Skip to main content
SpringerLink
Log in

Synthesis and autooxidative transformation of 2-(2-aminophenyl)-4-hydroxy-3-phenyl-1-isoquinolone

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-(2-Aminophenyl)-4-hydroxy-3-phenyl-1-isoquinolone was unexpectedly obtained in the reaction of 3-(α-bromobenzyl)-3-bromophthalide with o-phenylenediamine. The isoquinolone in chloroform undergoes autooxidation by air oxygen to give 2-(2-aminophenyl)-3-hydroperoxy-3-phenyl-1,4-dioxo-1,2,3,4-tetrahydroisoquinoline, which is subsequently converted to N-(2-benzamidophenyl)phthalimide. A mechanism is proposed for the rearrangement of the hydroperoxide.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. R. É. Valter and S. P. Valter, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, No. 6, 753

  2. M. V. Bhatt, K. M. Kamath, and M. Ravindranathan, J. Chem. Soc., C, No. 10, 1772 (1971).

    Google Scholar 

  3. R. É. Valter and V. P. Tsiekure, Khim. Geterotsikl. Soedin., No. 4, 502 (1972).

    Google Scholar 

  4. S. M. Abdel Rahman, M. F. Ismail, and Z. M. Ismail, Rev. Roum. Chim., 21, 889 (1976).

    Google Scholar 

  5. R. É. Valter, S. P. Valter, and A. É. Batse, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 2, 367 (1981).

    Google Scholar 

  6. Ya. Ya. Ozol, É. É. Liepin'sh, I. B. Mazheika, B. A. Bigante, and G. Ya. Dubur, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 5, 583 (1978).

    Google Scholar 

  7. J. D. Coyle, J. F. Challiner, E. J. Haws, and G. L. Newport, J. Heterocycl. Chem., 17, 1131 (1980).

    Google Scholar 

  8. A. K. Aren and I. P. Lentsberg, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 677 (1980).

    Google Scholar 

  9. N. N. Khovratovich and N. A. Borisevich, Zh. Prikl. Spektrosk., 8, 443 (1968).

    Google Scholar 

  10. Ya. Ya. Ozol, É. É. Liepin'sh, I. B. Mazheika, B. A. Bigante, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 6, 789 (1978).

    Google Scholar 

  11. J. L. Moniot and M. J. Shamma, J. Org. Chem., 44, 4337 (1979).

    Google Scholar 

  12. L. V. Pavlova and F. Yu. Rachinskii, Usp. Khim., 37, 1369 (1968).

    Google Scholar 

  13. T. Bruce and S. Benkowicz, Mechanisms of Bioorganic Reactions [Russian translation], Mir, Moscow (1970).

    Google Scholar 

  14. D. A. Ramsay, J. Am. Chem. Soc., 74, 72 (1952).

    Google Scholar 

  15. H. Rupe and K. G. Thiess, Chem. Ber., 42, 4287 (1909).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Riga Polytechnic Institute, 226355, Riga

    R. É. Valter, A. É. Batse & S. P. Valter

Authors
  1. R. É. Valter
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. É. Batse
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. P. Valter
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 83–87, January, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Valter, R.É., Batse, A.É. & Valter, S.P. Synthesis and autooxidative transformation of 2-(2-aminophenyl)-4-hydroxy-3-phenyl-1-isoquinolone. Chem Heterocycl Compd 18, 70–74 (1982). https://doi.org/10.1007/BF00513293

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00513293

Keywords

Search

Navigation