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RESEARCH ARTICLE
Contents Vol 65(10)

One-Pot, Three-Step Reaction of 5-[(Trimethylsilyl)ethynyl]pyrrolidin-2-one with Azides Catalyzed by CuI: Synthesis of a Novel Class of 1,4-Disubstituted 1,2,3-Triazoles

Hélio A. Stefani A D , Fernando P. Ferreira B and Adriano S. Vieira C
+ Author Affiliations
- Author Affiliations

A Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP – Brazil – CEP 05508-900.

B Departamento de Biofísica, Universidade Federal de São Paulo, São Paulo, SP – Brazil – CEP 04023-062.

C Instituto de Química, Universidade Estadual de Campinas, Campinas, SP – Brazil – CEP 13083-866.

D Corresponding author. Email: hstefani@usp.br

Australian Journal of Chemistry 65(10) 1443-1450 https://doi.org/10.1071/CH12255
Submitted: 23 May 2012  Accepted: 26 July 2012   Published: 31 August 2012

Abstract

A very fast, easy and efficient synthesis is described for a novel and biologically important class of 1,4-disubstituted-4-(5-pyrrolidin-2-one)-1,2,3-triazoles by an ultrasound-assisted one-pot, three-step click reaction sequence of 5-[(trimethylsilyl)ethynyl]pyrrolidin-2-one with organic azides mediated by catalytic CuI salts.


References

[1]  H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXksVOis78%3D&md5=af962a1dfdc14748785758477eb28f57CAS |

[2]  W. G. Lewis, L. G. Green, F. Grynspan, Z. Radic, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless, Angew. Chem. 2002, 114, 1095.

[3]  R. Huisgen, G. Szeimies, L. Möbius, Chem. Ber. 1967, 100, 2494.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2sXkvF2gur4%3D&md5=b2b32ea1c631336aa50ae149e8bfc2aeCAS |

[4]  (a) H. C. Kolb, K. B. Sharpless, Drug Discov. Today 2003, 8, 1128.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpvVWkuro%3D&md5=6a28e42e0684a2efcca5603bbdcc059cCAS |
      (b) V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) W. H. Binder, C. Kluger, Curr. Org. Chem. 2006, 10, 1791.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2007, 28, 15.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. D. Moorhouse, J. E. Moses, ChemMedChem 2008, 3, 715.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2008, 29, 952.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) J.-F. Lutz, Z. Zarafshani, Adv. Drug Deliv. Rev. 2008, 60, 958.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) F. Friscourt, G.-J. Boons, Org. Lett. 2010, 12, 4936.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) H. Srinivas, K. Sudhir, J. Org. Chem. 2006, 71, 364.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) B. H. M. Kuijpers, S. Groothuys, A. R. KeereWeer, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. Van Delf, F. P. J. Rutjes, Org. Lett. 2004, 6, 3123.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) I. E. Valverde, A. F. Delmas, V. Aucagne, Tetrahedron 2009, 65, 7597.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  E.-H. Ryu, Y. Zhao, Org. Lett. 2005, 7, 1035.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhslGhtrw%3D&md5=64e038154102037350f47bcb9c127227CAS |

[7]  (a) P. Wu, A. K. Feldman, A. K. Nugent, C. J. Hawker, A. Scheel, B. Voit, J. Pyun, J. M. J. Frechet, K. B. Sharpless, V. V. Fokin, Angew. Chem. Int. Ed. 2004, 43, 3928.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmsFSrsLs%3D&md5=cff0ebd72cd85df78299d2f4b604449cCAS |
      (b) A. J. Scheel, H. Komber, B. I. Voit, Macromol. Rapid Commun. 2004, 25, 1175.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) M. Aufort, J. Herscovici, P. Bouhours, N. Moreau, C. Girard, Bioorg. Med. Chem. Lett. 2008, 18, 1195.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsFWksrs%3D&md5=4adf30267e063316eab53833c13a0c87CAS |
      (b) F. Pagliai, E. D. Pirali, E. D. Grosso, R. D. Brisco, G. C. Tron, G. Sorba, A. A. Genazzani, J. Med. Chem. 2006, 49, 467.
         | Crossref | GoogleScholarGoogle Scholar |

