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Synthesis 2004(16): 2736-2742  
DOI: 10.1055/s-2004-831244
PAPER
© Georg Thieme Verlag Stuttgart · New York

Silica-Assisted Reactions of Pyrroles with 1-Acyl-2-bromoacetylenes

Zinaida V. Stepanova, Lubov’ N. Sobenina*, Al’bina I. Mikhaleva, Igor’ A. Ushakov, Nina N. Chipanina, Valentina N. Elokhina, Vladimir K. Voronov, Boris A. Trofimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia
Fax: +7(3952)419346; e-Mail: sobenina@irioch.irk.ru;
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Publikationsverlauf

Received 28 June 2004
Publikationsdatum:
22. September 2004 (online)

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Abstract

Pyrroles react with 1-acyl-2-bromoacetylenes at room temperature on silica to give 2-acyl-1,1-di(pyrrol-2-yl)ethenes as major products in yields of up to 60%. Under reaction conditions employed, the intermediates (E)-2-(2-acyl-1-bromoethenyl)pyrroles (3-11% isolated yields) either readily exchange the bromine atom for the pyrrole molecule or eliminate HBr to afford 2-(2-acylethynyl)pyrroles, which can be isolated in 9-22% yields by chromatography of the reaction mixture on Al2O3.

Key words

pyrroles - 1-acyl-2-bromoacetylenes - 2-(2-acyl-1-bromoethenyl)pyrroles - 2-acyl-1,1-di(pyrrol-2-yl)ethenes - 2-(2-acylethynyl)pyrroles - silica

