Synthesis of N-unsubstituted β-lactams from N-alkoxyphenyl-β- lactams with cobalt(III) fluoride

Tetrahedron Letters

Volumn 51, Issue 44, 2010, Pages 5791-5794

  Zarei, Maaroof ^a   Jarrahpour, Aliasghar ^b  

^a UNIVERSITY OF HORMOZGAN   (Iran)

^b SHIRAZ UNIVERSITY   (Iran)

Author keywords

2 Azetidinone; Cobalt(III) fluoride; N unsubstituted lactam; Oxidative N dearylation

Indexed keywords

2 AZETIDINONE DERIVATIVE; BETA LACTAM DERIVATIVE; COBALT COMPLEX; PHENYL GROUP; REAGENT; SOLVENT;

ARTICLE; ARYLATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; SPECTROSCOPY; TEMPERATURE DEPENDENCE;

EID: 77957587416     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.101     Document Type: Article

References (65)

1. T.E. Long, and E. Turos Curr. Med. Chem.-Anti-Infective Agents 1 2002 251 268
2. R. Southgate Contemp. Org. Synth. 1 1994 417 432
3. R.B. Morin, and M. Gorman Chemistry and Biology of β-Lactam Antibiotics 1982 Academic Press New York
4. N. De Kimpe A.R. Katrizky, C.W. Rees, E.F.V. Scriven, A. Padwa, Comprehensive Heterocyclic Chemistry II Vol. 1B 1996 Pergamon Oxford 507
5. G.A. Koppel A. Hasner, Small Ring Heterocycles Vol. 42 1983 Wiley New York 219
6. M. O'Driscoll, K. Greenhalgh, A. Young, E. Turos, S. Dickey, and D.V. Lim Bioorg. Med. Chem. 16 2008 7832 7837
7. X. Xu, R. Fu, J. Chen, S. Chen, and S. Bai Bioorg. Med. Chem. Lett. 17 2007 101 104
8. G. Gerona-Navarro, J.P. de Vega, M.T. Garcia-Lopez, G. Andrei, R. Snoeck, J. Balzarini, E. De Clercq, and R. Gonzalez-Muniz Bioorg. Med. Chem. Lett. 14 2004 2253 2256
9. J. Marchand-Brynaert, G. Dive, M. Galleni, and S. Gerard Bioorg. Med. Chem. 12 2004 129 138
10. J.C. Sutton, S.A. Bolton, K.S. Harti, M.H. Huang, G. Jacobs, W. Meng, G. Zhao, and G.S. Bisacchi Bioorg. Med. Chem. Lett. 14 2004 2233 2239
11. J. Tozser, T. Sperka, J. Pitlik, and P. Bagossi Bioorg. Med. Chem. Lett. 15 2005 3086 3090
12. E.L. Setti, D. Davis, J.M. Janc, D.A. Jeffery, H. Cheung, and W. Yu Bioorg. Med. Chem. Lett. 15 2005 1529 1534
13. B.K. Banik, I. Banik, and F.F. Becker Bioorg. Med. Chem. 13 2005 3611 3622
14. M. Nivsarkar, D. Thavaselvam, S. Prasanna, M. Sharma, and M.P. Kaushik Bioorg. Med. Chem. Lett. 15 2005 1371 1373
15. G. Zoidis, C. Fytas, I. Papanastasiou, G.B. Foscolos, G. Fytas, E. Padalko, E. De Clercq, L. Naesens, J. Neyts, and N. Kolocouris Bioorg. Med. Chem. 14 2006 3341 3348
16. R.K. Goel, M.P. Mahajan, and S.K. Kulkarni J. Pharm. Pharm. Sci. 7 2004 80 83
17. R.K. Goel, A. Singh, P.S. Naidu, M.P. Mahajan, and S.K. Kulkarni J. Pharm. Pharm. Sci. 8 2005 182 189
18. L.R. Domingo, M.J. Aurell, and M. Arno Tetrahedron 65 2009 3432 3440
19. B. Alcaide, P. Almendros, R. Carrascosa, and T.M. Campo Chem. Eur. J. 15 2009 2496 2499
20. E. Leemans, M. D'hooghe, Y. Dejaegher, K.W. Tornroos, and N. De Kimpe J. Org. Chem. 73 2008 1422 1428
21. R.K. Mishra, C.M. Coates, K.D. Revell, and E. Turos Org. Lett. 9 2007 575 578
22. A.A. Taubinger, D. Fenske, and J. Podlech Synlett 2008 539 542
23. B. Alcaide, P. Almendros, G. Cabrero, and M.P. Ruiza Synthesis 2008 2835 2839
24. B. Alcaide, P. Almendros, and M.C. Redondo Eur. J. Org. Chem. 2007 3707 3710
25. For a review, see: I. Ojima A. Hassner, Advances in Asymmetric Synthesis Vol. 1 1995 Jai Press Greenwich 95
26. B. Alcaide, P. Almendros, and C. Aragoncillo Chem. Rev. 107 2007 4437 4492
