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Synthesis 2009(20): 3439-3442  
DOI: 10.1055/s-0029-1216973
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselectivity Change in the Reaction of Naphthalene and 2-Naphthyl Ethers with 1,3,5-Triazines Depending on Reagent Quantities

Alexander V. Aksenov*, Nicolai A. Aksenov, Alexander S. Lyakhovnenko, Inna V. Aksenova
Stavropol State University, Pushkina St. 1, Stavropol 355009, Russian Federation
Fax: +7(8652)357023; e-Mail: alexaks05@rambler.ru;
Further Information

Publication History

Received 8 June 2009
Publication Date:
28 August 2009 (online)

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Abstract

A new method for the synthesis of 4H-benzo[de]isoquinolin-4-ones has been developed, based on the reaction of 2-naphthyl ethers with an equimolar quantity of 1,3,5-triazines in polyphosphoric acid. With a 2.5 molar excess of 1,3,5-triazines in polyphosphoric acid, the products of 1,6-diacylation (diformylation) are formed. Isoquino[6′,5′,4′:10,5,6]anthra[2,1,9-def]isoquinoline is formed upon reaction of a 1.5 molar excess of 1,3,5-triazine with naphthalene in polyphosphoric acid at 130-140 ˚C.

Key words

1,3,5-triazines - polyphosphoric acid - naphthalenes - acylation - 4H-benzo[de]isoquinolin-4-ones - isoquino[6′,5′,4′:10,5,6]anthra[2,1,9-def]isoquinoline

    References

  • For reviews, see:
  • 1a Pozharskii AF. Russ. Chem. Rev. (Engl. Transl.)  2003,  72:  447 
    Google Scholar
  • 1b See also: Olah GA. Ohannesian L. Arvanaghi M. Chem. Rev.  1987,  87:  671 
    Google Scholar
  • 1c Tanaka M. Souma U. J. Chem. Soc., Chem. Commun.  1991,  1551 
    Google Scholar
  • 1d Mutsuo T. Masahiro F. Hisanori A. Yoshie S. J. Org. Chem.  1993,  58:  3213 
    Google Scholar
  • 1e Gorelik AM. Reznichenko AV. Andronova NA. Lyk’yanetz EA. Zh. Org. Khim.  1983,  19:  199 
    Google Scholar
  • 2a Hinkel LE. Ayling EE. Beynon JH. J. Chem. Soc.  1935,  674 
    Google Scholar
  • 2b Grundmann EJ. Kreutzberger AJ. J. Am. Chem. Soc.  1955,  77:  6559 
    Google Scholar
  • 2c Gromov SP. Yashunskii DV. Sagitullin RS. Bundel YuG. Chem. Heterocycl. Compd. (Engl. Transl.)  1992,  9:  1054 
    Google Scholar
  • 2d Bilbao ER. Alvarado M. Masaguer CF. Ravina E. Tetrahedron Lett.  2002,  43:  3551 
    Google Scholar
  • 2e Moehrle H. Pycior M. Arch. Pharm. (Weinheim, Ger.)  1994,  327:  533 
    Google Scholar
  • 2f Schaper W. Synthesis  1985,  861 
    Google Scholar
  • 2g Balogh M. Hermecz I. Naray-Szabo G. Simon K. Meszaros Z. J. Chem. Soc., Perkin Trans. 1  1986,  753 
    Google Scholar
  • 2h Balogh M. Hermecz I. Simon K. Pusztay L. J. Heterocycl. Chem.  1989,  26:  1755 
    Google Scholar
  • 2i Kleinschroth J. Mannhardt K. Hartenstein J. Satzinger G. Synthesis  1986,  859 
    Google Scholar
  • 2j Aksenov AV. Aksenova IV. Chem. Heterocycl. Compd. (Engl. Transl.)  2009,  45:  130 
    Google Scholar
  • 3a Aksenov AV. Borovlev IV. Lyahovnenko AS. Aksenova IV. Chem. Heterocycl. Compd. (Engl. Transl.)  2007,  43:  527 
    Google Scholar
  • 3b Aksenov AV. Borovlev IV. Lyahovnenko AS. Aksenova IV. Russ. J. Org. Chem. (Engl. Transl.)  2007,  43:  1579 
    Google Scholar
  • 3c Aksenov AV. Aksenova IV. Zamorkin AA. Borovlev IV. Russ. J. Org. Chem. (Engl. Transl.)  2008,  44:  151 
    Google Scholar
  • 3d Aksenov AV. Lyahovnenko AS. Aksenova IV. Nadein ON. Tetrahedron Lett.  2008,  49:  1808 
    Google Scholar
  • 3e Aksenov AV. Borovlev IV. Aksenova IV. Kovalev DA. Chem. Heterocycl. Compd. (Engl. Transl.)  2007,  43:  1353 
    Google Scholar
  • 4 Polyphosphoric acid containing 86% P2O5 was used; preparation according to: Uhlig F. Angew. Chem.  1954,  66:  435 
    CrossrefGoogle Scholar
  • 5 Stille JK. Foster RT. J. Org. Chem.  1963,  28:  2703 
    CrossrefGoogle Scholar
  • 6 Schaefer FC. Peters GA. J. Org. Chem.  1961,  26:  2778 
    CrossrefGoogle Scholar
  • 7 Stang PJ. Cao DH. Saito S. Arif AM. J. Am. Chem. Soc.  1995,  117:  6273 
    CrossrefGoogle Scholar