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Synthesis 2009(14): 2454-2466  
DOI: 10.1055/s-0029-1216867
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Syntheses of Substituted Furans and Pyrroles by Platinum-Catalyzed Cyclizations of Propargylic Oxiranes and Aziridines in Aqueous Media

Masahiro Yoshida*, Mohammad Al-Amin, Kozo Shishido
Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan
Fax: +81(88)6337294; e-Mail: yoshida@ph.tokushima-u.ac.jp;
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Publication History

Received 11 May 2009
Publication Date:
26 June 2009 (online)

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Abstract

The reactions of propargylic oxiranes and aziridines with a platinum catalyst in aqueous media are described. Furans having a variety of substituents were conveniently synthesized by the platinum-catalyzed reaction of propargylic oxiranes. The reaction in the presence of N-iodosuccinimide afforded the 3-iodo-substituted furan, which was further functionalized to tetrasubstituted furans with high efficiency. Propargylic aziridines were also reacted with the platinum catalyst to produce the corresponding substituted pyrroles in good yields.

Key words

alkyne - epoxide - furan - platinum - pyrrole

    References

  • 1a Keay BA. Dibble PW. In Comprehensive Heterocyclic Chemistry   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996.  p.395 
    Google Scholar
  • 1b Piozzi F. Bruno M. Rosselli S. Maggio A. Heterocycles  2007,  74:  31 
    Google Scholar
  • 1c Fan H. Peng J. Hamann MT. Hu J.-F. Chem. Rev.  2008,  108:  264 
    Google Scholar
  • 1d Bellina F. Rossi R. Tetrahedron  2006,  62:  7213 
    Google Scholar
  • 2a Patterson JM. Synthesis  1976,  281 
    Google Scholar
  • 2b Lipshutz BH. Chem. Rev.  1986,  86:  795 
    Google Scholar
  • 2c Tsubuki M. J. Synth. Org. Chem., Jpn.  1993,  51:  399 
    Google Scholar
  • 2d Piancatelly G. D’Auria M. D’Onofrio F. Synthesis  1994,  867 
    Google Scholar
  • 2e Wong HNC. Pure Appl. Chem.  1996,  68:  335 
    Google Scholar
  • 2f Kappe CO. Murphree SS. Padwa A. Tetrahedron  1997,  53:  14179 
    Google Scholar
  • 2g Ciufolini MA. Hermann CYW. Dong Q. Shimizu T. Swaminathan S. Xi N. Synlett  1998,  105 
    Google Scholar
  • 2h Schroeter S. Stock C. Bach T. Tetrahedron  2005,  61:  2245 
    Google Scholar
  • 3a Trofimov BA. Mikhaleva AI. Heterocycles  1994,  37:  1193 
    Google Scholar
  • 3b Hou XL. Cheung HY. Hon TY. Kwan PL. Lo TH. Tong SY. Wong HNC. Tetrahedron  1998,  54:  1955 
    Google Scholar
  • 3c Kirsch SF. Org. Biomol. Chem.  2006,  4:  2076 
    Google Scholar
  • 3d Balme G. Bouyssi D. Monteiro N. Heterocycles  2007,  73:  87 
    Google Scholar
  • 3e Patil NT. Yamamoto Y. ARKIVOC  2007,  (x):  121 
    Google Scholar
  • 3f Schmuck C. Rupprecht D. Synthesis  2007,  3095 
    Google Scholar
  • 3g Balme G. Bouyssi D. Monteiro N. Heterocycles  2007,  73:  84 
    Google Scholar
  • 3h Ono N. Heterocycles  2008,  75:  243 
    Google Scholar
  • 4a Berbalk H. Eichinger K. Winetzhammer W. Helv. Chim. Acta  1981,  64:  1026 
    Google Scholar
  • 4b Ribereau P. Queguiner G. Can. J. Chem.  1983,  61:  334 
