An efficient and general synthesis of pyrroles

Tetrahedron Letters

Volumn 52, Issue 18, 2011, Pages 2320-2323

  Sharland, Christopher M ^a   Singkhonrat, Jirada ^a   Najeebullah, Muhammad ^a   Hayes, Simon J ^a   Knight, David W ^a   Dunford, Damian G ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

5 endo Dig; Heterogeneous catalyst; Pyrroles; Silver(I); Synthesis

Indexed keywords

PYRROLE DERIVATIVE; SILICA GEL; SILVER NITRATE;

ARTICLE; CATALYST; CYCLIZATION; DEHYDRATION; QUANTITATIVE ANALYSIS; SYNTHESIS;

EID: 79953276331     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.085     Document Type: Article

References (28)

1. S.J. Hayes, D.W. Knight, M.D. Menzies, M. O'Halloran, and W.-F. Tan Tetrahedron Lett. 48 2007 7709 7712
2. A.R. Battersby Proc. Royal. Soc. London., Series B-BioSci. 225 1985 1 26
3. Lipitor: E. Oldfield Acc. Chem. Res. 43 2010 1216 1226
4. C.W. Lindsley ACS Chem. Neurosci. 1 2010 407 408
5. Polypyrroles: J.X. Huang Pure Appl. Chem. 78 2006 367 376
6. J.H. Huang, and R.B. Kaner Chem. Commun. 2006 367 376
7. J. Bergman, and T. Janosik A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, R.J.K. Taylor, Comprehensive Heterocyclic Chemistry III(1995-2007) 2008 Elsevier St. Louis and Oxford vol. 3.03, pp 269-351
8. R.J. Sundberg A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II(1984-1996) 1996 Elsevier St. Louis and Oxford Vol. 2.03, pp 119-206 and references therein.
9. For an extensive listing of very recent methods of pyrrole synthesis, see: E. Merkul, C. Boersch, W. Frank, and T.J.J. Müller Org. Lett. 11 2009 2269 2272
10. For a review of multi-component pyrrole syntheses, see: V. Estevez, M. Villacampa, and J. Carlos Chem. Soc. Rev. 39 2010 4402 4421
11. D.W. Knight Prog. Heterocycl. Chem. 14 2002 19 51
12. J.J. Gridley, M.P. Coogan, D.W. Knight, K.M.A. Malik, C.M. Sharland, J. Singkhonrat, and S. Williams Chem. Commun. 2003 2550 2551
13. R. Grandel, and U. Kazmaier Eur. J. Org. Chem. 1998 1833 1840
14. B.C.J. Van Esseveldt, F.L. Van Delft, J.M.M. Smits, R. De Gelder, H.E. Schoemaker, and F.P.J.T. Rutjes Adv. Synth. Catal. 346 2004 823 834
15. B.C.J. Van Esseveldt, F.L. Van Delft, J.M.M. Smits, R. De Gelder, and F.P.J.T. Rutjes Synlett 2003 2354 2358
16. B.C.J.V. Esseveldt, P.W.H. Vervoort, F.L.V. Delft, and F.P.G.T. Rutjes J. Org. Chem. 70 2005 1791 1795
17. M. Overhand, and S.M. Hecht J. Org. Chem. 59 1994 4721 4722
18. For an Au(III)-catalysed version, see: N. Gouault, M. Le Roch, C. Cornée, M. David, and P. Uriac J. Org. Chem. 74 2009 5614 5617
19. H. Yamamoto, I. Sasaki, Y. Hirai, K. Namba, H. Imagawa, and M. Nishizawa Angew. Chem., Int. Ed. 48 2009 1244 1246
20. M. Nishizawa, H. Imagawa, and H. Yamamoto Org. Biomol. Chem. 8 2010 511 521 and references therein
21. E. Herranz, and K.B. Sharpless Org. Synth. Coll. Vol. 7 1990 375 381
22. G.M.M. El-Taeb, A.B. Evans, D.W. Knight, and S. Jones Tetrahedron Lett. 42 2001 5945 5948
23. C.M. Haskins, and D.W. Knight Tetrahedron Lett. 45 2004 599 601 and references therein.
24. We have previously observed such intermediates in copper(I)-catalysed cyclisations leading to pyrroles, see: D.W. Knight, and C.M. Sharland Synlett 2004 119 121
25. and Sharland, C. M. unpublished results, and from iodocyclisations, see: D.W. Knight, H.C. Rost, C.M. Sharland, and J. Singkhonrat Tetrahedron Lett. 48 2007 7906 7910
26. For an excellent summary of such silver-catalysed processes, see: J.-M. Weibel, A. Blanc, and P. Pale Chem. Rev. 108 2008 3149 3173
27. D. Dunford, M. Guyader, S. Jones, D.W. Knight, M.B. Hursthouse, and S.J. Coles Tetrahedron Lett. 49 2008 2240 2242
28. For an extensive overview of the use of 'coinage' metals in heterocyclic synthesis, see: N.T. Patil, and Y. Yamamoto Chem. Rev. 108 2008 3395 3442