PDF herunterladen
Synthesis 2011(4): 593-598  
DOI: 10.1055/s-0030-1258404
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Selective Halogenation at Position 3 of 5-Hydroxy-2,7-dimethylchromone and Related Compounds

Pia Königsa, Björn Rinkera, Gregor Schnakenburgb, Martin Niegerc, Siegfried R. Waldvogel*a,d
a Kekulé Institute for Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Str.1, 53121 Bonn, Germany
b Institute of Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str.1, 53121 Bonn, Germany
c Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55, 00014 Helsinki, Finland
d Institute for Organic Chemistry, Johannes-Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(6131)3926777; e-Mail: waldvogel@uni-mainz.de;
Weitere Informationen

Publikationsverlauf

Received 25 August 2010
Publikationsdatum:
11. Januar 2011 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The core moiety of several natural products referred in the literature as altechromone A can be selectively brominated or iodinated at position 3 despite the adjacent phenolic moiety. This method is extended to more elaborated 5-hydroxychromones exhibiting additional multiple bonds.

Key words

halogenation - heterocycles - chromones - iodination - bromination

    References

  • 1a Saengchantara ST. Wallace TW. Nat. Prod. Rep.  1986,  3:  465 
    Google Scholar
  • 1b Houghton PJ. Stud. Nat. Prod. Chem.  2000,  21:  123 
    Google Scholar
  • 1c Sagrera G. Seoane G. Synthesis  2010,  2776 
    Google Scholar
  • 1d Huang Z. Yang R. Guo Z. She Z. Lin Y. Chem. Nat. Compd.  2010,  46:  15 
    Google Scholar
  • 1e Zhang HW. Song YC. Tan RX. Nat. Prod. Rep.  2006,  23:  753 
    Google Scholar
  • 1f Hepworth JD. Heron MB. Gabutt CD. In Comprehensive Heterocyclic Chemistry II   1st ed., Vol. 5:  Katritzky AR. Rees CW. Scriven EFV. Pergamon Press; Oxford: 1996.  p.427 
    Google Scholar
  • 2a Horton DA. Bourne GT. Smythe ML. Chem. Rev.  2003,  103:  893 
    Google Scholar
  • 2b Geen GR. Evans JM. Vong AK. In Comprehensive Heterocyclic Chemistry II   1st ed., Vol. 5:  Katritzky AR. Rees CW. Scriven EFV. Pergamon Press; Oxford: 1996.  p.469 
    Google Scholar
  • See, for example:
  • 3a Nakazumi H. Maeda K. Yagi S. Kitao T. J. Chem. Soc., Chem. Commun.  1992,  1188 
    Google Scholar
  • 3b Karapire C. Kolancilar H. Oyman Ü. Icli SJ. Photochem. Photobiol. A  2002,  153:  173 
    Google Scholar
  • 3c Walenzyk T. Carola C. Buchholz H. König B. Tetrahedron  2005,  61:  7366 
    Google Scholar
  • 4 Wang H. Gloer JB. Tetrahedron Lett.  1995,  36:  5847 
    CrossrefGoogle Scholar
  • 5 Kong F. Carter GT. Tetrahedron Lett.  2003,  44:  3119 
    CrossrefGoogle Scholar
  • 6 Sassa T. Kachi H. Nukina M. J. Antibiot.  1985,  38:  439 
    CrossrefGoogle Scholar
  • 7 Ahluwalia VK. Kumar D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1976,  14:  326 
    Google Scholar
  • 8 Kimura Y. Mizuno T. Nakajima H. Hamasaki T. Biosci. Biotechnol. Biochem.  1992,  56:  1664 
    CrossrefGoogle Scholar
  • 9a Gu W. Ge HM. Song Y. C. Ding H. Zhu HL. Zhao XA. Tan RX. J. Nat. Prod.  2007,  70:  114 
    Google Scholar
  • 9b Shushni MAM. Mentel R. Lindequist U. Jansen R. Chem. Biodiversity  2009,  6:  127 
