Synthesis of γ-lactams via a domino Michael addition/cyclization reaction of vinyl selenone with substituted amides

Tetrahedron Letters

Volumn 54, Issue 49, 2013, Pages 6755-6757

  Sternativo, Silvia ^a   Battistelli, Benedetta ^a   Bagnoli, Luana ^a   Santi, Claudio ^a   Testaferri, Lorenzo ^a   Marini, Francesca ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Cyclizations; Domino reactions; Lactams; Michael additions; Vinyl selenones

Indexed keywords

GAMMA LACTAM DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; NUCLEOPHILICITY; PROCESS OPTIMIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 84886953064     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.004     Document Type: Article

References (43)

1. For selected examples see: K. Das Sarma, J. Zhang, Y. Huang, and J.G. Davidson Eur. J. Org. Chem. 2006 3730 3737
2. P.A. Reddy, B.C.H. Hsiang, T.N. Latifi, M.W. Hill, K.E. Woodward, S.M. Rothman, J.A. Ferrendelli, and D.F. Covey J. Med. Chem. 39 1996 1898 1906
3. J.J.-W. Duan, L. Chen, Z.R. Wasserman, Z. Lu, R.-Q. Liu, M.B. Covington, M. Qian, K.D. Hardman, R.L. Magolda, R.C. Newton, D.D. Christ, R.R. Wexler, and C.P. Decicco J. Med. Chem. 45 2002 4954 4957
4. W.M. Kazmierski, W. Andrews, E. Furfine, A. Spaltenstein, and L.W. Wright Bioorg. Med. Chem. Lett. 14 2004 5689 5692
5. C.H. Yoon, A. Nagle, C. Chen, D. Gandhi, and K.W. Jung Org. Lett. 5 2003 2259 2262
6. D.M. Barnes, J. Ji, M.G. Fickes, M.A. Fitzgerald, S.A. King, H.E. Morton, F.A. Plagge, M. Preskill, S.H. Wagaw, S.J. Wittenberger, and J. Zhang J. Am. Chem. Soc. 124 2002 13097 13105
7. M. Blangetti, A. Deagostino, G. Gervasio, D. Marabello, C. Prandi, and P. Venturello Org. Biomol. Chem. 9 2011 2535 2538
8. D. Yang, G.-Y. Lian, H.-F. Yang, J.-D. Yu, D.-W. Zhang, and G. Xiang J. Org. Chem. 74 2009 8610 8615
9. I. Tellitu, S. Serna, M.T. Herrero, I. Moreno, E. Domínguez, and R. SanMartin J. Org. Chem. 72 2007 1526 1529
10. C. Shu, M.-Q. Liu, S.-S. Wang, L. Li, and L.-W. Ye J. Org. Chem. 78 2013 3292 3299
11. C.-Y. Zhou, and C.-M. Che J. Am. Chem. Soc. 129 2007 5828 5829
12. X.-Y. Liu, C.-H. Li, and C.-M. Che Org. Lett. 8 2006 2707 2710
13. T.K. Hyster, K.E. Ruhl, and T. Rovis J. Am. Chem. Soc. 135 2013 5364 5367
14. C.H. Yoon, A. Nagle, C. Chen, D. Gandhi, and K.W. Jung Org Lett. 5 2003 2259 2262
15. W. Van Brabandt, and N. De Kimpe J. Org. Chem. 70 2005 3369 3374
16. W. Van Brabandt, and N. De Kimpe J. Org. Chem. 70 2005 8717 8722
17. J.-H. Park, J.-R. Ha, S.-J. Oh, J.-A. Kim, D.-S. Shin, T.-J. Won, Y.-F. Lam, and C. Ahn Tetrahedron Lett. 46 2005 1755 1757
18. For selected examples of synthesis of lactams by domino Michael initiated processes see: I. Allous, S. Comesse, M. Sanselme, and A. Daïch Eur. J. Org. Chem. 2011 5303 5310
19. M. Saber, S. Comesse, V. Dalla, A. Daich, M. Sanselme, and P. Netchitailo Synlett 2010 2197 2201
