General and chemoselective bisphosphonylation of secondary and tertiary amides

Organic Letters

Volumn 17, Issue 3, 2015, Pages 732-735

  Wang, Ai E ^a   Chang, Zong ^a   Sun, Wei Ting ^a   Huang, Pei Qiang ^a,b  

^a XIAMEN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMIDE; FURAN DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; SULFONAMIDE; TRIFLIC ANHYDRIDE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALDEHYDES; AMIDES; CATALYSIS; FURANS; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; SULFONAMIDES;

EID: 84922677604     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00004     Document Type: Article

References (77)

1. Martin, M. B.; Arnold, W.; Heath, H. T., III; Urbina, J. A.; Oldfield, E. Biochem. Biophys. Res. Commun. 1999, 263, 754
2. Szabo, C. M.; Martin, M. B.; Oldfield, E. J. Med. Chem. 2002, 45, 2894
3. Mao, J.; Mukherjee, S.; Zhang, Y.; Cao, R.; Sanders, J. M.; Song, Y.; Zhang, Y.; Meints, G. A.; Gao, Y. G.; Mukkamala, D.; Hudock, M. P.; Oldfield, E. J. Am. Chem. Soc. 2006, 128, 14485
4. Sietsema, W. K.; Ebetino, F. H.; Salvagno, A. M.; Bevan, J. A. Drugs Exp. Clin. Res. 1989, 15, 389
5. Yajima, S.; Hara, K.; Sanders, J. M.; Yin, F.; Ohsawa, K.; Wiesner, J.; Jomaa, H.; Oldfield, E. J. Am. Chem. Soc. 2004, 126, 10824
6. Sanders, J. M.; Gómez, A. O.; Mao, J.; Meints, G. A.; Van Brussel, E. M.; Burzynska, A.; Kafarski, P.; González-Pacanowska, D.; Oldfield, E. J. Med. Chem. 2003, 46, 5171
7. Ghosh, S.; Chan, J. M. W.; Lea, C. R.; Meints, G. A.; Lewis, J. C.; Tovian, Z. S.; Flessner, R. M.; Loftus, T. C.; Bruchhaus, I.; Kendrick, H.; Croft, S. L.; Kemp, R. G.; Kobayashi, S.; Nozaki, T.; Oldfield, E. J. Med. Chem. 2004, 47, 175
8. Kotsikorou, E.; Song, Y.; Chan, J. M. W.; Faelens, S.; Tovian, Z.; Broderick, E.; Bakalara, N.; Docampo, R.; Oldfield, E. J. Med. Chem. 2005, 48, 6128
9. Leon, A.; Liu, L.; Yang, Y.; Hudock, M. P.; Hall, P.; Yin, F.; Studer, D.; Puan, K.-J.; Morita, C. T.; Oldfield, E. J. Med. Chem. 2006, 49, 7331
10. Kafarski, P.; Lejczak, B.; Forlani, G.; Chuiko, A.; Lozinsky, M.; Jasicka-Misiak, I.; Czekaa, K.; Lipok, J. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144, 621
11. Kafarski, P.; Lejczak, B.; Forlani, G. Heteroatom Chem. 2000, 11, 449
12. Russell, R. G. G.; Croucher, P. I.; Rogers, M. J. Osteoporosis Int. 1999, Suppl. 2) 66
13. Russell, R. G. G. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144, 793
14. Widler, L.; Jaeggi, K. A.; Glatt, M.; Müller, K.; Bachmann, R.; Bisping, M.; Born, A.-R.; Cortesi, R.; Guiglia, G.; Jeker, H.; Klein, R.; Ramseier, U.; Schmid, J.; Schreiber, G.; Seltenmeyer, Y.; Green, J. R. J. Med. Chem. 2002, 45, 3721