    Google Scholar
  • 9c Gu W. World J. Microbiol. Biotechnol.  2009,  25:  1677 
    Google Scholar
  • 10 Königs P. Rinker B. Maus L. Nieger M. Rheinheimer J. Waldvogel SR. J. Nat. Prod.  2010,  73:  2064 
    CrossrefGoogle Scholar
  • 11 Arndt F. Ber. Dtsch. Chem. Ges.  1925,  58:  1612 
    CrossrefGoogle Scholar
  • 12 Offe HA. Ber. Dtsch. Chem. Ges.  1938,  71:  1837 
    CrossrefGoogle Scholar
  • 13 Winter CW. Hamilton CS. J. Am. Chem. Soc.  1952,  74:  3999 
    CrossrefGoogle Scholar
  • 14a Merchant JR. Rege DV. Tetrahedron  1971,  27:  4837 
    Google Scholar
  • 14b Lin C.-F. Duh T.-H. Lu W.-D. Lee J.-L. Lee C.-Y. Chen C.-C. Wu M.-J. J. Chin. Chem. Soc.  2004,  51:  183 
    Google Scholar
  • 14c Kamla C. Rastogi MK. Kapoor RP. Garg CP. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1978,  16:  417 
    Google Scholar
  • 15a Bird TGC. Brown BR. Stuart IA. Tyrrell AWR. J. Chem. Soc., Perkin Trans. 1  1983,  1831 
    Google Scholar
  • 15b Miyake M. Nishino S. Nishimura A. Sasaki M. Chem. Lett.  2007,  36:  522 
    Google Scholar
  • 15c Fitzmaurice RJ. Etheridge ZC. Jumel E. Woolfson DN. Caddick S. Chem. Commun.  2006,  4814 
    Google Scholar
  • 15d Zhou Z. Zhao P. Huang W. Guangfu Y. Adv. Synth. Catal.  2006,  348:  63 
    Google Scholar
  • 15e Mazumdar AKD. Saha GC. Sinha TK. Banerji KD. J. Indian Chem. Soc.  1984,  61:  996 
    Google Scholar
  • 15f Joo YH. Kim JK. Synth. Commun.  1998,  28:  4287 
    Google Scholar
  • 15g Rho HS. Ko B.-S. Kim HK. Ju Y.-S. Synth. Commun.  2002,  32:  1303 
    Google Scholar
  • 16a Zhang FJ. Li YL. Synthesis  1993,  565 
    Google Scholar
  • 16b Costa AMBSRCS. Dean FM. Jones MA. Varma RS. J. Chem. Soc., Perkin Trans. 1  1985,  799 
    Google Scholar
  • 17a Jagadeesh SG. Krupadanam DLD. Srimannarayana G. Synth. Commun.  1998,  28:  3827 
    Google Scholar
  • 17b Zagorevskii VA. Tsvetkova ID. Orlova EK. Chem. Heterocycl. Compd.  1967,  3:  624 
    Google Scholar
  • 17c Dike SY. Mahalingam M. Synth. Commun.  1989,  19:  3443 
    Google Scholar
  • 17d Yamauchi M. Katayama S. Nakashita Y. Watanabe T. Synthesis  1981,  33 
    Google Scholar
  • 18a Santos CMM. Silva AMS. Cavaleiro JAS. Synlett  2005,  3095 
    Google Scholar
  • 18b Ibrahim SS. Ind. Eng. Chem. Res.  2001,  40:  37 
    Google Scholar
  • 18c Gammill RB. Synthesis  1979,  901 
    Google Scholar
  • 18d Nohara A. Ukawa K. Sanno Y. Tetrahedron  1974,  30:  3563 
    Google Scholar
  • 19a Zhou C. Dubrovsky AV. Larock RC. J. Org. Chem.  2006,  71:  1626 
    Google Scholar
  • 19b Likhar PR. Subhas MS. Roy M. Roy S. Kantam ML. Helv. Chim. Acta  2008,  91:  259 
    Google Scholar
  • 20a Waldvogel SR. Wehming K. In Science of Synthesis   Vol. 31:  Ramsden CA. Thieme; Stuttgart: 2007.  p.235 
    Google Scholar
  • 20b Waldvogel SR. In Science of Synthesis Knowledge Updates   Vol. 2010/1:  Ramsden CA. Thomas EJ. Thieme; Stuttgart: 2010.  p.487 
    Google Scholar
  • 21a Still WC. Gennari C. Tetrahedron Lett.  1983,  24:  4405 
    Google Scholar
  • 21b Motoyoshiya J. Kusaura T. Kokin K. Yokoya S. Takaguchi Y. Narita S. Aoyama H. Tetrahedron  2001,  57:  1715 
    Google Scholar