Download PDF
Synthesis 2011(3): 413-418  
DOI: 10.1055/s-0030-1258386
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient and Highly Selective Method for the Synthesis of 4-Iodo-3-substituted 1H-Isoselenochromenes and -isothiochromenes

Caroline C. Schneidera, Cristiani Bortolattoa, Davi F. Backb, Paulo H. Menezesc, Gilson Zeni*a
a Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria, Rio Grande do Sul CEP 97105-900, Brazil
Fax: +55(55)32208978; e-Mail: gzeni@pq.cnpq.br;
b Laboratório de Materiais Inorgânicos, CCNE, UFSM, Santa Maria, Rio Grande do Sul, 97105-900, Brazil
c Universidade Federal de Pernambuco, Departamento Química Fundamental, Recife, Pernambuco 50670-901, Brazil
Further Information

Publication History

Received 5 October 2010
Publication Date:
23 December 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

We present here our results on the preparation of 2-alkynylbenzyl selenide and sulfide derivatives via Sonogashira cross-coupling of benzyl chalcogenides with different alkynes. This cross-coupling reaction proceeded cleanly under mild conditions and was performed with propargyl alcohol as well as alkyl- and arylalkynes. Subsequent electrophilic-cyclization reaction of the 2-alkynylbenzyl selenide and sulfide derivatives using iodine as an electrophilic source gave 4-iodo-3-substituted 1H-isoselenochromenes and -isothiochromenes in moderate yields. The unique product obtained during the course of this cyclization contained a six-membered ring which was confirmed by X-ray diffraction analysis.

