Synthesis and cycloaddition chemistry of oxetanyl-substituted sydnones

Tetrahedron Letters

Volumn 54, Issue 24, 2013, Pages 3094-3096

  Nassoy, Anne Chloé ^a   Raubo, Piotr ^b   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Cycloadditions; Oxetanes; Pyrazoles; Regioselectivity; Sydnones

Indexed keywords

OXETAN 3 ONE; OXETANE DERIVATIVE; SYDNONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLOADDITION;

EID: 84877711637     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.03.139     Document Type: Article

References (30)

1. G. Wuitschik, M. Rogers-Evans, K. Müller, H. Fischer, B. Wagner, F. Schuler, L. Polonchuk, and E.M. Carreira Angew. Chem. Int. Ed. 45 2006 7736
2. G. Wuitschik, M. Rogers-Evans, A. Buckl, M. Bernasconi, M. Marki, T. Godel, H. Fischer, B. Wagner, I. Parrilla, F. Schuler, J. Schneider, A. Alker, W.B. Schweizer, K. Müller, and E.M. Carreira Angew. Chem. Int. Ed. 47 2008 4512
3. G. Wuitschik, E.M. Carreira, B. Wagner, H. Fischer, I. Parrilla, F. Schuler, M. Rogers-Evans, and K. Müller J. Med. Chem. 53 2010 3227
4. J.A. Burkhard, G. Wuitschik, M. Rogers-Evans, K. Müller, and E.M. Carreira Angew. Chem. Int. Ed. 49 2010 9052
5. C. Guérot, B.H. Tchitchanov, H. Knust, and E.M. Carreira Org. Lett. 13 2011 780
6. M.A.J. Duncton, M.A. Estiarte, D. Tan, C. Kaub, D.J.R. O'Mahony, R.J. Johnson, M. Cox, W.T. Edwards, M. Wan, J. Kincaid, and M.G. Kelly Org. Lett. 10 2008 3259
7. J.E. Moore, K.M. Goodenough, D. Spinks, and J.P.A. Harrity Synlett 2002 2071
8. J.E. Moore, M.W. Davies, K.M. Goodenough, R.A.J. Wybrow, M. York, C.N. Johnson, and J.P.A. Harrity Tetrahedron 61 2005 6707
9. M.D. Helm, J.E. Moore, A. Plant, and J.P.A. Harrity Angew. Chem. Int. Ed. 44 2005 3889
10. J.E. Moore, M. York, and J.P.A. Harrity Synlett 2005 860
11. P.M. Delaney, J.E. Moore, and J.P.A. Harrity Chem. Commun. 2006 3323
12. E. Gomez-Bengoa, M.D. Helm, A. Plant, and J.P.A. Harrity J. Am. Chem. Soc. 129 2007 2691
13. P.M. Delaney, D.L. Browne, H. Adams, A. Plant, and J.P.A. Harrity Tetrahedron 64 2008 866
14. A.-L. Auvinet, J.P.A. Harrity, and G. Hilt J. Org. Chem. 75 2010 3893
15. A.-L. Auvinet, and J.P.A. Harrity Angew. Chem. Int. Ed. 50 2011 2769
16. F.H.C. Stewart Chem. Rev. 64 1964 129
17. D.L. Browne, and J.P.A. Harrity Tetrahedron 66 2010 553
18. D.L. Browne, M.D. Helm, A. Plant, and J.P.A. Harrity Angew. Chem. Int. Ed. 46 2007 8656
19. D.L. Browne, J.F. Vivat, A. Plant, E. Gomez-Bengoa, and J.P.A. Harrity J. Am. Chem. Soc. 131 2009 7762
20. R.S. Foster, J. Huang, J.F. Vivat, D.L. Browne, and J.P.A. Harrity Org. Biomol. Chem. 7 2009 4052
21. D.L. Browne, J.B. Taylor, A. Plant, and J.P.A. Harrity J. Org. Chem. 74 2009 396
22. D.L. Browne, J.B. Taylor, A. Plant, and J.P.A. Harrity J. Org. Chem. 75 2010 984
23. H.-J. Tien, G.-M. Fang, S.-T. Lin, and L.-L. Tien J. Chin. Chem. Soc. 39 1992 107
24. R. Huisgen, R. Grashley, H. Gotthardt, and R. Schmidt Angew. Chem. Int. Ed. 1 1962 48
25. C. Wu, Y. Fang, R.C. Larock, and F. Shi Org. Lett. 12 2010 2234
26. T. Delauney, P. Geux, M. Es-Sayed, J.-P. Vors, N. Monteiro, and G. Balme Org. Lett. 12 2010 3328
27. Y. Fang, C. Wu, R.C. Larock, and F. Shi J. Org. Chem. 76 2011 8840
28. A. Padwa, E.M. Burgess, H.L. Gingrich, and D.M. Roush J. Org. Chem. 47 1982 786
29. The low molecular weight and lipophilicity of compound 16 offers the opportunity to incorporate a range of fragments for lead discovery (estimated clog P = -1.3; ChemBioDraw Ultra™ version 12.0 A. Nadin, C. Hattotuwagama, and I. Churcher Angew. Chem. Int. Ed. 51 2012 1114
30. R.S. Foster, H. Jakobi, and J.P.A. Harrity Org. Lett. 14 2012 4858