • 제26권6호
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    • pp.989-992
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    • 2005
  • Dynamic kinetic resolution of $\alpha$-bromo carboxylic acid derivatives in nucleophilic substitution with chiral $\alpha$-amino ester nucleophiles in the presence of TBAI and DIEA has been investigated for stereoselective syntheses of 1,1'-iminodicarboxylic acid derivatives. Nucleophilic substitutions with various chiral $\alpha$-amino esters gave iminodiacetates 2-8 with stereoselectivities up to 87 : 13 dr. Also, the reactions of N-($\alpha$-bromo-$\alpha$-phenylacetyl)-L-alanine methyl ester with L-alanine, D-alanine and glycine methyl ester nucleophiles afforded N-carboxyalkyl dipeptide analogues 10-12 up to 90 : 10 dr.

Novel Synthetic Reactions Using 1-Fluoro-2, 4, 6-trinitrobenzene. An Efficient Direct Esterification Method

  • Kim Sunggak;Ahn Kyo Han;Yang Sungbong
    • Bulletin of the Korean Chemical Society
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    • 제3권2호
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    • pp.70-76
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    • 1982
  • Synthetic utility of 1-fluoro-2,4,6-trinitrobenzene (FTNB) as a condensing agent was investigated. The use of FTNB and DMAP was found to be very effective for direct esterification of carboxylic acids with alcohols or thiols. However, this system was not very effective for macrolactonization. Reaction of 2,4,6-trinitrophenyl esters with several nucleophiles was investigated briefly. Plausible reaction mechanisms of esterification are presented. It seems that the reaction proceeds via the intermediacy of 2,4,6-trinitrophenyl esters by initial formation of 2',4',6'-trinitrophenyl-4-dimethylaminopyridinium salt from which the trinitrophenyl group is transferred to the carboxylic acid.

Chiral Derivatization of Hydroxycarboxylic Acids Using 2,4,6-Trichlorobenzoyl Chloride as a Highly Efficient Regioselective Esterification Reagent for Gas Chromatography-Mass Spectrometry

  • Park, Jeong Hyeok;Han, Sang Yun
    • Mass Spectrometry Letters
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    • 제11권4호
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    • pp.103-107
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    • 2020
  • We report the application of 2,4,6-trichlorobenzoyl chloride (often referred to as Yamaguchi esterification reagent) for the selective derivatization of the carboxylic group for GC-MS with the sample preparation method optimized for GC-MS analysis. The reagent was shown to be capable of selectively turning the carboxylic group into a reaction center, i.e., anhydride, of which the further reaction was directed to a near complete formation of required esters by unique steric and electronic effects of the reagent. Using the developed method, the chiral separation of hydroxycarboxylic acids by GC-MS using non-chiral columns was successfully demonstrated.

Convenient Synthesies of Carboxylic Esters and Thiol Esters Using Acid Chlorides and Zinc Chloride

  • Kim, Sung-Gak;Lee, Won-Jae;Lee, Jae-ln
    • Bulletin of the Korean Chemical Society
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    • 제5권5호
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    • pp.187-190
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    • 1984
  • Reaction of acid chlorides with primary alcohols, secondary alcohols, and aryl alcohols in the presence of a catalytic amount of zinc chloride gave the corresponding esters in high yields, whereas the reaction with tertiary alcohols failed to give the esters due to the fast solvolytic reactions of tertiary alcohols with hydrogen chloride generated from the reaction. The use of molecular sieves as a scavenger for hydrogen chloride was found to be moderately effective in the reaction of mesitoyl chloride with tertiary alcohols. Reaction of acid chlorides with thiols in the presence of zinc chloride in acetonitrile proceeded cleanly, yielding the corresponding thiol esters in high yields.