• Title/Summary/Keyword: Oxalyl Chloride

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DMSO-Oxalyl Chloride for the Oxidation of Carbohydrates (DMSO-Oxalyl Chloride에 의한 당의 산화)

  • 천문우
    • YAKHAK HOEJI
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    • v.27 no.2
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    • pp.181-184
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    • 1983
  • DMSO-oxalyl chloride at low temperature in methylene chloride reacted with isolated secondary hydroxyl groups in some monosaccharides to give alkoxysulfonium salts, convertible to carbonyls in high yields upon addition of triethylamine. And 1, 2:5, 6-di-O-isopropylidene-.alpha.- D-allofuranose which is the key intermediate in the synthesis of 3-O-acetyl-5-O-benzoyl- 2-deoxy-2- fluoro-D-arabinofuranosyl bromide, was also obtained by oxidizing 1, 2:5, 6-di-O-isopropylidene-.alpha.- D-glucofuranose with the oxidizing reagent, followed by reduction with sodium borohydride.

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Syntheses of New Lactones Containing Phenyl or Methyl Groups (페닐기 및 메틸기를 포함하는 새로운 lactone의 합성)

  • Chang, Seung Hyun;Moon, Sang Chil;Kim, Hak Hee;Lee, Kap Duk;Chung, Kwang Bo
    • Applied Chemistry for Engineering
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    • v.9 no.6
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    • pp.842-845
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    • 1998
  • Four new lactones and one dibenzo crown ether were synthesized by reaction of dihydroxy compound with oxalyl chloride and with ${\alpha}$,${\omega}$-dibromo compound, respectively. 5,6,11,12-Tetracarbonyl-2,2,3,3,8,8,9,9-octaphenyl-1,4,7,10-tetraoxacyclodode- cane(1), 5,6,11,12-tetracarbonyl-2,2,3,3,8,8,9,9-octamethyl-1,4,7,10-tetraoxacyclododecane(2), 7,8,15,16-tetracarbonyl-1,6,9,14-tetraoxacylclohexadecane(3), and 5,6,11,12-tetracarbonyl- 2,3,8,9- tetraphenyl-1,4,7,10-tetraoxacyclododecane(4) were prepared by reaction of oxalyl chloride with benzopinacol, pinacol, 2,2'-dihydroxybiphenyl and hydrobenzoin, respectively, in the presence of pyridine. Dibenzo-13-crown-4 (5) was obtained by reaction of catechol with 1,3-dibromopropane/1,2-dibromoethane.

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Synthesis of Several Diester Group-Containing Calix[4]arenes

  • 남계준;양용식;전종철;최용국
    • Bulletin of the Korean Chemical Society
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    • v.17 no.6
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    • pp.502-506
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    • 1996
  • Several ester group-containing calix[4]arenes were synthesized by the reaction of calix[4]arene and various acyl chlorides. Two or four ethyl succinyl units could be introduced into the calix[4]arene lower rim depending on the reaction conditions. But the mixture of three and four ethyl malonyl substituted calix[4]arenes were obtained and only three ethyl oxalyl units were introduced at the lower rim of calix[4]arene. Interestingly when calix[4]arene was treated with ethyl oxalyl chloride in the presence of aluminum chloride, two ethyl oxalyl units were introduced at the upper rim of calix[4]arene. The conformation of those ester-containing calix[4]arenes was presented based on the 1H and 13C NMR spectra.

Synthesis of the New Saccharin Derivatives Containing Imidazolidine-2,4,5-trione or 2-Thio-imidazolidine-4, 5-dione Group (Imidazolidine-2,4,5-trione 혹은 2-thio-imidazolidine-4,5-dione기를 포함하는 새로운 saccharin 유도체의 합성)

  • Jung, Dai-Il;Byun, Suk-In;Kim, Yun-Young;Kim, Young-Hwan;Lee, Do-Hun;Song, Hyun-Ae;Lee, Yong-Gyun;Park, Yu-Mi;Choi, Soon-Kyu;Han, Jung-Tae
    • Journal of Life Science
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    • v.14 no.2
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    • pp.351-355
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    • 2004
  • Saccharin derivatives were synthesized by means of 4 reaction steps involved the reaction of 1-methylurea (or 1-methylthiourea) and oxalyl chloride. 1-Alkyl(or phenyl)-3-(1,1,3-trioxo-1,3-dihydro-1$^{6}$ -benzo[d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-trione 5 and 1-alkyl(or phenyl)-2-thioxo- 3-(1,1,3-trioxo-1,3-dihydro-1$^{6}$ -benzo-[d]isothiazol-2-ylmethyl)-imidazolidine-4,5-dione 12 were obtained by means of 4 reaction steps involved the reaction of 1-methyl-urea(or 1-methylthiourea) and oxalyl chloride.

