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새로운 2,4-Diimino-1,3-thiazoles 유도체의 합성과 구조 결정

Synthesis of New 2,4-Diimino-1,3-thiazoles and the Structure Determination

  • 한호규 (한국과학기술연구원 생체과학연구부) ;
  • 임철수 (한국과학기술연구원 생체과학연구부) ;
  • 마혜덕 (경기대학교 화학과)
  • Hoh-Gyu Hahn (Organic Chemistry Lab, Korea Institute of Science and Technology) ;
  • Chul-soo Lim (Organic Chemistry Lab, Korea Institute of Science and Technology) ;
  • Heduck Mah (Department of Chemistry, kyonggi University)
  • 발행 : 2003.02.20

초록

신농약 개발을 목적으로 isosterism 이론을 근거로 하여 선도화합물, 2-imino-1,3-thiazoline의 분자 수정을 통하여 분자내에 1,3-thiazole과 urea기가 포함된 새로운 화합물 2를 디자인하였다. N-Methylthiourea 5와 bromoacetonitrile을 에탄올 용액 중에서 반응시켜 위치 선택적으로 생성된 2,4-diimino-1,3-thiazole 4를 phenylisocyanate 유도체와 반응하여 화합물 2의 tautomer인 7을 얻었고 이것의 구조를 여러 가지 스펙트럼($^1H$ NMR, $^{13}C$ NMR, FT-IR, HRMS)과 X-ray 결정 데이터로부터 확인하였다. 화합물 7의 구조이성질체 8은 열역학적으로 불안정한 중간체 2,4-diimino-1,3-thiazole 6을 통하여 생성되었다.

For the purpose of developing new agrochemical fungicides, compound 2 possessing 1,3-thiazole scaffold as well as urea moiety in the structure was designed through molecular modification of lead compound, 2-imino-1,3-thiazoline based on isosterism. The reaction of N-methylthiouea 5 and bromoacetonitrile in ethanol gave 2,4-diimino-1,3-thiazole 4 regioselectively, which was treated with phenyl isocyanates to give the corresponding 7 which is tautomer of 2. The structural assignment of 7 was confirmed by various spectra($^1H$ NMR, $^{13}C$ NMR, FT-IR, HRMS), and X-ray crystallographic data. Compound 8 which is a structural isomer of 7 was formed through thermodynamically unstable intermediate 2,4-diimino-1,3-thiazole 6.

키워드

참고문헌

  1. Hahn, H.-G.; Nam, K. D.; Kim, B. S.; Cho, K. Y. Agri. Chem. and Biotechnol. 1997, 40, 139.
  2. Patani, G. A.; Lavoie, E. J. Chem. Rev. 1996, 96, 3147. https://doi.org/10.1021/cr950066q
  3. Kavalek, J.; Jirman, J.; Sterba, V. Collect. Czech. Chem. Commun. 1985, 50, 766. https://doi.org/10.1135/cccc19850766
  4. Hahn, H.-G.; Shin, S.-H.; Mah, H. J. Korean Chem. Soc. 2001, 45, 612.

피인용 문헌

  1. Substituent effects of thiazoline derivatives for fungicidal activities against Magnaporthe grisea vol.99, pp.2, 2011, https://doi.org/10.1016/j.pestbp.2010.10.004