• Title/Summary/Keyword: dimethyl acetylenedicarboxylate

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Synthesis of Protoberberine Related Compounds and Their Antifungal Activities (프로토베르베린 관련 화합물합성 및 항균작용)

  • Kim, Sin-Kyu;Kim, Dong-Hyun;Chung, Kyung-Hee;Hwang, Soon-Ho;Kim, Jae-Hyun
    • YAKHAK HOEJI
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    • v.38 no.1
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    • pp.91-96
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    • 1994
  • Irradiation of the berberinephenolbetaine [1] effected valence tautamerization to five 8,14-cycloberbine[21, which was converted to the spirobenzylisoquinolines by regioselective C-N bond cleavage A variety of ring systems such as compounds [4], [5] and [6] were introduced by the structural modification of berberinephenolbetaine.

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A Selective Synthesis of Isoxazolo[2,3-${\alpha}$]quinoxalines and Pyrrolo[1,2-${\alpha}$]quinoxalines by 1,3-Dipolar Cycloaddition Reaction (1,3-쌍극성 고리화 첨가반응에 의한 Isoxazolo[2,3-${\alpha}$]quinoxaline류와 Pyrrolo[1,2-${\alpha}$]quinoxaline류의 선택적인 합성)

  • Kim Ho Sik;Nam Soon Hwa;Kurasawa Yoshihisa
    • Journal of the Korean Chemical Society
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    • v.34 no.5
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    • pp.469-475
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    • 1990
  • The reaction of 2,6-dichloroquinoxaline (13) with m-chloroperbenzoic acid gave 2,6-dichloroquinoxaline 4-oxide (14), whose reaction with pyrrolidine or indoline provided 2-substituted 6-chloroquinoxaline 4-oxides (15). The isoxazolo[2,3-a]quinoxalines (16) and pyrrolo[1,2-a]quinoxalines (17) were selectively synthesized from the 2-substituted 6-chloroquinoxaline 4-oxides (15) and dimethyl acetylenedicarboxylate. Moreover, the pyrrolo[1,2-a]quinoxalines (17) were found to be produced by the ring transformation of the isoxazolo[2,3-a]quinoxalines (16).

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Synthesis of Pyrazolylquinoxalines and Pyrazolylpyrrolo[1,2-a]-quinoxalines (Pyrazolylquinoxaline류 및 Pyrazolylpyrrolo[1,2-a]-quinoxaline류의 합성)

  • Kim, Ho Sik;Lee, Seong Uk;Jeong, Won Young;Han, Sung Wook;Kim, Dong Il;Yoshihisa Kurasawa
    • Journal of the Korean Chemical Society
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    • v.45 no.4
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    • pp.318-324
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    • 2001
  • The reaction of 6-chloro-2-hydrazinoquinoxaline(4) or 6-chloro-2-hydrazinoquinoxaline 4-oxide(7) with alkyl (ethoxymethylene)cyanoacetates gave pyrazolylquinoxalines(5, 8). The reaction of compounds 8 with dimethyl acetylenedicarboxylate resulted in the 1,3-dipolar cycloaddition reaction and then ring transformation to afford pyrazolylpyrrolo[1,2-a]quinoxalines(9).

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Synthesis of Tetrazolo[1,5-a]quinoxalines with Antimicrobial Activity (항균성을 가진 Tetrazolo[1,5-a]quinoxaline류의 합성)

  • Kim, Ho Sik;Kim, Dong Eun;Yoshihisa Kurasawa
    • Journal of the Korean Chemical Society
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    • v.45 no.4
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    • pp.325-333
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    • 2001
  • The 4-substituted tetrazolo[1,5-a]quinoxalines were synthesized from 4-chlorotetrazolo-[1,5-a]quinoxaline(8) or 4-hydrazinotetrazolo[1,5-a]quinoxaline(9). Refluxing of the tetrazolo[1,5-a]quinoxaline(12) in N,N-dimethylformamide gave the 1,2,4-triazolo[3,4-c]tetrazolo[1,5-a]quinoxaline(13), which was also obtained by the reaction of compound 9 with ethyl chloroformate in N,N-dimethylformamide. The reaction of compound 9 with isothiocyanates in ethanol provided the tetrazolo[1,5-a]quinoxalines(14), whose reaction with dimethyl acetylenedicarboxylate afforded the tetrazolo[1,5-a]quinoxalines(15). The tetrazolo [1,5-a]quinoxalines(18) were obtained by the reaction of compound 9 with alkyl (ethoxymethylene)cyanoacetates. Some of the compounds showed antibacterial, antifungal or algicidal activities against some strains.

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