Synthesis of 2-Cyanoimino-1,3-thiazoline

2-Cyanoimino-1,3-thiazoline 유도체의 합성

  • Hahn, Hoh-Gyu (Organic Chemistry Lab, Korea Institute of Science and Technology) ;
  • Nam, Kee-Dal (Organic Chemistry Lab, Korea Institute of Science and Technology) ;
  • Park, Ik-Kyu (Department of Chemistry, Kyunggi University) ;
  • Mah, He-Duck (Department of Chemistry, Kyunggi University)
  • 한호규 (한국과학기술연구원 생체과학연구부) ;
  • 남기달 (한국과학기술연구원 생체과학연구부) ;
  • 박익규 (경기대학교 화학과) ;
  • 마혜덕 (경기대학교 화학과)
  • Published : 2003.06.30

Abstract

2-Imino-1,3-thiazolines 1 show selective antifungal activity against pyricularia oryzae by new mode of action. A synthesis of novel 2-cyano-l,3-thiazolines 2 in which cyano moiety is substituted in imino group at C-2 of 1 is described. The lone pair electrons of sulfur and nitrogen as well as strong electron withdrawing cyano substituent in 1,3-thiazoline scaffold would effect the biological activity of 2-imino-1,3-thiazoline series. Regiospecific nucleophilic attack of thiourea 4 for $\gamma$-chloro-$\beta$-ketoacetoacetanilide 3 followed by acid catalyzed dehydration gave 2.

Keywords

agrochemical fungicide;pyricularia oryzae;1,3-thiazoline;stereospecific nucleophilic attack

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