Synthesis 2009(4): 587-590  
DOI: 10.1055/s-0028-1083312
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Route to 1-Vinylpyrrole-2-carbaldehydes

Al’bina I. Mikhaleva, Andrey V. Ivanov, Elena V. Skital’tseva, Igor’ A. Ushakov, Alexander M. Vasil’tsov, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
Further Information

Publication History

Received 9 September 2008
Publication Date:
12 January 2009 (online)

Abstract

1-Vinylpyrroles are formylated by the N,N-dimethyl­formamide/oxalyl chloride reagent system (CH2Cl2, r.t., 40 min) to give the corresponding 1-vinylpyrrole-2-carbaldehydes in yields up to 97%.

    References

  • 1 Brandsma L. Eur. J. Org. Chem.  2001,  4569 
  • 2a Mikhaleva AI. Schmidt EYu. In Selected Methods for Synthesis and Modification of Heterocycles   Kartsev VG. IBS Press; Moscow: 2002.  p.331 
  • 2b Romila D. Schlingmann G. Valerie S. Xidong F. Carter G. J. Nat. Prod.  2005,  68:  277 
  • 3a Hue T. Scott AI. Tetrahedron Lett.  1998,  39:  6651 
  • 3b Sessler JL. Roznyatovskiy V. Pantos JD. Borisova NE. Reshetova MD. Lynch VM. Krustalev VN. Ustynyuk JA. Org. Lett.  2005,  7:  5277 
  • 4 Hunt JT. Mitt T. Borzilleri R. Gullo-Brown J. Fargnolli J. Fink B. Han WC. Mortillo S. Vite G. Wautlet B. Wong T. Yu C. Zheng X. Bhide R. J. Med. Chem.  2004,  47:  4054 
  • 5a Furuta H. Maeda H. Furuta T. Osuka A. Org. Lett.  2000,  2:  187 
  • 5b Wiehe A. Ruppa C. Senge MO. Org. Lett.  2002,  4:  3807 
  • 6 Bouérat L. Fensholdt J. Liang X. Havez S. Nielsen SF. Hansen JR. Bolvig S. Andersson C. J. Med. Chem.  2005,  48:  5412 
  • 7 Mutsui T. Kitamura A. Kimora M. To T. Sato A. Hirao I. Yokoyama S. J. Am. Chem. Soc.  2003,  125:  5298 
  • 8 Westmoreland I. Synthetic Page  2005,  224 ; see http://www.syntheticpages.org/pages/224
  • 9a Simionescu CI. Grigoras M. Cianga I. Diaconu I. Farcas A. Polym. Bull.  1994,  32:  257 
  • 9b Simionescu CI. Grovu-Ivanoiu M. Grigoras M. Cianga I. Angew. Makromol. Chem.  1994,  221:  103 
  • 10a Nagaraj RH. Monnier VM. Biochim. Biophys. Acta  1995,  1253:  75 
  • 10b Hofmann T. J. Agric. Food Chem.  1998,  46:  3902 
  • 11 Utzman CM. Lederer MO. Carbohydr. Res.  2000,  325:  157 
  • 12 Zhang H. Larock RC. J. Org. Chem.  2002,  67:  7048 
  • 13 Pavlov PA. Russ. J. Org. Chem.  2001,  37:  1310 
  • 14 Settambolo R. Marani M. Caiazzo A. J. Org. Chem.  1998,  63:  10022 
  • 15a Trofimov BA. Mikhaleva AI. N-Vinylpyrroles   Nauka; Novosibirsk: 1984.  p.264 ; in Russian
  • 15b Bean GP. In The Chemistry of Heterocyclic Compounds. Pyrroles   Part 2:  Jones RA. Wiley Interscience; New York: 1992.  p.105 
  • 15c Trofimov BA. In Pyrroles   Part 1:  Jones RA. Wiley; New York: 1992.  p.131 
  • 15d Abele E. Lukevics E. Heterocycles  2000,  53:  2285 
  • 15e Gilchrist TL. J. Chem. Soc., Perkin Trans. 1  2001,  2491 
  • 16 Mikhaleva AI. Zaitsev AB. Ivanov AV. Schmidt EYu. Vasil’tsov AM. Trofimov BA. Tetrahedron Lett.  2006,  47:  3693 
  • 17a Vatsuro KV. Mishchenko GL. Named Reactions in Organic Chemistry   Khimiya; Moscow: 1976.  p.115 ; in Russian
  • 17b Beer PD. Cheetham AG. Drew MGB. Fox OD. Hayes EJ. Rolls TD. Dalton Trans.  2003,  603 
  • 18a Barnett GH. Anderson HJ. Loader CE. Can. J. Chem.  1980,  58:  409 
  • 18b Faber K. Anderson HJ. Loader CE. Daley AS. Can. J. Chem.  1984,  62:  1046 
  • 18c Meth-Cohn O. Ashton M. Tetrahedron Lett.  2000,  41:  2749 
  • 19a Zoller G, Beyerle R, and Schindler U. inventors; U.S. Pat.  4,966,901.  ; Chem. Abstr. 1990, 113, 6150x
  • 19b Zoller G, Beyerle R, and Schindler U. inventors; US Patent  5043348.  ; Chem. Abstr. 1989, 110, 135078
  • 19c Liebeskind LS, and Wansheng L. inventors; US Patent 6441194  B1.  ; Chem. Abstr. 2002, 134, 311103
  • 20 Mikhaleva AI. Ivanov AV. Vasil’tsov AM. Ushakov IA. Ma JS. Yang G. Khim. Geterotsikl. Soedin.  2008,  1384 
  • 21 Kantlehner W. Eur. J. Org. Chem.  2003,  2530 ; and references cited therein