    References

  • 1 Banerjee AK. Mimo MSL. Vegas WJV. Russ. Chem. Rev.  2001,  70:  971 ; Usp. Khim. 2001, 70, 1094
    CrossrefGoogle Scholar
  • 2 Basiuk VA. Russ. Chem. Rev.  1995,  64:  1003 ; Usp. Khim. 1995, 64, 1073
    CrossrefGoogle Scholar
  • 3 Veselovskii VV. Gybin AS. Lozanova AV. Moiseenkov AM. Smit WA. Bull. Acad. Sci. USSR Div. Chem. Sci.  1990,  39:  94 ; Izv. AN SSSR. Ser. Khim. 1990, 107; Chem. Abstr. 1990, 113, 77723
    CrossrefGoogle Scholar
  • 4 Veselovskii VV. Gybin AS. Lozanova AV. Moiseenkov AM. Smit WA. Caple R. Tetrahedron  1988,  29:  175 
    CrossrefGoogle Scholar
  • 5 Sviridova LA. Golubeva GA. Lescheva MF. Mizgunov AV. Chem. Heterocycl. Compd.  1995,  1441 ; Khim. Geterotsikl. Soedin. 1995, 1489
    Google Scholar
  • 6 Yong ZJ. Yasuda N. Furuno H. Inanaga J. Tetrahedron Lett.  2003,  44:  8765 
    CrossrefGoogle Scholar
  • 7a Trofimov BA. Stepanova ZV. Sobenina LN. Mikhaleva AI. Ushakov IA. Toryashinova D.-SD. Chem. Heterocycl. Compd.  1999,  35:  1107 ; Khim. Geterotsikl. Soedin. 1999, 1253
    Artikel in Thieme ConnectGoogle Scholar
  • 7b Trofimov BA. Stepanova ZV. Sobenina LN. Mikhaleva AI. Ushakov IA. Elokhina VN. Synthesis  2001,  1878 
    Artikel in Thieme ConnectGoogle Scholar
  • 8 Stepanova ZV. Sobenina LN. Mikhaleva AI. Ushakov IA. Elokhina VN. Vorontsov II. Antipin MY. Trofimov BA. Russ. J. Org. Chem.  2003,  39:  1636 ; Zh. Org. Khim. 2003, 39, 1705
    CrossrefGoogle Scholar
  • 9a Gossauer A. In Houben-Weyl, Methoden der Organischen Chemie   Part 1, Vol E6a:  Thieme Verlag; Stuttgart: 1994.  p.556-798  
    CrossrefGoogle Scholar
  • 9b Melvin MS. Ferguson DC. Lindquist N. Manderville RA. J. Org. Chem.  1999,  62:  6861 
    CrossrefGoogle Scholar
  • 9c Fürstner A. Angew. Chem. Int. Ed.  2003,  42:  3582 
    CrossrefGoogle Scholar
  • 9d Tanade M. Shibata Y. Maeda M. Sasaki S. Heterocycles  2004,  63:  29 
    CrossrefGoogle Scholar
  • 10a Scherer M. Sessler JL. Gebauer A. Lynch V. Chem. Commun.  1998,  85 
    CrossrefGoogle Scholar
  • 10b Lee C.-F. Yang L.-M. Hwu T.-Y. Feng A.-S. Tseng J.-C. Luh T.-Y. J. Am. Chem. Soc.  2000,  122:  4992 
    CrossrefGoogle Scholar
  • 10c Denuault G. Gale PA. Hursthouse MB. Light ME. Warriner CN. New. J. Chem.  2002,  26:  811 
    CrossrefGoogle Scholar
  • 11 Sobenina LN. D’yachkova SG. Stepanova ZV. Toryashinova D.-SD. Albanov AI. Ushakov IA. Demenev AP. Mikhaleva AI. Trofimov BA. Russ. J. Org. Chem.  1999,  35:  916 ; Zh. Org. Khim. 1999, 35, 941
    Google Scholar
  • 12 Diekstein JI. Miller SI. The Chemistry of the Carbon-Carbon Triple Bond   Part 2:  Patai S. Wiley; New York: 1978.  p.911 
    Google Scholar
  • 13a Nakhmanovich AS. Komarova TN. Lopyrev VA. Russ. J. Org. Chem.  2000,  36:  1551 ; Zh. Org. Khim. 2000, 36, 1599
    CrossrefGoogle Scholar
  • 13b Glotova TN. Komarova TN. Nakhmanovich AS. Lopyrev VA. Russ. Chem. Bull., Int. Ed.  2000,  49:  1917 ; Izv. RAN. Ser. Khim. 2000, 1947
    CrossrefGoogle Scholar
  • 13c Elokhina VN. Nakhmanovich AS. Larina LI. Shishkin OV. Baumer VN. Lopyrev VA. Russ. Chem. Bull., Int. Ed.  1999,  48:  1516 ; Izv. RAN. Ser. Khim. 1999, 1536
    CrossrefGoogle Scholar
  • 13d Nizovtseva TV. Komarova TN. Nakhmanovich AS. Lopyrev VA. Chem. Heterocycl. Compd.  2002,  38:  1134 ; Khim. Geterotsikl. Soedin. 2002, 1293
    CrossrefGoogle Scholar
  • 13e Sobenina LN. Demenev AP. Mikhaleva AI. Ushakov IA. Afonin AV. Petrova OV. Elokhina VN. Volkova KA. Toryashinova D.-SD. Trofimov BA. Sulfur Lett.  2002,  25:  87 
    CrossrefGoogle Scholar
  • 13f Sobenina LN. Demenev AP. Mikhaleva AI. Ushakov IA. Afonin AV. D’yachkova SG. Beskrylaya EA. Oparina LA. Elokhina VN. Volkova KA. Petrova OV. Trofimov BA. Chem. Heterocycl. Compd.  2002,  38:  86 ; Khim. Geterotsikl. Soedin. 2002, 95
    CrossrefGoogle Scholar
  • 14 Chipanina NN. Turchaninov VK. Vorontsov JJ. Antipin MY. Stepanova ZV. Sobenina LN. Mikhaleva AI. Trofimov BA. Russ. Chem. Bull., Int. Ed.  2002,  51:  111 ; Izv. RAN. Ser. Khim. 2002, 107
    CrossrefGoogle Scholar
  • 15 Chipanina NN. Stepanova ZV. Gavrilova GA. Sobenina LN. Mikhaleva AI. Russ. Chem. Bull., Int. Ed.  2000,  49:  1914 ; Izv. RAN. Ser. Khim. 2000, 1945
    CrossrefGoogle Scholar
  • 16a Wagner G. Wutrich K. J. Mol. Biol.  1982,  155:  347 
    Google Scholar
  • 16b Nagayama K. Kumar A. Wüthrich K. Ernst RR. J. Magn. Reson.  1980,  40:  321 
    Google Scholar
  • 17a Bodenhausen G. Ruben DJ. Chem. Phys. Lett.  1980,  69:  185 
    CrossrefGoogle Scholar
  • 17b Bax A. Summers MF. J. Am. Chem. Soc.  1986,  108:  2093 
    CrossrefGoogle Scholar
  • 18a Trofimov BA. Geteroatomnye Proizvodnye Atsetylene. Novye Polyphunctional’nye Monomery, Reagenty i Poluproducty (Heteroatomic Derivatives of Acetylene. New Polyfunctional Monomers, Reagents and Intermediate Products)   Nauka; Moskva: 1981. 
    Google Scholar
  • 18b Trofimov BA. Mikhaleva AI. N-Vinilpyrroli   Nauka; Novosibirsk: 1984. 
    Google Scholar
  • 18c Trofimov BA. Advanced Heterocyclic Chemistry   Academic Press; New York: 1990. 
    Google Scholar
  • 18d Bean G. The Synthesis of 1H-Pyrroles, The Synthesis and the Chemical and the Physical Aspects Pyrrole Ring   Part 1:  Wiley; New York: 1990. 
    Google Scholar
  • 18e Tedeschi RJ. Encyclopedia of Physical Science and Technology   Academic Press; San Diego: 1992. 
    Google Scholar
  • 18f Trofimov BA. Pyrroles, The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles   Part 2:  Wiley; New York: 1992. 
    Google Scholar