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Synlett 2011(7): 1015-1017  
DOI: 10.1055/s-0030-1259930
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Indium-Catalyzed Synthesis of Furans and Pyrroles via Cyclization of α-Propargyl-β-keto Esters

Hayato Tsuji*, Ken-ichi Yamagata, Yasuyuki Ueda, Eiichi Nakamura*
Department of Chemistry, School of Science, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Fax: +81(3)58006889; e-Mail: nakamura@chem.s.u-tokyo.ac.jp;
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Publikationsverlauf

Received 2 December 2010
Publikationsdatum:
29. März 2011 (online)

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Abstract

In(OTf)3 or In(NTf2)3 effectively catalyze the cyclo­isomerization reaction of α-propargyl-β-keto esters and their imine analogues to afford trisubstituted furans and pyrroles, respectively. Both terminal and internal alkynes take part in the reaction with good functional-group compatibility in the presence of only a small amount of the catalyst.

Key words

indium catalyst - keto ester - cyclization - furan - pyrrole

    References

  • For reviews, see:
  • 1a Cintas P. Synlett  1995,  1087 
    Google Scholar
  • 1b Li C.-J. Chan T.-H. Tetrahedron  1999,  55:  11149 
    Google Scholar
  • 1c Ranu BC. Eur. J. Org. Chem.  2000,  2347 
    Google Scholar
  • 1d Podlech J. Maier TC. Synthesis  2003,  633 
    Google Scholar
  • 1e Nair V. Ros S. Jayan CN. Pillai BS. Tetrahedron  2004,  60:  1959 
    Google Scholar
  • 1f Augé J. Lubin-Germain N. Uziel J. Synthesis  2007,  1739 
    Google Scholar
  • 1g Yadav JS. Antony A. George J. Reddy BV. Eur. J. Org. Chem.  2010,  591 
    Google Scholar
  • 2 For example, see: Haddad TD. Hirayama LC. Singaram B. J. Org. Chem.  2010,  75:  642 
    CrossrefGoogle Scholar
  • 3 For example, see: Muñoz-Muñiz O. Quintanar-Audelo M. Juaristi E. J. Org. Chem.  2003,  68:  1622 
    CrossrefGoogle Scholar
  • 4 Hosomi A. Endo M. Sakurai H. Chem. Lett.  1976,  941 
    Google Scholar
  • 5a Nakamura M. Endo K. Nakamura E. J. Am. Chem. Soc.  2003,  125:  13002 
    Google Scholar
  • 5b Nakamura M. Endo K. Nakamura E. Org. Lett.  2005,  7:  3279 
    Google Scholar
  • 5c Nakamura M. Endo K. Nakamura E. Adv. Synth. Catal.  2005,  347:  1681 
    Google Scholar
  • 5d Endo K. Hatakeyama T. Nakamura M. Nakamura E. J. Am. Chem. Soc.  2007,  129:  5264 
    Google Scholar
  • 5e Tsuji H. Yamagata K.-i. Itoh Y. Endo K. Nakamura M. Nakamura E. Angew. Chem. Int. Ed.  2007,  46:  8060 
    Google Scholar
  • 5f Tsuji H. Fujimoto T. Endo K. Nakamura M. Nakamura E. Org. Lett.  2008,  10:  1219 
    Google Scholar
  • 5g Fujimoto T. Endo K. Tsuji H. Nakamura M. Nakamura E. J. Am. Chem. Soc.  2008,  130:  4492 
    Google Scholar
  • 5h Itoh Y. Tsuji H. Yamagata K.-i. Endo K. Tanaka I. Nakamura M. Nakamura E. J. Am. Chem. Soc.  2008,  130:  17161 
    Google Scholar
  • 5i Tsuji H. Tanaka I. Endo K. Yamagata K.-i. Nakamura M. Nakamura E. Org. Lett.  2009,  11:  1845 
    Google Scholar
  • 6a Tsuchimoto T. Hatanaka K. Shirakawa E. Kawakami Y. Chem. Commun.  2003,  2454 
    Google Scholar
  • 6b Mamane V. Hannen P. Fürstner A. Chem. Eur. J.  2004,  10:  4556 
    Google Scholar
  • 6c Takita R. Fukuta Y. Tsuji R. Ohshima T. Shibasaki M. Org. Lett.  2005,  7:  1363 
    Google Scholar
  • 6d Miura K. Fujisawa N. Toyohara S. Hosomi A. Synlett  2006,  1883 
    Google Scholar
  • 6e Takahashi K. Midori M. Kawano K. Ishihara J. Hatakeyama S. Angew. Chem. Int. Ed.  2008,  47:  6244 
    Google Scholar
  • 6f Nishimoto Y. Moritoh R. Yasuda M. Baba A. Angew. Chem. Int. Ed.  2009,  48:  4577 
    Google Scholar
  • 7a Feng X. Tan Z. Chen D. Shen Y. Guo C.-C. Xiang J. Zhu C. Tetrahedron Lett.  2008,  49:  4110 
    Google Scholar
  • 7b Liu X.-T. Huang L. Zheng F.-j. Zhan Z.-P. Adv. Synth. Catal.  2008,  350:  2778 
    Google Scholar
  • 7c Lin M. Hao L. Ma R.-D. Zhan Z.-P. Synlett  2010,  2345 
    Google Scholar
  • 8 FeCl3-catalyzed reaction has been also reported: Zhan Z.-P. Cai X.-B. Wang S.-P. Yu J.-L. Liu H.-J. Cui Y.-Y. J. Org. Chem.  2007,  72:  9838 
    CrossrefGoogle Scholar
  • 9 Frost CG. Hartley JP. Griffin D. Tetrahedron Lett.  2002,  43:  4789 
    CrossrefGoogle Scholar
  • For recent reviews of the synthesis and utilization of furan and pyrrole derivatives, see:
  • 10a Brown RCD. Angew. Chem. Int. Ed.  2005,  44:  850 
    Google Scholar
  • 10b Kirsch SF. Org. Biomol. Chem.  2006,  4:  2076 
    Google Scholar
  • 10c D’Souza DM. Müller TJJ. Chem. Soc. Rev.  2007,  36:  1095 
    Google Scholar
  • 10d Álvarez-Corral M. Muñoz-Dorado M. Rodríguez-García I. Chem. Rev.  2008,  108:  3174 
    Google Scholar
  • 11a Tsuji H. Mitsui C. Ilies L. Sato Y. Nakamura E. J. Am. Chem. Soc.  2007,  129:  11902 
    Google Scholar
  • 11b Tsuji H. Mitsui C. Sato Y. Nakamura E. Adv. Mater.  2009,  21:  3776 
    Google Scholar
  • 11c Tsuji H. Yokoi Y. Mitsui C. Ilies L. Sato Y. Nakamura H. Chem. Asian J.  2009,  4:  655 
    Google Scholar
  • 12 Ma S. Handbook of Cyclization Reactions   Wiley-VCH; Weinheim: 2010. 
    Google Scholar
  • 13 Imagawa H. Kurisaki T. Nishizawa M. Org. Lett.  2004,  6:  3679 
    CrossrefGoogle Scholar
  • 14 Pancote CG. de Carvalho BS. Luchez CV. Fernandes JPS. Politi MJ. Brandt CA. Synthesis  2009,  3963 
    Artikel in Thieme ConnectGoogle Scholar