Studies on the Synthesis of Etodolac Derivatives as Potential Anti-inflammatory Agents (항염증제인 Etodolac 유도체의 합성에 관한 연구)

  • Cho, Hoon;Chung, Yong Seog;Jang, Hang Dong;Ryu, Seong Ryual
    • Applied Chemistry for Engineering
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    • v.10 no.1
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    • pp.135-137
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    • 1999
  • For the synthesis of new anti-inflammatory agents as indol derivatives, we have synthesized ${\alpha}$-benzoyl-1-ethyl-1,3,4,9-tetrahydro-8-ethyl-9-(N-benzoyl)pyrano[3,4-b]indole-1-acetic acid methyl ester. It was a new method for ${\alpha}$-substituted etodolac carboxylic acid. The synthetic process was composed of four steps, and 7-ethylindole and oxalyl chloride were used as starting materials. The third step, cyclization was carried out by addition of borontrifluoride diethyl etherate in 66% yield. The step of reduction and cyclization were simplified successfully. The final product, ${\alpha}$-benzoyl-1-ethyl-1,3,4,9-tetrahydro-8-ethyl-9-(N-benzoyl)pyrano[3,4-b]indole-1-acetic acid methyl ester was obtained in 66% yield by the reaction of methyl 1,8-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetate (etodollic acid methyl ester) and benzoyl chloride.

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Synthesis of 8-Methyl-8,14-cycloberbine Derivatives (8-Methyl-8,14-cycloberbine 유도체 합성)

  • Hwang, Soon-Ho;Kim, Jae-Hyun;Yim, Hyung-Yub;Kim, Sin-Kyu
    • YAKHAK HOEJI
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    • v.38 no.4
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    • pp.451-454
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    • 1994
  • In accordance with reported references, 8-methyl-8,14-cycloberbine was derived from berberinephenolbetaine. On acidic treatment the 8-methyl-8,14-cycloberbines were converted easily to the compounds $1{\sim}7$ in good yields. We developed a novel method for a synthesis of the C8-N bond adduct compounds 8 and 9 from 8-methyl-8,14-cycloberbine by treatment with oxalyl chloride, and 1,3-dichloroaceton.

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Synthesis of 2-Substituted Flavone Derivatives (2-치환 플라본 유도체의 합성)

  • Dan, On-Wha;Kim, Su-Jin;Im, Chae-Uk
    • YAKHAK HOEJI
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    • v.50 no.6
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    • pp.398-402
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    • 2006
  • Flavone was found to inhibit tyrosinase and reduce synthesis of melanin to show skin-lightening effect. With the hope of identifying skin-lightening flavones, we synthesized flavone analogs. Substituted benzoic acids (1) were treated with oxalyl chloride in DMF to yield benzoyl chlorides (2), which were reacted with 2-hydroxyacetophenones (3) to afford 2-benzoyloxyacetophenones (4). These acetophenones (4) were converted into 1,3-diketones (5) with base and then treated with acid to give flavone derivatives (6).

Synthesis and Activity Evaluation of Imidazolidinetrionylsaccharin Derivatives (Imidazolidinetrionylsaccharin 유도체의 합성 및 활성평가)

  • Jung, Dai-Il;Kim, Yun-Young;Kim, Young-Hwan;Lee, Do-Hun;Lee, Gi-Hye;Shin, Yeo-Ju;Kim, Yun-Hye;Byun, Suk-In;Han, Jung-Tae
    • Journal of Life Science
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    • v.13 no.1
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    • pp.54-58
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    • 2003
  • 1-Methyl-3-(1,1,3-trioxo-1,3-dihydro-1λ$^6$-benzo[d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-triones 5a, 1-ethy1-3-(1,1,3-trioxo-1,3-dihydro-lλ$^6$/-benzo[d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-triones 5b 1-phenyl-3-(1,1,3-trioxo-1,3-dihydro-1λ$^6$-benzo [d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-triones 5c were obtained by means of 4 reaction steps involved the reaction of 1-methyl-urea and oxalyl chloride. Biological tests(Plant Response Screening Result, Insect Primary Screening Result and Fungicide Primary Screening Result) of synthesized sacccarin derivatives were executed.

Synthesis and Small Animal Brain PET Study of a Serotonin Receptor Radiotracer, 18F-Mefway (세로토닌 5-HT1A수용체 방사성 추적자 18F-Mefway의 합성과 소동물 뇌 PET 연구)

  • Ahn, Sung-Min;Hong, Tae-Kee;Ryu, Young-Hoon;Choi, Jae-Yong;Kim, Sung-Chul
    • The Journal of the Korea Contents Association
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    • v.9 no.11
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    • pp.262-270
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    • 2009
  • $^{18}F$-mefway has been developed as radioligand for serotonin receptor 5-$HT_{1A}$. The object of this study was to obtain the mefway precursor with the higher yield than previous method and to identify whether $^{18}F$-mefway can bind to 5-$HT_{1A}$ or not. from microPET imaging of small animal brain. Precursor was prepared by a modification of the reported procedure then [$^{18}F$] labeling was performed by adding $^{18}F$ ion at $130^{\circ}C$ in the hot cell for 30min. After purification of reaction mixture using alumina Sep-pak and HPLC, microPET images of small animal brain were determined. The chemical yield of precursor was increased from 9% to 34% using oxalyl chloride and LAH/diethylether. We synthesized a precursor which was successfully labeled with no-carrier-added $^{18}F$-by new synthetic route. This research suggest that $^{18}F$-mefway will be used a radiopharmaceutical for evaluation of central nerve system disorder as imaging a gent for 5-$HT_{1A}$ receptor.