20. S. Comesse, M. Sanselme, and A. Daich J. Org. Chem. 73 2008 5566 5569
21. T.B. Poulsen, G. Dickmeiss, J. Overgaard, and K.A. Jorgensen Angew. Chem.; Int. Ed. 47 2008 4687 4690
22. M. Scansetti, X. Hu, B.P. McDermott, and H.W. Lam Org. Lett. 9 2007 2159 2162
23. L.F. Tietze, and P.L. Steck Eur. J. Org. Chem. 2001 4353 4356
24. For a reactions with vinyl sulfonium salts and malonyl amides see: C. Xie, D. Han, H. Yue, J. Liu, and T. Xie Tetrahedron Lett. 51 2010 5238 5241
25. S. Sternativo, A. Calandriello, F. Costantino, L. Testaferri, M. Tiecco, and F. Marini Angew. Chem.; Int. Ed. 50 2011 9382 9385
26. F. Marini, S. Sternativo, F. Del Verme, L. Testaferri, and M. Tiecco Adv. Synth. Catal. 351 2009 1801 1806
27. F. Marini, S. Sternativo, F. Del Verme, L. Testaferri, and M. Tiecco Adv. Synth. Catal. 351 2009 103 106
28. S. Sternativo, O. Walczak, B. Battistelli, L. Testaferri, and F. Marini Tetrahedron 68 2012 10536 10541
29. S. Sternativo, F. Marini, F. Del Verme, A. Calandriello, L. Testaferri, and M. Tiecco Tetrahedron 66 2010 6851 6857
30. L. Bagnoli, C. Scarponi, M.G. Rossi, L. Testaferri, and M. Tiecco Chem. Eur. J. 17 2011 993 999
31. L. Bagnoli, S. Casini, F. Marini, C. Santi, and L. Testaferri Tetrahedron 69 2013 481
32. B.C. MilChallis, and J.A. Challis I.O. Sutherland, Comprehensive Organic Chemistry Vol. 2 1979 Pergamon Press Oxford 976 980
33. For reviews see: R. Pradhan, M. Patra, A.K. Behera, B.K. Mishra, and R.K. Behera Tetrahedron 62 2006 779 828
34. S. Kotha, A.C. Deb, K. Lahiri, and E. Manivannan Synthesis 2 2009 165 193
35. N.R. Ball-Jones, J.J. Badillo, and A.K. Franz Org. Biomol. Chem. 10 2012 5165 5181
36. For recent synthesis of spiro lactams and spiro oxindoles see: C.L. Moody, V. Franckevicius, P. Drouhin, J.E.M.N. Klein, and R.J.K. Taylor Tetrahedron Lett. 53 2012 1897 1899
37. Z. Xu, K. Huang, T. Liu, M. Xie, and H. Zhang Chem. Commun. 2011 4923 4925
38. F.-A. Kang, and Z. Sui Tetrahedron Lett. 52 2011 4204 4206
39. J.E. Thomson, A.F. Kyle, K.B. Ling, S.R. Smith, A.M.Z. Slawin, and A.D. Smith Tetrahedron 66 2010 3801 3813
40. J.D. Hansen, B.J. Newhouse, S. Allen, A. Anderson, T. Eary, J. Schiro, J. Gaudino, E. Laird, A.C. Allen, D. Chantry, C. Eberhardt, and L.E. Burgess Tetrahedron Lett. 47 2006 69 72
41. Y. Zhao, S. Yu, W. Sun, L. Liu, J. Lu, D. McEachern, S. Shargary, D. Bernard, X. Li, T. Zhao, P. Zou, D. Sun, and S. Wang J. Med. Chem. 56 2013 5553 5561
42. S. Crosignani, P. Page, M. Missotten, V. Colovray, C. Cleva, J.-F. Arrighi, J. Atherall, J. Macritchie, T. Martin, Y. Humbert, M. Gaudet, D. Pupowicz, M. Maio, P.-A. Pittet, L. Golzio, C. Giachetti, C. Rocha, G. Bernardinelli, Y. Filinchuk, A. Scheer, M.K. Schwarz, and A. Chollet J. Med. Chem. 51 2008 2227 2243
43. A.P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schürmann, H. Preut, S. Ziegler, D. Rauh, and H. Waldmann Nat. Chem. 2 2010 735 740