15. Zhang, S.; Gangal, G.; Uludaʇ, H. Chem. Soc. Rev. 2007, 36, 507
16. Reszka, A. A.; Rodan, G. A. Mini Rev. Med. Chem. 2004, 4, 711
17. Uludag, H. Curr. Pharm. Design 2002, 8, 1929
18. Adler, P.; Fadel, A.; Rabasso, N. Tetrahedron 2014, 70, 4437
19. For a recent review on the synthesis of α-amino bisphosphonates see: Romanenko, V. D.; Kukhar, V. P. ARKIVOC 2012, iv, 127
20. Plöger, W.; Schindler, N.; Wollmann, K.; Worms, K. H. Z. Anorg. Allg. Chem. 1972, 389, 119
21. Fukuda, M.; Okamoto, Y.; Sakurai, H. Bull. Chem. Soc. Jpn. 1975, 48, 1030
22. Worms, K.-H.; Blum, H. Liebigs Ann. Chem. 1982, 275
23. Alferiev, I. S.; Bobkov, S. Y. Z. Naturforsch. 1992, 47b, 1213
24. Griffiths, D. V.; Hughes, J. M.; Brown, J. W.; Caesar, J. C.; Swetnam, S. P.; Cumming, S. A.; Kelly, J. D. Tetrahedron 1997, 53, 17815
25. Wu, M.; Chen, R.; Huang, Y. Synth. Commun. 2004, 34, 1393
26. Gross, H.; Costisella, B.; Gnauk, T.; Brennecke, L. J. Prakt. Chem. 1976, 318, 116
27. Qian, D. Q.; Shi, X. D.; Zeng, X. Z.; Cao, R. Z.; Liu, L. Z. Tetrahedron Lett. 1997, 38, 6245
28. Qian, D.; Zeng, X.; Shi, X.; Cao, R.; Liu, L. Heteroatom Chem. 1997, 8, 517
29. Olive, G.; Le Moigne, F.; Mercier, A.; Rockenbauer, A.; Tordo, P. J. Org. Chem. 1998, 63, 9095
30. Qian, D. Q.; Shi, X. D.; Cao, R. Z.; Liu, L. Z. Heteroatom Chem. 1999, 10, 271
31. Olive, G.; Le Moigne, F.; Mercier, A.; Tordo, P. Synth. Commun. 2000, 30, 619
32. Olive, G.; Jacques, A. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 33
33. Yu, C.-M.; Wang, B.; Chen, Z.-W. Chin. J. Chem. 2008, 26, 1899
34. Bandurina, T. A.; Konyukhov, V. N.; Ponomareva, O. A.; Barybin, A. S.; Pushkareva, Z. V. Pharm. Chem. J. 1978, 12, 1428
35. Goldeman, W.; Kluczyński, A.; Soroka, M. Tetrahedron Lett. 2012, 53, 5290
36. Masschelein, K. G. R.; Stevens, C. V. J. Org. Chem. 2007, 72, 9248
37. Maier, L. Phosphorus, Sulfur Silicon Relat. Elem. 1981, 11, 311
38. Kaboudin, B.; Alipour, S. Tetrahedron Lett. 2009, 50, 4243
39. Dabrowska, E.; Burzyńska, A.; Mucha, A.; Matczak-Jon, E.; Sawka-Dobrowolska, W.; Berlicki, A.; Kafarski, P. J. Organomet. Chem. 2009, 694, 3806
40. Yokomatsu, T.; Yoshida, Y.; Nakabayashi, N.; Shibuya, S. J. Org. Chem. 1994, 59, 7562
41. Wu, M.; Chen, R.; Huang, Y. Synthesis 2004, 2441
42. Abdou, W. M.; Shaddy, A. A. ARKIVOC 2009, ix, 143
43. Breuer, E. The Development of Bisphosphonates as Drugs. In Analogue-based Drug Discovery; Wiley-VCH: Weinheim, 2006; pp 371-384.
44. Pace, V.; Holzer, W. Aust. J. Chem. 2013, 66, 507
45. Pace, V.; Holzer, W.; Olofsson, B. Adv. Synth. Catal. 2014, 356, 3697
46. Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N. Angew. Chem., Int. Ed. 2010, 49, 6369
