Chemistry of Heterocyclic Compounds

, Volume 48, Issue 1, pp 2–6 | Cite as

Linear encoding of functional groups in the synthesis of heterocyclic compounds: cycloaddition of enyne and alkyne units

  • V. P. Ananikov

A family of novel [4 + 2] cycloaddition reactions is discussed for the efficient preparation of poly-substituted heterocyclic compounds in a single step starting with linear precursors. The high selectivity of the intramolecular transformation and the predefined position of the substituents in the product were governed by linear encoding in the structure of the starting reagents. The designed reactions utilized the green chemistry potential of the cycloaddition approach and provided a convenient synthetic route to cyclopentapyridines, indoles, isoindoles, indolizines, isophosphindoles, benzofurans, benzothiophenes, and benzoselenophenes (and corresponding dihydro derivatives).


alkyne cyclic allene enyne cycloaddition cycloaromatization selectivity 


  1. 1.
    P. T. Anastas and M. M. Kirchhoff, Acc. Chem. Res., 35, 686 (2002).CrossRefGoogle Scholar
  2. 2.
    P. Wessig and G. Müller, Chem. Rev., 108, 2051 (2008).CrossRefGoogle Scholar
  3. 3.
    A. Ajaz, A. Z. Bradley, R. C. Burrell, W. H. H. Li, K. J. Daoust, L. B. Bovee, K. J. DiRico, and R. P. Johnson, J. Org. Chem., 76, 9320 (2011).CrossRefGoogle Scholar
  4. 4.
    R. C. Burrell, K. J. Daoust, A. Z. Bradley, K. J. DiRico, and R. P. Johnson, J. Am. Chem. Soc., 118, 4218 (1996).CrossRefGoogle Scholar
  5. 5.
    V. Gevorgyan and Y. Yamamoto, J. Organomet. Chem., 576, 232 (1999).CrossRefGoogle Scholar
  6. 6.
    M. Rubin, A. W. Sromek, and V. Gevorgyan, Synlett, 2265 (2003).Google Scholar
  7. 7.
    M. Rubina, M. Conley, and V. Gevorgyan, J. Am. Chem. Soc., 128, 5818 (2006).CrossRefGoogle Scholar
  8. 8.
    R. L. Danheiser, A. E. Gould, R. F. de la Pradilla, and A. L. Helgason, J. Org. Chem., 59, 5514 (1994).CrossRefGoogle Scholar
  9. 9.
    M. S. B. Wills and R. L. Danheiser, J. Am. Chem. Soc., 120, 9378 (1998).CrossRefGoogle Scholar
  10. 10.
    J. R. Dunetz and R. L. Danheiser, J. Am. Chem. Soc., 127, 5776 (2005).CrossRefGoogle Scholar
  11. 11.
    V. P. Ananikov, J. Phys. Org. Chem., 14, 109 (2001).CrossRefGoogle Scholar
  12. 12.
    V. P. Ananikov, J. Phys. Org. Chem., 16, 253 (2003).CrossRefGoogle Scholar
  13. 13.
    I. V. Alabugin, M. Manoharan, B. Breiner, and F. D. Lewis, J. Am. Chem. Soc., 125, 9329 (2003).CrossRefGoogle Scholar
  14. 14.
    V. P. Ananikov and E. G. Gordeev, Chem. Sci., 2, 2332 (2011).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  1. 1.M. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia

Personalised recommendations