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


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.


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


  1. 한호규, 신선호, 마혜덕 (2001b) Synthesis of 2-Benzylimino-1,3-thiazoline 유도체의 합성 및 구조 규명. 대한화학회지 45(6):612-615
  2. Bramley, S. E., G. C. Gogerdhan and V. D. Dhanesh (1987) The Hantzsch Thiazole Synthesis under Acidic Conditions: Change of Regioselectivity. J. Chem. Soc. Perkin Trans. 1. 639-643
  3. 한호규, 남기달, 신선호, 마혜덕 (2001a) 2-Phenylimino-1,3-thizoline 염산염 유도체의 합성 한국농약과학회지 5(2):13-17
  4. Tanaka, T., Y. Nakamoto, K. Maekawa, M. Watanabe, C. Nishihara and C. Iwata (1996) Reaction of 3-aralkylsulfony1-2-(N-cyanoimino)thiazolidines with oxygen nucleophiles. Heterocycles 42(1):265-272
  5. Hurd, C. D and J. L. Abernethy (1940) The Chlorination and the Structure of Acetylketene. J. Am. Chem. Soc. 62:1147~1148
  6. Pavia, D. L., G. M. Lampman and G. S. Kriz (1996) Introduction to Spectroscopy, pp.188-190, Saunders College Publishing, U.S.A