47. Vincent, G.; Guillot, R.; Kouklovsky, C. Angew. Chem., Int. Ed. 2011, 50, 1350
48. Yanagita, Y.; Nakamura, H.; Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N. Chem.-Eur. J. 2013, 19, 678
49. Vincent, G.; Karila, D.; Khalil, G.; Sancibrao, P.; Gori, D.; Kouklovsky, C. Chem.-Eur. J. 2013, 19, 9358
50. Jäkel, M.; Qu, J.-P.; Schnitzer, T.; Helmchen, G. Chem.-Eur. J. 2013, 19, 16746
51. Yoritate, M.; Meguro, T.; Matsuo, N.; Shirokane, K.; Sato, T.; Chida, N. Chem.-Eur. J. 2014, 20, 8210
52. Sato, T.; Chida, N. Org. Biomol. Chem. 2014, 12, 3147
53. Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485
54. Xia, Q.; Ganem, B. Tetrahedron Lett. 2002, 43, 1597
55. Oda, Y.; Sato, T.; Chida, N. Org. Lett. 2012, 14, 950
56. Shirokane, K.; Wada, T.; Yoritate, M.; Minamikawa, R.; Takayama, N.; Sato, T.; Chida, N. Angew. Chem., Int. Ed. 2014, 53, 512
57. Nakajima, M.; Oda, Y.; Wada, T.; Minamikawa, R.; Shirokane, K.; Sato, T.; Chida, N. Chem.-Eur. J. 2014, 20, 17565
58. Gao, Y.; Huang, Z.; Zhuang, R.; Xu, J.; Zhang, P.; Tang, G.; Zhao, Y. Org. Lett. 2013, 15, 4214
59. For recent reviews, see: Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077 and ref 20
60. Valerio, V.; Petkova, D.; Madelaine, C.; Maulide, N. Chem.-Eur. J. 2013, 19, 2606
61. Medley, J. W.; Movassaghi, M. Org. Lett. 2013, 15, 3614
62. Pace, V.; Castoldi, L.; Holzer, W. Chem. Commun. 2013, 49, 8383
63. Peng, B.; Geerdink, D.; Maulide, N. J. Am. Chem. Soc. 2013, 135, 14968
64. Peng, B.; Geerdink, D.; Farès, C.; Maulide, N. Angew. Chem., Int. Ed. 2014, 53, 5462
65. Pace, V.; Castoldi, L.; Mamuye, A. D.; Holzer, W. Synthesis 2014, 46, 2897
66. Peng, B.; Huang, X.; Xie, L.-G.; Maulide, N. Angew. Chem., Int. Ed. 2014, 53, 8718
67. Mewald, M.; Medley, J. W.; Movassaghi, M. Angew. Chem., Int. Ed. 2014, 53, 11634
68. Xiao, K.-J.; Luo, J.-M.; Ye, K.-Y.; Wang, Y.; Huang, P.-Q. Angew. Chem., Int. Ed. 2010, 49, 3037
69. Huo, H.-H.; Zhang, H.-K.; Xia, X.-E.; Huang, P.-Q. Org. Lett. 2012, 14, 4834
70. Huang, S.-Y.; Chang, Z.; Tuo, S.-C.; Gao, L.-H.; Wang, A.-E; Huang, P.-Q. Chem. Commun. 2013, 49, 7088
71. Xiao, K.-J.; Luo, J.-M.; Xia, X.-E.; Wang, Y.; Huang, P.-Q. Chem.-Eur. J. 2013, 19, 13075
72. Xiao, K.-J.; Wang, Y.; Huang, Y.-H.; Wang, X.-G.; Huang, P.-Q. J. Org. Chem. 2013, 78, 8305
73. Xiao, K.-J.; Wang, A.-E; Huang, Y.-H.; Huang, P.-Q. Asian J. Org. Chem. 2012, 1, 130
74. Xiao, K.-J.; Huang, Y.-H.; Huang, P.-Q. Acta Chim. Sin. 2012, 70, 1917
75. Xiao, K.-J.; Wang, A.-E; Huang, P.-Q. Angew. Chem., Int. Ed. 2012, 51, 8314
76. Takeuchi, M. Chem. Pharm. Bull. 1993, 41, 688
77. Hiraga, T.; Tanaka, S.; Yamamoto, M.; Nakagima, T.; Ozawa, H. Bone 1996, 18, 1