27. A.R.A.S. Deshmukh, B.M. Bhawal, D. Krishnaswamy, V.V. Govande, B.A. Shinkre, and A. Jayanthi Curr. Med. Chem. 11 2004 1889 1920
28. B. Alcaide, and P. Almendros Curr. Med. Chem. 11 2004 1921 1949
29. B. Alcaide, and P. Almendros Synlett 2002 381 393
30. C. Palomo, J.M. Aizpurua, I. Ganboa, and M. Oiarbide Synlett 2001 1813 1826
31. I. Ojima, and F. Delaloge Chem. Soc. Rev. 26 1997 377 386
32. A.B. Zambron, M. Masnyk, B. Furman, and M. Chmielewski Tetrahedron 65 2009 4440 4446
33. P.G. Sammes, Topics in Antibiotic Chemistry Vol. 3 1980 Ellis Horwood Ltd London
34. J. O'Sullivan, and E.P. Abraham Antibiotics Vol. 4 1981 Springer Berlin
35. G. Lukacs, M. Ohno, Recent Progress in the Chemical Synthesis of Antibiotics 1990 Springer Berlin
36. G.I. Georg, Organic Chemistry of β-Lactams 1993 VCH New York
37. M.I. Page The Chemistry of β-Lactams 1992 Chapman and Hall London
38. F.P. Cossio, B. Lecea, and C. Palomo J. Chem. Soc., Chem. Commun. 1987 1743 1744
39. M. Hodge, Q.-H. Chen, S. Bane, S. Sharma, M. Loew, A. Banerjee, A.A. Alcaraz, J.P. Snyder, and D.G.I. Kingston Bioorg. Med. Chem. Lett. 19 2009 2884 2887
40. M. Suffness Taxol Science and Applications 1995 CRC Press Boca Raton, FL
41. E. Bandini, G. Favi, G. Martelli, M. Panunzio, and G. Piersanti Org. Lett. 2 2009 1077 1079
42. A. Jarrahpour, and M. Zarei Molecules 12 2007 2364 2379
43. E. Turos, B. Heldreth, T.E. Long, S. Jang, G.S.K. Reddy, S. Dickey, and D.V. Lim Bioorg. Med. Chem. 14 2006 3775 3784
44. J. Podlech, and M.R. Linder J. Org. Chem. 62 1997 5873 5883
45. X.-G. Li, and L.T. Kanerva Adv. Synth. Catal. 348 2006 197 205
46. T.W. Green, and P.G.M. Wuts Green's Protective Groups in Organic Synthesis 4th ed. 2007 John Wiley & Sons New Jersey p 903
47. P. Del Buttero, G. Moltenia, and T. Pilati Tetrahedron 61 2005 2413 2419
48. Y. Gimbert, A.E. Greene, C. Lucatelli, and F. Viton J. Org. Chem. 67 2002 9468 9470
49. T. Fukuyama, R.K. Frank, and C.F. Jewell J. Am. Chem. Soc. 102 1980 2122 2123
50. P. Jacob, P.S. Callerv, A.T. Shulain, and N. Castaanoli J. Org. Chem. 41 1976 3627 3629
51. S. Balasubramanian, and K.H. Gordon Org. Lett. 3 2001 53 56
52. E.G. Corley, S. Karady, and N.L. Abramson Tetrahedron Lett. 29 1988 1497 1500
53. J.D. Debad, J.C. Morris, V. Lynch, P. Magnus, and A.J. Bard J. Am. Chem. Soc. 118 1996 2374 2379
54. J.D. Debad, J.C. Morris, P. Magnus, and A.J. Bard J. Org. Chem. 62 1997 530 537
55. A. Tomatsu, S. Takemura, K. Hashimoto, and M. Nakata Synlett 1999 1474 1476
56. D.R. Lide CRC Handbook of Chemistry and Physics 87th ed. 2006-2007 CRC Press Boca Raton, FL section 8, pp 20-29
57. 8ClNO: C, 59.52; H, 4.44; N, 7.71. Found: C, 59.60; H, 4.62; N, 7.65.
58. Characterization data for all compounds have been reported previously, except for 2j-k. A. Jarrahpour, M. Motamedifar, M. Zarei, and M. Mimouni Phosphorus Sulfur Silicon 185 2010 287 297
59. A. Jarrahpour, and M. Zarei Tetrahedron 65 2009 2927 2934
60. A. Jarrahpour, and M. Zarei Tetrahedron Lett. 48 2007 8712 8714
61. A. Jarrahpour, and M. Zarei Molecules 11 2006 49 58
62. A. Jarrahpour, and M. Zarei Tetrahedron Lett. 50 2009 1568 1570
63. A. Jarrahpour, and M. Zarei Synlett 2008 381
64. A. Jarrahpour, and M. Zarei Synth. Commun. 38 2008 1837 1845
65. A. Jarrahpour, and M. Zarei Phosphorus Sulfur Silicon 184 2009 1738 1749