Chemistry of Heterocyclic Compounds

, Volume 46, Issue 5, pp 620–622 | Cite as

Syntheses of 3-substituted 3,4-dihydroisochromen-1-ones

  • S. Mohana Roopan
  • P. Deepika
  • U. M. V. Basavanag
  • F. Nawaz Khan
The isochromen-1-one skeleton is found in a variety of natural products [ 1]. Isocoumarins and their derivatives, such as dihydroisocoumarins, are secondary metabolites of a wide variety of microbial, plant, and insect sources and are used in the synthesis of other medicinal compounds [ 2, 3, 4]. Most methods available for the construction of 3-substituted 3,4-dihydroisochromen-1-one nucleus suffer from one or more drawbacks, such as the multistep procedure [ 5] and use of expensive and hazardous reagents and solvents. Many studies on isocoumarin synthesis, including cyclization of keto acids and electrophilic cyclization of alkynylbenzoic acid derivatives, have been reported [ 6, 7]. Finding an efficient method for the synthesis of 3,4-dihydroisochromen-1-one is still a challenge.


isochromen-1-one montmorillonite K-10 


  1. 1.
    R. A. Hill, Naturally Occurring Isocoumarins, in: Progress in the Chemistry of Natural Compounds, Vol. 49, 1986, p. 1.Google Scholar
  2. 2.
    H. Szmant, Organic Building Blocks of the Chemical Industry, Wiley, New York, 1989.Google Scholar
  3. 3.
    G. Qadeer, N. H. Rama, and S. J. H. Shah, ARKIVOC, xiv, 12 (2007).Google Scholar
  4. 4.
    P. Manivel, S. Mohana Roopan, and F. Nawaz Khan, J. Chil. Chem. Soc., 53, 1126 (2008).CrossRefGoogle Scholar
  5. 5.
    V. S. Matiychuk, V. V. Turytsya, and N. D. Obushak, Khim. Geterotsikl. Soed., 1875 (2007). [Chem. Heterocycl. Comp., 43, 1589 (2007)].Google Scholar
  6. 6.
    T. Yao and C.R. Larock, J. Org. Chem., 68, 5936 (1986).CrossRefGoogle Scholar
  7. 7.
    T. Suzuki, T. Yamada, K. Watanabe, and T. Katoh, Bioorg. Med. Chem. Lett., 15, 2583 (2005).CrossRefGoogle Scholar
  8. 8.
    Venkatesha R. Hathwar, P. Manivel, F. Nawaz Khan, and T. N. Guru Row, Acta Crystallogr., E63, o3707 (2007).Google Scholar
  9. 9.
    Venkatesha R. Hathwar, P. Manivel, F. Nawaz Khan, and T. N. Guru Row, Acta Crystallogr., E63, o3708 (2007).Google Scholar
  10. 10.
    S. Mohana Roopan, and F. Nawaz Khan, Indian J. Heterocycl. Chem., 18, 183 (2008).Google Scholar
  11. 11.
    S. Mohana Roopan, T. Maiyalagan, and F. Nawaz Khan, Can. J. Chem. 86, 1019 (2008).CrossRefGoogle Scholar
  12. 12.
    Venkatesha R. Hathwar, P. Manivel, F. Nawaz Khan, and T. N. Guru Row, Cryst. Eng. Comm., 11, 284 (2009).Google Scholar
  13. 13.
    S. Syed Tajudeen and F. Nawaz Khan, Synth. Comm., 37, 3649 (2007).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • S. Mohana Roopan
    • 1
  • P. Deepika
    • 1
  • U. M. V. Basavanag
    • 1
  • F. Nawaz Khan
    • 1
  1. 1.Organic & Medicinal Chemistry Research Laboratory, School of Advanced SciencesVIT - UniversityVelloreIndia

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