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      Malonyl Dihalide를 이용한 새로운 α-Amidoketenes의 합성 = Synthesis of New α-Amidoketenes Using Malonyl Dihalide

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      https://www.riss.kr/link?id=A100576155

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      다국어 초록 (Multilingual Abstract)

      We synthesized new α-amidoketenes using dehydrochlorination from anilines, triethylamine and malonyl dichloride under 0oC. The utility of ketenes in both laboratory and industrial practice was quickly recognized, and these species have been extensiv...

      We synthesized new α-amidoketenes using dehydrochlorination from anilines, triethylamine and malonyl
      dichloride under 0oC. 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 α-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 0oC in methylene chloride for 0.5~4 h. Using malonyl dichloride was better than using diethyl malonate as a synthetic reagents for the ketenes.

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      참고문헌 (Reference)

      1 Yan, S. J., "Solvent-free, microwave assisted synthesis of polyhalo heterocyclic ketene aminals as novel anti-cancer agents" 20 : 48-, 2010

      2 Sheibani, H, "Mesoionic 1,3- oxazinium olates. Rearrangement to acylketenes and 3- azabicyclo[3.1.1]heptanetriones" 70 : 5859-, 2005

      3 Tidwell, T. T, "Ketenes, 2nd" John Wiley & Sons, Inc 1-, 2006

      4 Taggi, A. E, "Generation of ketenes from acid chlorides using NaH/Crown ether shuttle-deprotonation for use in asymmetric catalysis" 4 : 627-, 2002

      5 Finnerty, J, "Facile 1,3-Shift of chlorine in a Chlorocarbonylketene" 120 : 1701-, 1998

      6 Bornemann, H, "Energy profiles for ketene cyclizations. Interconversion of 1,3-oxazin-6-ones mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products" 70 : 5862-, 2005

      7 Fu, G, "Enantioselective nucleophilic catalysis with "Planar- Chiral" heterocycles" 33 : 412-, 2000

      8 Williams, A, "Elimination-Addition Mechanism of Acyl Transfer Reactions" 75 : 627-, 1975

      9 Ussing, B. R., "Dynamic effects on the periselectivity, rate, isotope effects, and mechanism of cycloadditions of ketenes with cyclopentadiene" 128 : 7594-, 2006

      10 Bottcher, A, "Darstellung von 1-Oxo-1H-pyrazolo[1,2- a][1,2,4]triazol-4-ium-3-olaten. Eine Ring-Ketten-Tautomerie in der Reihe bicyclischer dipolarer Heterocyclen" 121 : 895-, 1988

      1 Yan, S. J., "Solvent-free, microwave assisted synthesis of polyhalo heterocyclic ketene aminals as novel anti-cancer agents" 20 : 48-, 2010

      2 Sheibani, H, "Mesoionic 1,3- oxazinium olates. Rearrangement to acylketenes and 3- azabicyclo[3.1.1]heptanetriones" 70 : 5859-, 2005

      3 Tidwell, T. T, "Ketenes, 2nd" John Wiley & Sons, Inc 1-, 2006

      4 Taggi, A. E, "Generation of ketenes from acid chlorides using NaH/Crown ether shuttle-deprotonation for use in asymmetric catalysis" 4 : 627-, 2002

      5 Finnerty, J, "Facile 1,3-Shift of chlorine in a Chlorocarbonylketene" 120 : 1701-, 1998

      6 Bornemann, H, "Energy profiles for ketene cyclizations. Interconversion of 1,3-oxazin-6-ones mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products" 70 : 5862-, 2005

      7 Fu, G, "Enantioselective nucleophilic catalysis with "Planar- Chiral" heterocycles" 33 : 412-, 2000

      8 Williams, A, "Elimination-Addition Mechanism of Acyl Transfer Reactions" 75 : 627-, 1975

      9 Ussing, B. R., "Dynamic effects on the periselectivity, rate, isotope effects, and mechanism of cycloadditions of ketenes with cyclopentadiene" 128 : 7594-, 2006

      10 Bottcher, A, "Darstellung von 1-Oxo-1H-pyrazolo[1,2- a][1,2,4]triazol-4-ium-3-olaten. Eine Ring-Ketten-Tautomerie in der Reihe bicyclischer dipolarer Heterocyclen" 121 : 895-, 1988

      11 V. P. Gupta*, "Conformations, Chemical Reactivities and Spectroscopic Characteristics of Some Di-substituted Ketenes: An ab initio Study" 대한화학회 27 (27): 1297-1304, 2006

      12 Tidwell, T. T, "Catalytic asymmetric esterification of ketenes" 44 : 6812-, 2005

      13 Wentrup, C, "Aryliminopropadienone Camidoketenimine amidinoketene-2-aminoquinoline cascades and the ynamine-isocyanate reaction" 64 : 3608-, 1999

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      학술지 이력

      학술지 이력
      연월일 이력구분 이력상세 등재구분
      2027 평가예정 재인증평가 신청대상 (재인증)
      2021-01-01 평가 등재학술지 유지 (재인증) KCI등재
      2018-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2015-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2011-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2009-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2007-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2004-01-01 평가 등재학술지 선정 (등재후보2차) KCI등재
      2003-01-01 평가 등재후보 1차 PASS (등재후보1차) KCI등재후보
      2002-01-01 평가 등재후보학술지 유지 (등재후보1차) KCI등재후보
      1999-07-01 평가 등재후보학술지 선정 (신규평가) KCI등재후보
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      학술지 인용정보

      학술지 인용정보
      기준연도 WOS-KCI 통합IF(2년) KCIF(2년) KCIF(3년)
      2016 0.2 0.2 0.22
      KCIF(4년) KCIF(5년) 중심성지수(3년) 즉시성지수
      0.23 0.18 0.403 0.02
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