PDF herunterladen
Synthesis 2010(15): 2583-2587  
DOI: 10.1055/s-0029-1218841
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Expedient Microwave-Assisted Synthesis of 5-Benzoylamino-2-(aralkylsulfanyl)pyrimidin-4(3H)-ones

Finn K. Hansen, Detlef Geffken*
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany
Fax: +49(40)428386573; e-Mail: geffken@chemie.uni-hamburg.de;
Weitere Informationen

Publikationsverlauf

Received 18 February 2010
Publikationsdatum:
29. Juni 2010 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

A rapid and efficient microwave-assisted synthesis of novel 5-benzoylamino-2-(aralkylsulfanyl)pyrimidin-4(3H)-ones by rearrangement of 4-(1-ethoxyalkylidene)-2-phenyloxazol-5(4H)-ones in the presence of S-aralkyl-substituted isothiouronium halides and triethylamine is reported

Key words

microwave-assisted synthesis - azlactones - ring expansion - rearrangement - 2-(aralkylsulfanyl)pyrimidin-4(3H)-ones

    References

  • 1 Kwan P. Brodie MJ. Epilepsia  2004,  45:  1141 
    CrossrefPubMedSuche in Google Scholar
  • 2a Botta M. Artico M. Massa S. Gambacorta A. Marongiu ME. Pani A. La Colla P. Eur. J. Med. Chem.  1992,  27:  251 
    Suche in Google Scholar
  • 2b Mai A. Artico M. Ragno R. Sbardella G. Massa S. Musiu C. Mura M. Marturana F. Cadeddu A. Maga G. La Colla P. Bioorg. Med. Chem.  2005,  13:  2065 
    Suche in Google Scholar
  • 2c Ragno R. Mai A. Sbardella G. Artico M. Massa S. Musiu C. Mura M. Marturana F. Cadeddu A. La Colla P. J. Med. Chem.  2004,  47:  928 
    Suche in Google Scholar
  • 3 Mugnaini C. Alongi M. Togninelli A. Gevariya H. Brizzi A. Manetti F. Bernardini C. Angeli L. Tafi A. Bellucci L. Corelli F. Massa S. Maga G. Samuele A. Facchini M. Clotet-Codina I. Armand-Ugon M. Este JA. Botta M. J. Med. Chem.  2007,  50:  6580 
    CrossrefPubMedSuche in Google Scholar
  • 4 For an excellent review, see: von Angerer S. In Science of Synthesis   Yamamoto Y. Thieme; Stuttgart: 2004.  p.379 
  • 5a Kaneko T. Oizumi K. Katsura H. Nippon Kagaku Zasshi  1958,  79:  91 
    Suche in Google Scholar
  • 5b Trcek T. Vercek B. Acta Chim. Slov.  2005,  52:  171 
    Suche in Google Scholar
  • 5c Kepe V. Pozgan F. Golobic A. Polanc S. Kocevar M. J. Chem. Soc., Perkin Trans. 1  1998,  2813 
  • 5d El-Hawash SAM. Badawey E.-SAM. El-Ashmawey IM. Eur. J. Med. Chem.  2006,  41:  155 
    Suche in Google Scholar
  • 5e Vanden Eynde JJ. Labuche N. Van Haverbeke Y. Synth. Commun.  1997,  27:  3683 
    Suche in Google Scholar
  • 5f Cornforth JW. In The Chemistry of Penicillin   Clarke HT. Johnson JR. Robinson R. Princeton University Press; Princeton: 1949.  p.688 
  • 6a Tripathy PK. Mukerjee AK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1986,  25:  1059 
    Suche in Google Scholar
  • 6b Tikdari AM. Tripathy PK. Mukerjee AK. J. Chem. Soc., Perkin Trans. 1  1988,  1659 
  • 6c Tikdari AM. Tripathy PK. Mukerjee AK. Chem. Ind. (London)  1986,  825 
  • 7a Kappe CO. Angew. Chem. Int. Ed.  2004,  43:  6250 
    Suche in Google Scholar
  • 7b Wathey B. Tiemey J. Lidström P. Westman J. Drug Discovery Today  2002,  7:  373 
    Suche in Google Scholar
  • 7c Lidström P. Tierney J. Wathey B. Westman J. Tetrahedron  2001,  57:  9225 
    Suche in Google Scholar
  • 7d Caddick S. Fitzmaurice R. Tetrahedron  2009,  65:  3325 
    Suche in Google Scholar
  • 9 Aubert P. Knott EB. Williams LA. J. Chem. Soc.  1951,  2185 
    Crossref
  • 10 Matos MRPN. Gois PMP. Mata MLEN. Cabrita EJ. Afonso CAM. Synth. Commun.  2003,  33:  1285 
    CrossrefSuche in Google Scholar
  • 11a Dewey BT. Shasky HG. J. Am. Chem. Soc.  1941,  63:  3526 
    Suche in Google Scholar
  • 11b Iwai N. Fujii T. Nagura H. Wachi M. Kitazume T. Biosci., Biotechnol., Biochem.  2007,  71:  246 
    Suche in Google Scholar
  • 11c Laven G. Nilsson J. Stawinski J. Eur. J. Org. Chem.  2004,  5111 
  • 11d Paquette LA. Wittenbrook LS. Schreiber K. J. Org. Chem.  1968,  33:  1080 
    Suche in Google Scholar
8

CCDC 765698 contains the supplementary crystallographic data for the deposited structure. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Crystal data for compound 3a: C18H15N3O2S; Mr = 337.40; orthorhombic; Pca21; a = 17.284(5), b = 5.8034(17), c = 31.641(9) Å; V = 3173.8(16) ų; T = 100 K; Z = 8; D x = 1.412 Mg˙m-³; µ = 0.22 mm-¹; λ(Mo K α) = 0.71073 Å; F(000) = 1408; 6062 independent reflections (R int = 0.062), 4502 reflections with I > 2δ(I); refinement method, full-matrix least-squares refinement on F ²; R[F ²>2δ(F ²)] = 0.046, wR(F ²) = 0.101, S = 1.06.