    Google Scholar
  • 4c Marshall JA. DuBay WJ. J. Org. Chem.  1991,  56:  1685 
    Google Scholar
  • 4d Katritzky AR. Li J. J. Org. Chem.  1995,  60:  638 
    Google Scholar
  • 4e McDonald FE. Schultz CC. J. Am. Chem. Soc.  1994,  116:  9363 
    Google Scholar
  • 4f Aurrecoechea JM. Pérez E. Solay M. J. Org. Chem.  2001,  66:  564 
    Google Scholar
  • 4g Lo C.-Y. Guo H. Lian J.-J. Shen F.-M. Liu R.-S. J. Org. Chem.  2002,  67:  3930 
    Google Scholar
  • 4h Hashmi ASK. Sinha P. Adv. Synth. Catal.  2004,  346:  432 
    Google Scholar
  • 4i Blanc A. Tenbrink K. Weibel J.-M. Pale P. J. Org. Chem.  2009,  74:  4360 
    Google Scholar
  • 5a Yoshida M. Ueda H. Ihara M. Tetrahedron Lett.  2005,  46:  6705 
    Google Scholar
  • 5b Yoshida M. Morishita Y. Ihara M. Tetrahedron Lett.  2005,  46:  3669 
    Google Scholar
  • 5c Yoshida M. Hayashi M. Shishido K. Org. Lett.  2007,  9:  1643 
    Google Scholar
  • 5d Yoshida M. Hayashi M. Matsuda K. Shishido K. Heterocycles  2009,  77:  193 
    Google Scholar
  • 6a Zhang L. Sun J. Kozmin SA. Adv. Synth. Catal.  2006,  348:  2271 
    Google Scholar
  • 6b Fürstner A. Davies PD. Angew. Chem. Int. Ed.  2007,  46:  3410 
    Google Scholar
  • 7 One part of the results on our preliminary studies has been published: Yoshida M. Al-Amin M. Matsuda K. Shishido K. Tetrahedron Lett.  2008,  49:  5021 
    CrossrefGoogle Scholar
  • 9 Enhancement of the reactivity for a gold-catalyzed reaction in water has been reported: Yao X. Li C.-J. Org. Lett.  2006,  8:  1953 
    CrossrefPubMedGoogle Scholar
  • Similar transformations using gold catalysts have been reported:
  • 10a Buzas A. Gagosz F. Org. Lett.  2006,  8:  515 
    Google Scholar
  • 10b Buzas A. Istrate F. Gagosz F. Org. Lett.  2006,  8:  1957 
    Google Scholar
  • 10c Crone B. Kirsh SF. J. Org. Chem.  2007,  72:  5435 
    Google Scholar
  • 11 Recently, Liu reported the synthesis of 3-iodofurans by electrophilic cyclization of propargylic oxiranes using iodine: Xie Y.-X. Liu XY. Wu L.-Y. Han Y. Zhao L.-B. Fan M.-J. Liang YM. Eur. J. Org. Chem.  2008,  1013 
    CrossrefGoogle Scholar
  • 12 Joullié reported the byproduction of a pyrrole when a ring-opening reaction of a propargylic aziridine using CuOAc and DBU was attempted: Forbeck EM. Evans CD. Gilleran JA. Li P. Joullié MM. J. Am. Chem. Soc.  2007,  129:  14463 
    CrossrefPubMedGoogle Scholar
  • 13 During the preparation of this manuscript, the gold-catalyzed cyclization of propargylic aziridines was reported: Davies PW. Martin N. Org. Lett.  2009,  11:  2293 
    CrossrefPubMedGoogle Scholar
  • 14 Chemla F. Ferreira F. Hebbe V. Stercklen E. Eur. J. Org. Chem.  2002,  1385 
    CrossrefGoogle Scholar
  • 15 Okuro K. Furuune M. Enna M. Miura M. Nomura M. J. Org. Chem.  1993,  58:  4716 
    Google Scholar
  • 16 Alexakis A. Marek I. Mangeney P. Normant JF. Tetrahedron  1991,  47:  1677 
    CrossrefGoogle Scholar
  • 17 Shavrin KN. Gvozdev VD. Nefedov OM. Mendeleev Commun.  1995,  5:  181 
    CrossrefGoogle Scholar
8

Hashmi also reported the conversion of 1i using a gold catalyst, in which the reaction was complete in 17 h affording 2i in 80% yield; see ref 4h.