PDF herunterladen
Synthesis 2008(21): 3492-3496  
DOI: 10.1055/s-0028-1083178
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regiospecific Bromination of 2-Phenyl-3H-pyrimidin-4-ones

Nilo Zanatta*, Leonardo Fantinel, Liana da S. Fernandes, Ana D. Wouters, Helio G. Bonacorso, Marcos A. P. Martins
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil
Fax: +55(55)2208031; e-Mail: zanatta@base.ufsm.br;
Weitere Informationen

Publikationsverlauf

Received 11 June 2008
Publikationsdatum:
16. Oktober 2008 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Three methods for the regiospecific bromination of 2-phenyl-3H-pyrimidin-4-ones are presented: bromination of the 5-position of the pyrimidine ring, bromination of the 6-benzylic position and simultaneous bromination of both the 5-position of the pyrimidine ring and 6-benzylic position. Reactions were carried out using simple protocols and the brominated pyrimidines were obtained in good yields.

Key words

enones - bromination - bromopyrimidines - pyrimidin-4-ones - 2-phenyl-pyrimidin-4-ones

    References

  • 1 Miyashita O. Matsumura K. Shimatzu H. Hashimoto N. Chem. Pharm. Bull.  1981,  29:  3181 
    CrossrefGoogle Scholar
  • 2 Senda S. Hirota K. Otani O. Yakugaku Zasshi  1974,  94:  571 ; Chem. Abstr. 1974, 81, 91464
    CrossrefPubMedGoogle Scholar
  • 3 Minn K, Braun P, Sachse B, and Wicke H. inventors; Ger. Offen. 4029654,  .  ; Chem. Abstr. 1992, 117, 171466
  • 4a Bucha HC. Loux HM. Harrod JE. Science  1962,  137:  537 
    Google Scholar
  • 4b Loux HM, Luckenbaugh RW, and Soboczenski EJ. inventors; US Patent  3529953.  ; Chem. Abstr. 1963, 147, 316460
  • 5 Wilson DM, Martinborough E, Neubert TD, Termin AP, Gonzales JE, and Zimmermann N. inventors; US Patent  2005049247.  ; Chem. Abstr. 2005, 142, 114092
  • 6a Bradshaw TK. Hutchinson DW. Chem. Soc. Rev.  1977,  6:  43 
    Google Scholar
  • 6b Long RA. Robins RK. Townsend LB. J. Org. Chem.  1967,  32:  2751 
    Google Scholar
  • 7a Wada A. Ohki K. Nagai S. Kanatomo S. J. Heterocycl. Chem.  1991,  28:  509 
    Google Scholar
  • 7b Wada A. Yasuda H. Kanatomo S. Synthesis  1988,  771 
    Google Scholar
  • 8a Robins MJ. Barr PJ. J. Org. Chem.  1983,  48:  1854 
    Google Scholar
  • 8b De Clercq E. Descamps J. Balzarini J. Giziewicz J. Barr PJ. Robins MJ. J. Med. Chem.  1983,  26:  661 
    Google Scholar
  • 9a Yamamoto Y. Seko T. Nemoto H. J. Org. Chem.  1989,  54:  4734 
    Google Scholar
  • 9b Havelková M. Hocek M. Cesnek M. Dvorac D. Synlett  1999,  1145 
    Google Scholar
  • 9c Gong Y. Pauls HW. Synlett  2000,  829 
    Google Scholar
  • 9d Schomaker JM. Delia TJ. J. Org. Chem.  2001,  66:  7125 
    Google Scholar
  • 10a Grible GW. Saulnier MG. Tetrahedron Lett.  1980,  21:  4137 
    Google Scholar
  • 10b Güngör T. Marsais F. Quéguiner G. J. Organomet. Chem.  1981,  215:  139 
    Google Scholar
  • 11 Visser DW. In Synthetic Procedures in Nucleic Acid Chemistry   Vol. 1:  Zorbach WW. Tipson RS. Wiley; New York: 1968.  p.409 