[9]     (a) D. S. Matteson, Stereodirected Synthesis with Organoboranes 1995 (Springer: Berlin).
         (b) A. Pelter, K. Smith, H. C. Brown, Borane Reagents 1988 (Academic: London).
      (c) K. L. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) D. M. Knapp, E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2009, 131, 6961.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) K. L. Billingsley, S. L. Buchwald, Angew. Chem. Int. Ed. 2008, 47, 4695.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  (a) S. Darses, J.-P. Genêt, Eur. J. Org. Chem. 2003, 2003, 4313.For reviews of organotrifluoroborate salts, see:
         | Crossref | GoogleScholarGoogle Scholar |
      (b) G. A. Molander, R. Figueroa, Aldrichim Acta 2005, 38, 49.
      (c) G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) H. A. Stefani, R. Cella, A. S. Vieira, Tetrahedron 2007, 63, 3623.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) S. Darses, J.-P. Genêt, Chem. Rev. 2008, 108, 288.
         | Crossref | GoogleScholarGoogle Scholar |

[11]     (a) N-acyliminium ion chemistry, see: H. de Koning, W. N. Speckamp, in Houben-Weyl, Stereoselective Synthesis (Houben-Weyl) 1995, Vol. E21, p. 1953 (Eds G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann) (Thieme: Stuttgart).
      (b) W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  (a) R. A. Pilli, L. C. Dias, A. O. Maldaner, J. Org. Chem. 1995, 60, 717.See, for example,
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXjtlOhtro%3D&md5=e5ce2386b8d9382d16f1e8858a6824ceCAS |
      (b) R. A. Pilli, D. Russowsky, J. Org. Chem. 1996, 61, 3187.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. Dhimane, C. Vanucci, G. Lhommet, Tetrahedron Lett. 1997, 38, 1415.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. A. Batey, D. B. Mackay, Tetrahedron Lett. 2000, 41, 9935.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. O. H. El-Nezhawy, H. I. El-Diwani, R. R. Schmidt, Eur. J. Org. Chem. 2002, 4137.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. J. Bennett, A. J. Blake, P. A. Cooke, C. R. A. Godfrey, P. L. Pickering, N. S. Simpkins, M. D. Walker, C. Wilson, Tetrahedron 2004, 60, 4491.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  (a) A. S. Vieira, F. P. Ferreira, P. F. Fiorante, R. C. Guadagnin, H. A. Stefani, Tetrahedron 2008, 64, 3306.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXis1Cmu7c%3D&md5=b0d1532b745168e81e831ecf22b695faCAS |
      (b) A. S. Vieira, P. F. Fiorante, T. L. S. Hough, F. P. Ferreira, D. S. Lüdtke, H. A. Stefani, Org. Lett. 2008, 10, 5215.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. S. Vieira, P. F. Fiorante, J. Zukerman-Schpector, D. Alves, G. V. Botteselle, H. A. Stefani, Tetrahedron 2008, 64, 7234.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. C. Guadagnin, C. A. Suganuma, F. V. Singh, A. S. Vieira, R. Cella, H. A. Stefani, Tetrahedron Lett. 2008, 49, 4713.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) G. V. Botteselle, T. L. S. Hough, R. C. Venturoso, R. Cella, A. S. Vieira, H. A. Stefani, Aust. J. Chem. 2008, 61, 870.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  H. A. Stefani, A. S. Vieira, M. F. Z. J. Amaral, L. Cooper, Tetrahedron Lett. 2011, 52, 4256.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXptVWkt7Y%3D&md5=03ac28d7c622d57884e0cd6a86a9ae95CAS |

[15]  E. Bratt, K. U. S. Granberg, US Patent 2009/0111822 A1.

[16]  S. Louwrier, M. Ostendorf, A. Bomn, H. Hiemstra, W. N. Speckamp, Tetrahedron 1996, 52, 2603.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XhtVajurk%3D&md5=b2d8f56a74223c90b37735acd2ea452bCAS |

[17]  (a) A. S. Cieplak, J. Am. Chem. Soc. 1981, 103, 4540.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3MXks1Whurc%3D&md5=48d3e6238820ab21a75e9b3f657edf4dCAS |
      (b) A. I. Meyers, R. H. Wallace, J. Org. Chem. 1989, 54, 2509.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  (a) L. O. Jeroncic, M. P. Cabal, S. J. Danishefsky, G. M. Shulte, J. Org. Chem. 1991, 56, 387.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkt1Kitg%3D%3D&md5=88e186bba5899569ec72c7557643a71fCAS |
      (b) S. J. Danishefsky, M. P. Cabal, K. Chow, J. Am. Chem. Soc. 1989, 111, 3456.
         | Crossref | GoogleScholarGoogle Scholar |