Selective mono- and bis-condensations of isophthalaldehyde derivative with 6-(o-aminoanilino)cyclodextrins

(Note: The full text of this document is currently only available in the PDF Version )

De-Qi Yuan, Kahee Fujita, Hidefumi Mizushima and Masatoshi Yamaguchi


Abstract

Selective mono- and bis-condensations of an isophthalaldehyde derivative with a stoichiometric amount of 6-(o-aminoanilino)-α- (or β-) cyclodextrin to afford 2-(formylphenyl)benzimidazole-pendant α- (or β-) cyclodextrin and bisbenzimidazole-bridged homo- or hetero-dimers of cyclodextrins are described.


References

  1. G. Wenz, Angew. Chem., Int. Ed. Engl., 1994, 33, 803 CrossRef and references cited therein.
  2. K. Fujita, T. Tahara, H. Yamamura, T. Imoto, T. Koga, T. Fujioka and K. Mihashi, J. Org. Chem., 1990, 55, 877 CrossRef CAS; D. Rong and V. T. D'Souza, Tetrahedron Lett., 1990, 31, 4275 CrossRef CAS; T. Tahara, K. Fujita and T. Koga, Bull. Chem. Soc. Jpn., 1990, 63, 1409 CAS; I. Tabushi, K. Shimokawa and K. Fujita, Tetrahedron Lett., 1977, 18, 1527 CrossRef; L. D. Melton and K. N. Slessor, Carbohydr. Res., 1971, 18, 29 CrossRef CAS.
  3. F. Venema, C. M. Baselier, M. C. Feiters and R. J. M. Molte, Tetrahedron Lett., 1994, 46, 8661 CrossRef CAS.
  4. V. Cucinotta, F. D'Alessandro, G. Impellizzeri, G. Pappalado, E. Rezzarelli and G. Vecchio, J. Chem. Soc., Chem. Commun., 1991, 293 RSC; Y. Du, A. Nakamura and F. Toda, Bull. Chem. Soc. Jpn., 1990, 63, 3351 CAS; Y. Kuroda, Y. Sasaki, Y. Shiroiwa and I. Tabushi, J. Am. Chem. Soc., 1988, 110, 4049 CrossRef CAS; I. Tabushi, Y. Kuroda, M. Yamada, H. Higashimura and R. Breslow, J. Am. Chem. Soc., 1985, 107, 5545 CrossRef CAS.
  5. D.-Q. Yuan, K. Koga, Y. Yamaguchi and K. Fujita, Chem. Commun., 1996, 1943 RSC.
  6. R. Breslow, Acc. Chem. Res., 1995, 28, 146 CrossRef CAS; R. Breslow, S. Halfon and B. Zhang, Tetrahedron, 1995, 51, 377 CrossRef CAS; K. Fujita, S. Ejima and T. Imoto, J. Chem. Soc., Chem. Commun., 1984, 1277 RSC.
  7. Y. Okabe, H. Yamamura, K. Obe, K. Ohta, M. Kawai and K. Fujita, J. Chem. Soc., Chem. Commun., 1995, 581 RSC; F. Venema, Y. Wang, A. Ueno and F. Toda, Chem. Lett., 1994, 167.
  8. Similar phenomena are recently reported; C. J. Easton, S. J. van Eyk, S. F. Lincoln, B. L. May, J. Papageorgiou and M. L. Williams, Aust. J. Chem., 1997, 50, 9 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.