Download PDF
Synlett 2011(11): 1623-1625  
DOI: 10.1055/s-0030-1260778
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of New o-Quinone Methides from β-Lapachone Analogues

Sabrina Baptista Ferreiraa, Daniel Tadeu Gomes Gonzagaa, Fernando de Carvalho da Silvaa, Katia Gomes de Lima Araújob, Vitor Francisco Ferreira*a
a Universidade Federal Fluminense, Instituto de Química, Departamento de Química Orgânica, 24020-141 Niterói, Rio de Janeiro, Brazil
Fax: +55(21)26292362; e-Mail: cegvito@vm.uff.br;
b Universidade Federal Fluminense, Faculdade de Farmácia, Departamento de Bromatologia, CEP 24241-000, Niterói, RJ, Brasil
Further Information

Publication History

Received 5 April 2011
Publication Date:
10 June 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

In this work, we synthesized six new o-quinone methides from β-lapachone analogues by treating β-lapachone with acetone and a catalytic amount of iodine under thermal conditions and microwave irradiation. The yields of isolated o-quinone methides ranged from 20-80%. During the reactions, the formation of α-pyran naphthoquinones was observed; the yields varied depending upon the substituent. The reactions using microwave irradiation were faster, but yields and selectivities did not change significantly.

Key words

β-lapachone - ortho-quinone methide - microwave - isomerization

    References

  • 1a Hussain H. Krohn K. Ahmad VU. Miana GA. Green IR. ARKIVOC  2007,  (ii):  145 
    Google Scholar
  • 1b da Silva MN. Ferreira VF. De Souza MCBV. Quim. Nova  2003,  26:  407 
    Google Scholar
  • 1c Pinto CN. Dantas AP. De Moura KCG. Emery FS. Polequevitch PF. Pinto MCFR. De Castro SL. Pinto AV. Arzneim.-Forsch./Drug Res.  2000,  50:  1120 
    Google Scholar
  • 1d Moon DO. Choi YH. Kim ND. Park YM. Kim GY. Int. Immunopharmacol.  2007,  7:  506 
    Google Scholar
  • 2a Fieser LF. Fieser M. J. Am. Chem. Soc.  1948,  70:  3215 
    Google Scholar
  • 2b Ferreira SB. Kaiser CR. Ferreira VF. Org. Prep. Proced. Int.  2009,  3:  211 
    Google Scholar
  • 3a Bourguignon SC. Castro HC. Santos DO. Alves CR. Ferreira VF. Gama IL. Silva FC. Seguis WS. Pinho RT. Exp. Parasitol.  2009,  122:  91 
    Google Scholar
  • 3b Emery FS. Silva RSF. De Moura KCG. Pinto MCFR. Amorim MB. Malta VRS. Santos RHAK. Honório M. Da Silva ABF. Pinto AV. Anais Acad. Brasil. Ciênc.  2007,  79:  29 
    Google Scholar
  • 3c da Silva FC. Jorqueira A. Gouvêa RM. De Souza MCBV. Howie RA. Wardell JL. Wardell SMSV. Ferreira VF. Synlett  2007,  3123 
    Google Scholar
  • 3d Pérez-Sacau E. Estévez-Braum A. Ravelo AG. Yapu DG. Turba AG. Helv. Chim. Acta  2005,  2:  264 
    Google Scholar
  • 3e Pérez-Sacau E. Díaz-Peñate RG. Estévez-Braun A. Ravelo AG. García-Castellano JM. Pardo L. Campillo M. J. Med. Chem.  2007,  50:  696 
    Google Scholar
  • 4 Ferreira SB. da Silva MN. Jorqueira A. de Souza MCBV. Pinto AV. Kaiser CR. Ferreira VF. Tetrahedron Lett.  2007,  48:  6171 
    CrossrefGoogle Scholar
  • 5 Ferreira SB. da Silva FC. Pinto AC. Gonzaga DTG. Ferreira VF. J. Heterocycl. Chem.  2009,  46:  1080 
    CrossrefGoogle Scholar
  • 6a Ferreira SB. Da Silva FC. Bezerra FAFM. Lourenço MCS. Kaiser CR. Pinto AC. Ferreira VF. Arch. Pharm. (Weinheim, Ger.)  2010,  343:  81 
    Google Scholar
  • 6b da Silva FC. Ferreira SB. Kaiser CR. Pinto AC. Ferreira VF. J. Braz. Chem. Soc.  2009,  20:  1478 
    Google Scholar