Download PDF
Synthesis 2010(17): 2985-2989  
DOI: 10.1055/s-0030-1258177
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3-Substituted 1-Thioacyl- and 1-Thiocarbamoylindoles from α-Substituted 2-Isocyanato-β-methoxystyrenes

Shuhei Fukamachi, Seiki Fujita, Kazuya Murahashi, Hisatoshi Konishi, Kazuhiro Kobayashi*
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
Further Information

Publication History

Received 19 March 2010
Publication Date:
12 July 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

3-Aryl-1-thioacylindoles were prepared by treating α-aryl-2-isothiocyanato-β-methoxystyrenes with organolithiums or Grignard reagents, followed by hydriodic acid catalyzed cyclization of the resulting adducts. A one-pot synthesis of 1-thiocarbamoylindoles was achieved by hydriodic acid mediated cyclization of the corresponding thiourea intermediates, prepared from α-substituted 2-isothiocyanato-β-methoxystyrenes and secondary amines.

Key words

heterocycles - indoles - cyclizations - isothiocyanates - organometallic reagents

    References

  • 1 Kobayashi K. Fujita S. Fukamachi S. Konishi H. Synthesis  2009,  3378 
    Article in Thieme ConnectGoogle Scholar
  • 2 A synthesis of 1-acylindoles by hydrochloric acid-mediated cyclization of N-[2-(2-ethoxyvinyl)phenyl]alkyl amides has been reported, see: Satoh M. Miyaura N. Suzuki A. Synthesis  1987,  373 
    Article in Thieme ConnectGoogle Scholar
  • For recent reports, see:
  • 3a Tyrrell E. Whiteman L. Williams N. Synthesis  2009,  829 
    Google Scholar
  • 3b Bernini R. Cacchi S. Fabrizi C. Filsti E. Sferraze A. Synlett  2009,  1480 
    Google Scholar
  • 3c Hsieh TH. Dong VM. Tetrahedron  2009,  65:  3062 
    Google Scholar
  • 3d Denmark SE. Baird JD. Tetrahedron  2009,  65:  3120 
    Google Scholar
  • 3e Hisler K. Commeyreuc AGJ. Zhou S.-z. Murphy JA. Tetrahedron Lett.  2009,  50:  3290 
    Google Scholar
  • 3f Kobayashi K. Iitsuka D. Fukamachi S. Konishi H. Tetrahedron  2009,  65:  7523 
    Google Scholar
  • 3g Muzalevskiy VM. Nenajdenko VG. Shastin AV. Balenkova ES. Haufe G. Tetrahedron  2009,  65:  7553 
    Google Scholar
  • 3h Ackermann L. Sandmann R. Schinkel M. Kondrashov MV. Tetrahedron  2009,  65:  8930 
    Google Scholar
  • 3i Zhou L. Doyle MP. J. Org. Chem.  2009,  74:  9222 ; and pertinent references cited in these papers
    Google Scholar
  • 4 Wang W. Rattananakin P. Goekjian PG. J. Carbohydr. Chem.  2003,  22:  743 
    CrossrefGoogle Scholar
  • 5 Doss SH. Mohareb RM. Elmegeed GA. Luoca NA. Pharmazie  2003,  58:  607 
    Google Scholar
  • 6 Flitsch W. Niehoff A. Liebigs Ann. Chem.  1989,  239 
    CrossrefGoogle Scholar
  • 7 Fujiwara S. Shin-Ike T. Sonoda N. Aoki M. Okada K. Miyoshi N. Kambe N. Tetrahedron Lett.  1991,  32:  3503 
    CrossrefGoogle Scholar
  • 8 Kobayashi K. Yoneda K. Miyamoto K. Morikawa O. Konishi H. Tetrahedron  2004,  60:  11639 
    CrossrefGoogle Scholar