수용액과 β-Cyclodextrin 하에서 Arylidenethiosemicarbazone들로부터 1,3-Thiazole 유도체들의 효율적 합성

Efficient Synthesis of 1,3-Thiazole Derivatives from Arylidenethiosemicarbazones in the Presence of β-Cyclodextrin with Water

  • 박경진 (군산대학교 화학과) ;
  • 배선건 (군산대학교 화학과)
  • Park, Kyung-Jin (Department of Chemistry, Kunsan National University) ;
  • Bae, Sun Kun (Department of Chemistry, Kunsan National University)
  • 투고 : 2007.04.23
  • 심사 : 2007.06.20
  • 발행 : 2007.08.10

초록

수용액 상에서 ${\beta}$-cyclodextrin에 2,4'-dibromoacetophenone (8)을 반응시켜 착물을 형성한 후 arylidenethiosemicarbazone 7a-f를 가하여 2-arylidenehydrazinyl-4-arylthiazole 유도체들 9a-f를 70~88% 수율로 합성하였다. 합성한 새로운 화합물들 9a-f의 구조를 IR과 $^1H-NMR$ 스펙트럼 자료로 확인하였다. 이와 같은 실험결과 ${\beta}$-cyclodextrin의 역할은 반응물 7 및 8의 활성화로 반응을 촉진시켜 반응시간이 단축되는 것으로 나타났다.

키워드

1,3-thiazole;complex;arylidenethiosemicarbazone;2,4'-dibromoacetophenone;${\beta}$-cyclodextrin

참고문헌

  1. J. Das, C, Liu, R. V. Moquin, S. H. Spergel, K. W. Mclntyre, and D. J. Shuster, Bioorg. Med. Chem. Lett, 16, 3706 (2006) https://doi.org/10.1016/j.bmcl.2006.04.060
  2. S. K. Bae and H. T. Kim, J. Basic and Life Res. Sci., 3, 14 (2003)
  3. A. Tsuruoka, Y. Kaku, H. Kakinuma, I. Tsukada, and T. Naito, Chem. Pharm. Bull., 45, 1169 (1997)
  4. L. Novak, J. Rohaly, and C. Szantay, OPP BRIEFS, 31, 693 (1999)
  5. M. C. Bagley and C. Glover, Tetrahedron, 62, 66 (2006) https://doi.org/10.1016/j.tet.2005.09.134
  6. T. Aoyama, S. Murata, I. Arai, Y. Sukuki, and M. Kodomori, Tetrahedron, 62, 1 (2006) https://doi.org/10.1016/S0040-4020(05)02083-1
  7. R. Pereira, C. Gaudon, B. Lelesias, P. Germain, H. Gronemeyer, and R. De Lera, Bioorg. Med. Chem. Lett. 16, 49 (2006) https://doi.org/10.1016/j.bmcl.2005.09.060
  8. S. C. Sinha, S. Dutta, and J. Sun, Tetrahedron Lett, 41, 8243 (2002) https://doi.org/10.1016/S0040-4039(00)01469-6
  9. T. Barf, R. Emond, G. Kurz, A. Nygren, R. Olsson, and P. Alberts, J. Med. Chem., 45, 3814 (2002)
  10. T. Yamane, H. Mitsudera, and T. Shundoh, Tetrahedron Lett, 45, 69 (2004) https://doi.org/10.1016/j.tetlet.2003.10.113
  11. M. Narender, M. S. Reddy, R. Sridhra, Y. V. D. Nageswar, and K. R. Rao, Tetrahdron Lett. 46, 5953 (2005) https://doi.org/10.1016/j.tetlet.2005.06.130
  12. J. J. Harnett, V. Roubert, C. Dolo, C. Charnet, B. Spinnewyn, S. Cornet, A. Rlooand, J. G. Marin, D. Bigg, and P. E. Charbier, Bioorg. & Med. Chem. Lett. 14, 157 (2004) https://doi.org/10.1016/j.bmcl.2003.09.077
  13. K. Okumura, H. Saito, C. G. Shin, K. Umemura, and J. Yoshimura, Bull. Chem. Soc. Jpn., 71, 1863 (1998)
  14. R. Zao, S. Gove, J. E. Sundeen, and B. C. Chen, Tetrahedron Lett, 42, 2101 (2001) https://doi.org/10.1016/S0040-4039(01)00161-7