벤조티아졸기를 갖는 새로운 크라운 에테르의 합성

Synthesis of New Crown Ethers Containing Benzothiazole Group

  • 장승현 (대구대학교 자연과학대학 화학과, 기초과학연구소) ;
  • 연애숙 (대구대학교 자연과학대학 화학과, 기초과학연구소) ;
  • 정광보 (한서대학교 공과대학 화학공학과)
  • Chang, Seung-Hyun (Department of Chemistry and Research Institute of Natural Science, Taegu University) ;
  • Yeon, Ae-Sook (Department of Chemistry and Research Institute of Natural Science, Taegu University) ;
  • Chung, Kwang-Bo (Department of Chemistry Engineering Hanseo University)
  • 발행 : 19960200

초록

Crown 고리 근방에 질소, 황원자 를 포함하는 새로운2종의 crown ether를 합성하였다. 4'-Benzothiazolylbenzo-12-crown-4 (1) 4'-Benzothiazolylbenzo-15-crown-5 (2)는 각각 4'-formylbenzo-12-crown-4 (3)및4'-formylbenzo-15-crown-5 (4)와 2-aminothiophenol과의 반응에 의해 합성하였다. (3)과(4)는 3, 4-dihydroxybenzaidehyde와 tri-및 tetraethyleneglycolditosylate와의 반응에 의해 합성하였다. Triethyleneglycolditosylate와 tetraethyleneglycol ditosylate는 NaOH 존재하에서 triethyleneglycol, tetraethyyleneglyco.과 p-toluenesulfonyl chloride의 반응에 의해 합성하였다.

Two new crown ethers containing nitrogen and sulfur atoms adjacent to the crown rings were prepared. 4'-Benzothiazolylbenzo-12-crown-4 (1) or 4'-benzothiazolylbenzo-15-crown-5 (2) were synthesized by reaction of 2-aminothiophenol with 4'-formylbenzo-12-crown-4 (3) or 4'-formylbenzo-15-crown-5 (4) respectively. (3) and (4) were obtained by reaction of 3, 4-dihydroxybenzaldehyde with tri- or tetraethyleneglycol ditosylate. Triethyleneglycol ditosylate or tetraethyleneglycol ditosylate were synthesized by reaction of p-toluenesulfonylchloride with triethyleneglycol or tetraethyleneglycol in the presence of sodium hydroxide.

키워드

참고문헌

  1. J. Am. Chem. Soc. v.89 Pedersen. C.J.
  2. Science v.174 Christensen, J.J.;Hill, J.O.;Izatt, R.M.
  3. Progress in Macrocyclic Chemistry Izatt, R.M.;Christensen, J.J.
  4. Chem. Rev. v.89 Krakwiak, K.E.;Bradshaw, J.S.;Zamecka-Krakowiak, D.J.
  5. Tetrahedron Lett. v.18 Gokel, G.W.;Garcia, B.J.
  6. Synthesis Gokel, G.W.;Dishong, D.M.;Schultz, R.A.;Gatto, V.J.
  7. J. Am. Chem. Soc. v.93 Frensdorff, H.K.
  8. J. Am. Chem. Soc. v.93 Frensdorff, H.K.
  9. J. Am. Chem. Soc. v.97 Lehn, J.M.;Sauvage, J.P.
  10. J. Am. Chem. Soc. v.102 Bradshaw, J.S.;Maas, G.E.;Lamb, J.D.;Izatt, R.M.;Christensen, J.J.
  11. J. Org. Chem. v.47 Montanari, F.;Tundo, P.
  12. J. Am. Chem. Soc. v.96 Timko, J.M.;Helgeson, R.C.;Newcomb, M.;Gokel, G.W.;Cram, D.J.
  13. J. Am. Chem. Soc. v.103 Shinkai, S.;Nakaji, T.;Ogawa, T.;Shigematsu, K.;Manabe, O.
  14. J. Chem. Soc. Chem. Commun. Kimura, E.;Fujioka, H.;Kodama, M.
  15. J. Chem. Soc., Perkin Trans. Ⅱ Shinkai, S.;Minami, T.;Araragi, Y.;Manabe, O.
  16. Chem. Pharm. Bull. v.34 Nakashima, K.;Nakasuji, S.;Akiyama, S.;Kaneda, T.;Misumi, S.
  17. Chem. Lett. Nakamura, H.;Sakka, H.;Takagi, M.;Ueno, K.
  18. Anal. Chem. Acta. v.139 Nakamura, H.;Nishida, H.;Takagi, M.;Ueno, K.
  19. Bunseki Kagaku v.31 Nakamura, H.;Nishida, H.;Takagi, M.;Ueno, K.
  20. J. Org. Chem. v.45 Newkome, G.R.;Kawato, T.;Benton, W.H.
  21. Tetrahedron Lett. v.22 Masuyama, A.;Nakatsuji, Y.;Ikeda, I.;Okahara, M.
  22. Tetrahedron Lett. v.23 Nakatsuji, Y.;Nakamura, T.;Okahara, M.;Dishong, D.M.;Gokel, G.W.
  23. J. Kor. Chem. Soc. v.39 Hong, U.S.;Kwon, H.K.;Cha, G.S.;Nam, H.;Chang, S.H.;Chung, K.B.