Key words

selenides - isochromenes - electrophilic cyclization - heterocycles

    References

  • 1a Sebille S. Gall D. de Tullio P. Florence X. Lebrun P. Pirotte B. J. Med. Chem.  2006,  49:  4690 
    Google Scholar
  • 1b Madrid PB. Liou AP. DeRisi JL. Guy RK. J. Med. Chem.  2006,  49:  4535 
    Google Scholar
  • 1c Heinrich T. Böttcher H. Schiemann K. Holzemann G. Schwarz M. Bartoszyk GD. Amsterdam C. Greiner HE. Seyfried CA. Bioorg. Med. Chem.  2004,  12:  4843 
    Google Scholar
  • 1d Tang L. Yu J. Leng Y. Feng Y. Yang Y. Ji R. Bioorg. Med. Chem. Lett.  2003,  13:  3437 
    Google Scholar
  • 2a Zeni G. Larock RC. Chem. Rev.  2004,  104:  2285 
    Google Scholar
  • 2b Zeni G. Larock RC. Chem. Rev.  2007,  107:  303 
    Google Scholar
  • 4a Hua G. Fuller AL. Slawin AMZ. Woollins JD. Eur. J. Org. Chem.  2010,  2607 
    Google Scholar
  • 4b Hua G. Henry JB. Li Y. Mount AR. Slawin AMZ. Woollins JD. Org. Biomol. Chem.  2010,  8:  1655 
    Google Scholar
  • 4c Hua G. Zhang Q. Li Y. Slawin AMZ. Woollins JD. Tetrahedron  2009,  65:  6074 
    Google Scholar
  • 4d Hua G. Li Y. Fuller AL. Slawin AMZ. Woollins JD. Eur. J. Org. Chem.  2009,  1612 
    Google Scholar
  • 4e Narender M. Reddy MS. Kumar VP. Srinivas B. Sridhar R. Venkata Y. Nageswar D. Rao KR. Synthesis  2007,  3469 
    Google Scholar
  • 4f Narender M. Reddy MS. Kumar VP. Reddy VP. Nageswar YVD. Rao KR. J. Org. Chem.  2007,  72:  1849 
    Google Scholar
  • 5 Meotti FC. Silva DO. Santos ARS. Zeni G. Rocha JBT. Nogueira CW. Environ. Toxicol. Pharmacol.  2003,  37:  37 
    Google Scholar
  • 6 Gonçalves CEP. Araldi D. Panatieri RB. Rocha JBT. Zeni G. Nogueira CW. Life Sci.  2005,  76:  2221 
    CrossrefGoogle Scholar
  • 7a Zeni G. Lüdtke DS. Nogueira CW. Panatieri RB. Braga AL. Silveira CC. Stefani HA. Rocha JBT. Tetrahedron Lett.  2001,  42:  8927 
    Google Scholar
  • 7b Zeni G. Nogueira CW. Panatieri RB. Silva DO. Menezes PH. Braga AL. Silveira CC. Stefani HA. Rocha JBT. Tetrahedron Lett.  2001,  42:  7921 
    Google Scholar
  • 8a Srivastava PC. Robins RK. J. Med. Chem.  1983,  26:  445 
    Google Scholar
  • 8b Streeter DG. Robins RK. Biochem. Biophys. Res. Commun.  1983,  115:  544 
    Google Scholar
  • 8c Kirsi JJ. North J. McKernan PA. Murray BK. Canonico PG. Huggins JW. Srivastava PC. Robins RK. Antimicrob. Agents Chemother.  1983,  24:  353 
    Google Scholar
  • 9a Hessian KO. Flynn BL. Org. Lett.  2006,  8:  243 
    Google Scholar
  • 9b Sniady A. Wheeler KA. Dembinski R. Org. Lett.  2005,  7:  1769 
    Google Scholar
  • 9c Alves D. Luchese C. Nogueira CW. Zeni G. J. Org. Chem.  2007,  72:  6726 
    Google Scholar
  • 9d Yue D. Yao T. Larock RC. J. Org. Chem.  2005,  70:  10292 
    Google Scholar
  • 10a Morita Y. Ohmae T. Matsuda S. Toda F. Nakasuji K. Chem. Lett.  1993,  443 
    Google Scholar
  • 10b Mohsine A. Christiaens L. Heterocycles  1996,  43:  2567 
    Google Scholar
  • 10c Sashida H. Ohyanagi K. Minoura M. Akiba K. J. Chem. Soc., Perkin Trans. 1  2002,  606 
    Google Scholar
  • 11a Manarin F. Roehrs JA. Gay RM. Brandão R. Menezes PH. Nogueira CW. Zeni G. J. Org. Chem.  2009,  74:  2153 
    Google Scholar
  • 11b Godoi B. Sperança A. Back DF. Brandão R. Nogueira CW. Zeni G. J. Org. Chem.  2009,  74:  3469 
    Google Scholar
  • 11c Stein AL. Alves D. Rocha JT. Nogueira CW. Zeni G. Org. Lett.  2008,  10:  4983 
    Google Scholar
  • 11d Alves D. Prigol M. Nogueira CW. Zeni G. Synlett  2008,  914 
    Google Scholar
  • 11e Alves D. Luchese C. Nogueira CW. Zeni G. J. Org. Chem.  2007,  72:  6726 
    Google Scholar
  • 12 Uemura S. Fukuzawa S. J. Am. Chem. Soc.  1983,  105:  2748 
    CrossrefGoogle Scholar
  • 13a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett.  1975,  16:  4467 
    Google Scholar
  • 13b Najera C. Sansano JM. Angew. Chem. Int. Ed.  2009,  48:  2452 
    Google Scholar
  • 13c Chinchilla R. Najera C. Chem. Rev.  2007,  107:  864 
    Google Scholar
  • 13d Vicente J. Abad JA. Lopez-Serrano J. Jones PG. Najera C. Botella-Segura L. Organometallics  2005,  24:  5044 
    Google Scholar
  • 13e Chinchilla R. Najera C. Yus M. Chem. Rev.  2004,  104:  2667 
    Google Scholar
3

Special issue: Heterocycles, Chem. Rev. 2004, 104, 2125.