    Google Scholar
  • 12a Fukuhara TK. Visser DW. J. Biol. Chem.  1951,  190:  95 
    Google Scholar
  • 12b Beltz RE. Visser DW. J. Am. Chem. Soc.  1955,  77:  736 
    Google Scholar
  • 13 Duval J. Ebel JP. Bull. Soc. Chim. Biol.  1964,  46:  1059 
    PubMedGoogle Scholar
  • 14 Brammer KW. Biochim. Biophys. Acta  1963,  72:  217 
    CrossrefPubMedGoogle Scholar
  • 15a Sugiyama T. Bull. Chem. Soc. Jpn.  1981,  54:  2847 
    Google Scholar
  • 15b Asakura J. Robins MJ. Tetrahedron Lett.  1988,  29:  2855 
    Google Scholar
  • 15c Asakura J. Robins MJ. J. Org. Chem.  1990,  55:  4928 
    Google Scholar
  • 16 Ondi L. Lefebvre O. Schlosser M. Eur. J. Org. Chem.  2004,  3714 
    CrossrefGoogle Scholar
  • 17a Zanatta N. Flores DC. Madruga CC. Flores AFC. Bonacorso HG. Martins MAP. Tetrahedron Lett.  2006,  47:  573 
    Google Scholar
  • 17b Strekowski L. Wydra L. Janda L. Harden DB. J. Org. Chem.  1991,  56:  5610 
    Google Scholar
  • 17c Kaptein B. Barf G. Kellogg RM. Van Bolhuis F. J. Org. Chem.  1990,  55:  1890 
    Google Scholar
  • 18 Martins MAP. Sinhorin AP. da Rosa A. Flores AFC. Wastowski AD. Pereira CMP. Flores DC. Beck P. Freitag RA. Brondani S. Cunico W. Bonacorso HG. Zanatta N. Synthesis  2002,  2353 
    Artikel in Thieme ConnectGoogle Scholar
  • 19a Botta M. Corelli F. Maga G. Manetti F. Renzulli M. Spadari S. Tetrahedron  2001,  57:  8357 
    Google Scholar
  • 19b Garg R. Gupta SP. Gao H. Babu MS. Debnath AK. Hansch C. Chem. Rev.  1999,  99:  3525 
    Google Scholar
  • 19c Botta M. Occhionero F. Nicoletti R. Mastromarino P. Conti C. Magrini M. Saladino R. Bioorg. Med. Chem.  1999,  7:  1925 
    Google Scholar
  • 20 Zanatta N. Fantinel L. Lourega RG. Bonacorso HG. Martins MAP. Synthesis  2008,  358 
    Artikel in Thieme ConnectGoogle Scholar
  • 21 Tomlin CDS. In The Pesticide Manual   14th ed.:  British Crop Protection Council; UK: 2006.  p.112 
    Google Scholar
  • 22 Ganguly NC. De P. Dutta S. Synthesis  2005,  1103 
    Artikel in Thieme ConnectGoogle Scholar
  • 23a Reigan P. Edwards PN. Gbaj A. Cole C. Barry ST. Page KM. Ashton SE. Luke RWA. Douglas KT. Stratford IJ. Jaffar M. Bryce RA. Freeman S. J. Med. Chem.  2005,  48:  392 
    Google Scholar
  • 23b Yano S. Kazuno H. Suzuki N. Emura T. Wierzba K. Yamashita J.-I. Tada Y. Yamada Y. Fukushima M. Asao T. Bioorg. Med. Chem.  2004,  12:  3431 
    Google Scholar
  • 23c Yano S. Kazuno H. Sato T. Suzuki N. Emura T. Wierzba K. Yamashita J.-I. Tada Y. Yamada Y. Fukushima M. Asao T. Bioorg. Med. Chem.  2004,  12:  3443 
    Google Scholar
  • 23d Klein RS. Lenzi M. Lim TH. Hotchkiss KA. Wilson P. Schwartz EL. Biochem. Pharmacol.  2001,  62:  1257 
    Google Scholar
  • 23e Corelli F. Botta M. Lossani A. Pasquini S. Spadari S. Focher F. Farmaco  2004,  59:  987 
    Google Scholar
  • 24 Colla A. Martins MAP. Clar G. Krimmer S. Fisher P. Synthesis  1991,  483 
    Artikel in Thieme ConnectGoogle Scholar