Advertisement

Catalysis Letters

, Volume 98, Issue 2–3, pp 117–121 | Cite as

Bis(cyclopentadienyl)zirconium Dichloride for Alkylation of Heteroaromatics and Synthesis of Bis(indolyl)methanes

  • M. Lakshmi Kantam
  • Khathija Aziz
  • Pravin R. Likhar
Article

Abstract

Bis(cyclopentadienyl)zirconium dichloride catalyzed alkylation of heteroaromatics with epoxides results in the formation of 3-alkylated heteroaromatics in high yields. Cp2 ZrCl2 is also found to be an efficient catalyst for the electrophilic substitution reaction of indoles with aldehydes and ketones to afford the corresponding bis(indolyl)methanes in high yields with complete regioselectivity.

bis(cyclopentadienyl) zirconium dichloride epoxide indoles bis-(indolyl)methane 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    (a)U. Pindur and R. Adam, J. Heterocyclic Chem. 25 (1988) 1; (b)J. P. Dirlam, D. A. Clark, S. J. Hecker, J. Org. Chem. 51 (1986) 4920;(c)R. J. Sundberg, The Chemistry of Indoles (Academic Press, New York, 1970).Google Scholar
  2. [2]
    (a)M. Tani, P. Aoki, S. Ito, S. Matsumoto, M. Hibeshima, K. Fukushima, R. Nozauua, T. Maeda, Tashiro, Y. Yokoyama and Y. Murakami, Chem. Pharm. Bull. 38 (1990) 3261;(b)R. Settambolo, R. Lazzaroni, P. Messeri, M. Mazzetti, P. Salvadori, J. Org. Chem. 58 (1993) 7899.Google Scholar
  3. [3]
    (a)W. Kaminsky and A. Laban, Appl. Catal. A 222 (2001) 47;(b) W. Kaminsky, Catal. Today. 62 (2000) 23; (c)W. Kaminsky, Macromol. Chem. Phys. 197 (1996) 3907.Google Scholar
  4. [4]
    A. Maureen Rouhi, Chem. Eng. News 82 (2004) 36.Google Scholar
  5. [5]
    H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, Tetrahedron Lett. 37 (1996) 3727.Google Scholar
  6. [6]
    (a)H. Kotsuki, K. Hayashida, T. Shimanouchi and H. Nishizawa, J. Org. Chem. 61 (1996) 984;(b)H. Kotsuki, M. Nishiuchi, S. Kobayashi, H. Nishizawa, J. Org. Chem. 55 (1990) 2969.Google Scholar
  7. [7]
    J. S. Yadav, B. V. S. Reddy, S. Abraham and G. Sabita, Synlett (2002) 1550.Google Scholar
  8. [8]
    S. A. Morris and R. J. Anderson, Tetrahedron 46 (1990) 715.Google Scholar
  9. [9]
    (a)P. Ehrlish, Med. Woche (1901) 151;(b)H. Uk, Pharm. Weekbl. 66 (1929) 473;(c)L. Morgan, R. J. Schunior, J. Org. Chem. 1962, 27, 3696;(d)D. J. Dolpin, J. Heterocycl. Chem. 7 (1979) 275.Google Scholar
  10. [10]
    (a)B. Gregorovich, K. Liang, D. Clugston and S. MacDonald, Can. J. Chem. 46 (1968) 3291; (b)M. Roomi, S. MacDonald, Can. J. Chem. 48 (1970) 139.Google Scholar
  11. [11]
    D. Chen, L. Yu and P. G. Wang, Tetrahedron Lett. 37 (1996) 4467.Google Scholar
  12. [12]
    (a)A. Chatterji, S. Manna, S. Banerji, C. Pascard, T. Prange and J. Shoolery, J. Chem. Soc. Perkin Trans. 1 (1980) 533;(b)W. Noland, M. Venkiteswaran, C. Richards, J. Org. Chem. 26 (1961) 4241.Google Scholar
  13. [13]
    S. Kobayashi, M. Araki and M. Yasuda, Tetrahedron Lett. 36 (1995) 5773.Google Scholar
  14. [14]
    M. L. Kantam, K. Aziz, K. Jeyalakshmi and P. R. Likhar, Catal. Lett. 89 (2003) 95.Google Scholar
  15. [15]
    R. B. King and F. G. A. Stone, Inorg. Syn. 7 (1963) 101.Google Scholar

Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • M. Lakshmi Kantam
    • 1
  • Khathija Aziz
    • 1
  • Pravin R. Likhar
    • 1
  1. 1.Indian Institute of Chemical TechnologyIndia

Personalised recommendations