Skip to main content
Log in

Efficient synthesis of some 3-arylisoquinolin-1(2H)-ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A number of 3-arylisoquinolin-1(2H)-ones were efficiently prepared from the corresponding 3-aryl-isocoumarins by refluxing with methanamide.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. C.-Y. Chen, F.-R. Chang, C.-M. Teng, and Y.-C. Wu, J. Chin. Chem. Soc., 46, 77 (1999).

    CAS  Google Scholar 

  2. G. R. Pettit, Y. Meng, D. L. Herald, N. K. A. Graham, R. K. Pettit, and D. L. Doubek, J. Nat. Prod., 66, 1065(2003).

    Article  CAS  Google Scholar 

  3. D. Gonzalez, T. Martinot, and T. Hudlicky, Tetrahedron Lett., 40, 3077 (1999).

    Article  CAS  Google Scholar 

  4. R. C. Thompson and J. Kallmerten, J. Org. Chem., 55, 6076 (1990).

    Article  CAS  Google Scholar 

  5. M. Shamma and J. L. Moniot, Isoquinoline Alkaloids Research, 1972–1977, Plenum Press, New York, London, 1978, p. 57.

    Google Scholar 

  6. A. A. Semenov, The Chemistry of Natural Compounds [in Russian], Nauka/Siberian Printing Company of the Russian Academy of Sciences, Novosibirsk, 2000.

    Google Scholar 

  7. M. Shamma and J. E. Foy, Tetrahedron Lett., 2249 (1975).

  8. T. Okomoto, Y. Torii, and Y. Isogai, Chem. Pharm. Bull., 16, 1860 (1968).

    Google Scholar 

  9. M. J. Fisher, B. P. Gunn, S. Um, and J. A. Jakubowski, Tetrahedron Lett., 38, 5747 (1997).

    Article  CAS  Google Scholar 

  10. T. Matsui, T. Sugiura, H. Nakai, S. Iguchi, S. Shigeoka, H. Takada, Y. Odagaki, Y. Nagao, Y. Ushio, K. Ohmoto, H. Iwamura, S. Yamazaki, Y. Arai, and M. Kawamura, J. Med. Chem., 35, 3307 (1992).

    Article  CAS  Google Scholar 

  11. S. W. Li, M. G. Nair, D. M. Edwards, R. L. Kisliuk, Y. Gaumont, I. K. Dev, D. S. Duch, J. Humphreys, G. K. Smith, and R. Ferone, J. Med. Chem., 34, 2746 (1991).

    Article  CAS  Google Scholar 

  12. Q. Chao, L. Deng, H. Shih, L. M. Leoni, D. Genini, D. A. Carson, and H. B. Cottam, J. Med. Chem., 42, 3860 (1999).

    Article  CAS  Google Scholar 

  13. T. S. Sulkovski and M. A. Wille, US Pat. 3452027; Chem. Abstr., 71, 112830 (1969).

    Google Scholar 

  14. K. Kubo, N. Ito, I. Souzu, Y. Isomura, and H. Homma, Ger. Offen 2828528; Chem. Abstr., 90, 168468 (1979).

    Google Scholar 

  15. O. Senda, O. Ohtani, E. Katho, H. Miyake, and K. Fujiwara, Ger. Offen 3031574; Chem. Abstr., 95, 132692 (1981).

    Google Scholar 

  16. M. Hasegava, K. Shirai, K. Matsumoto, Y. Suzuki, and I. Takahasi, US Pat. 5441962; Chem. Abstr., 121, 912 (1994).

    Google Scholar 

  17. S. Gabriel and J. Colman, Ber., 33, 980 (1900).

    Google Scholar 

  18. M. C. Delcey, C. Huel, and E. Bisagni, Heterocycles, 41, 1721 (1995).

    CAS  Google Scholar 

  19. J. E. Semple, R. M. Rydzewski, and G. Gardner, J. Org. Chem., 61, 7967 (1996).

    Article  CAS  Google Scholar 

  20. Y. Cheng, H.-B. Tsai, and M.-S. Lin, J. Heterocycl. Chem., 32, 73 (1995).

    CAS  Google Scholar 

  21. A. Sugimoto, H. Shinba-Tanaka, and M. Ishikava, Synthesis, 431 (1995).

  22. J. Dusemund and T. Hardt, Arch. Pharm., 321, 41 (1988).

    Article  CAS  Google Scholar 

  23. S. Yamaguchi, Y. Uchiuzoh, and K. Sanada, J. Heterocycl. Chem., 32, 419 (1995).

    Article  CAS  Google Scholar 

  24. S. Ohta and S. Kimoto, Tetrahedron Lett., 2279 (1975).

  25. M. Khaldi, F. Chrétien, and Y. Chapleur, Tetrahedron Lett., 36, 3003 (1995).

    Article  CAS  Google Scholar 

  26. G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 117, 7289 (1995).

    Article  CAS  Google Scholar 

  27. T. Minami, A. Nishimoto, and M. Hanaoka, Tetrahedron Lett., 36, 9505 (1995).

    Article  CAS  Google Scholar 

  28. R. Connors, E. Tran, and T. Durst, Can. J. Chem., 74, 221 (1996).

    Article  CAS  Google Scholar 

  29. J. H. Van Duzer and D. M. Rol, Eur. Pat. 526402; Chem. Abstr., 119, 8694 (1993).

    Google Scholar 

  30. M.-S. Chern and W.-R. Li, Tetrahedron Lett., 45, 8323 (2004).

    Article  CAS  Google Scholar 

  31. M. W. Khan and A. F. G. M. Reza, Tetrahedron, 61, 11204 (2005).

    Article  CAS  Google Scholar 

  32. E. P. Souza and P. S. Fernes, Indian J. Chem., 29B, 961 (1990).

    Google Scholar 

  33. S. Ferrer, D. P. Naughton, H. Parveen, and M. D. Threadgill, J. Chem. Soc., Perkin Trans. 1, 335 (2002).

  34. T. Sakamoto, M. Annaka, Y. Kondo, and H. Yamanaka, Chem. Pharm. Bull., 34, 2754 (1986).

    CAS  Google Scholar 

  35. A. S. Dmitriev, V. T. Abaev, and A. V. Butin, Chem. Heterocycl. Comp., 41, 1197 (2005). [XTC, 1402 (2005)].

    Article  CAS  Google Scholar 

  36. E. Napolitano, Org. Prep. Proced. Int., 29, 631 (1997).

    CAS  Google Scholar 

  37. A. Saeed, Helv. Chim. Acta, 86, 377 (2003).

    Article  CAS  Google Scholar 

  38. A. Saeed, J. Heterocycl. Chem., 40, 337 (2003).

    CAS  Google Scholar 

  39. A. Saeed, Nat. Prod. Res., 18, 373 (2004).

    Article  CAS  Google Scholar 

  40. A. Saeed and S. Ehsan, J. Braz. Chem. Soc., 16, 739 (2005).

    Article  CAS  Google Scholar 

  41. A. Saeed, J. Asian Nat. Prod. Res., 8, 417 (2006).

    Article  CAS  Google Scholar 

  42. A. Saeed, Synth. Commun., 37, 1485 (2007).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Aamer Saeed.

Additional information

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1203–1208, August, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Saeed, A., Ashraf, Z. Efficient synthesis of some 3-arylisoquinolin-1(2H)-ones. Chem Heterocycl Comp 44, 967–972 (2008). https://doi.org/10.1007/s10593-008-0140-3

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-008-0140-3

Keywords

Navigation