Simple, efficient and one-pot method for synthesis of aminomethylene gem-diphosphonic acid derivatives from ketones via Beckmann rearrangement

Synthesis

Volumn , Issue 15, 2004, Pages 2441-2444

  Wu, Mingshu ^a   Chen, Ruyu ^a   Huang, You ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Aminomethylene gem diphosphonic acid derivatives; Beckmann rearrangement; Hydroxylamine hydrochloride; Ketones; Phosphorus trichloride

Indexed keywords

KETONES; PHOSPHORUS; WATER;

GEM-DIPHOSPHONIC ACID DERIVATIVES; ONE-POT REACTION;

ORGANIC ACIDS;

AMINOMETHYLENEDIPHOSPHONIC ACID DERIVATIVE; BISPHOSPHONIC ACID DERIVATIVE; HYDROXYLAMINE; KETONE; MEDRONIC ACID; OXIME; PHOSPHORUS ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; PHOSPHORUS TRICHLORIDE; PYRIDINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; BECKMANN REARRANGEMENT; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CRYSTALLIZATION; PHOSPHORYLATION; PRECIPITATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 7644221540     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831233     Document Type: Article

References (23)

1. Fleisch, H.; Russell, R. G.; Francis, M. D. Science 1969, 165, 1262.
2. Fleisch, H. In Handbook of Experimental Pharmacology; Mundy, G. R.; Martin, T. J., Eds.; Springer-Verlag: Berlin, Heidelberg, 1993.
3. (a) Esswein, A.; Bauss, F.; Reiff, K.; Bosies, E. Bone 1995, 17, 597.
4. (b) Page, P. C. B.; Mckenzie, M. J.; Gallagher, J. A. J. Org. Chem. 2001, 66, 3704.
5. (c) Han, Y.; Young, R. N.; Gil, L.; Ruel, R. US Pat., US 6121253, 2000; Chem. Abstr. 2000, 133, 237750.
6. (d) Fleisch, H. In Handbook of Experimental Pharmacology, Vol. 83; Baker, P. F., Ed.; Springer-Verlag: Berlin, Heidelberg, 1988.
7. (a) Sietsema, W. K.; Ebetino, F. H.; Salvagno, A. M.; Bevan, J. A. Drugs Exptl. Clin. Res. 1989, XV, 389.
8. th Symposium on Medicinal Chemistry; Shizuoka: Japan, 1993, 37.
9. (a) Rodan, G. A.; Martin, T. J. Science 2000, 289, 1508.
10. (b) Shinoda, H. Bone 1999, 13, 31.
11. (c) Diel, I. J.; Mundy, G. R. Br. J. Cancer 2000, 82, 1381.
12. (a) Bamber, M.; Woodcoard, C. Eur. Pat. Appl., EP 657462, 1995; Chem. Abstr. 1995, 123, 228518.
13. (b) Gaffar, A.; Affihtlo, J. J.; Polefka, T. G.; Nabi, N.; Joziak, M. T. US Pat., US 6214320, 2001; Chem. Abstr. 2001, 134, 271079.
14. (c) Alferev, I. S.; Alferleva, L. P.; Glyadinskaya, S. A.; Kotlyarevskii, I. L.; Krasnvkhina, A. V.; Mikhalin, N. V. Izobreteniya 1998, 5, 510.
15. (d) Blum, H.; Memmann, S. Eur. Pat. Appl., EP 332068, 1989; Chem. Abstr. 1990, 112, 77540.
16. (e) Ploger, W.; Schmit-Dunker, M.; Gloxhuber, C. Ger. Pat., DE 2343196, 1975; Chem. Abstr. 1975, 83, 28371.
17. (f) Zilch, H.; Esswein, A.; Bauss, F. Ger. Patent, DE 4114586A, 1992; Chem. Abstr. 1993, 118, 80827.
18. (g) Ploger, W.; Schmit-Dunker, M.; Gloxhuber, C. Ger. Pat., DE 2343147, 1975; Chem. Abstr. 1975, 83, 28370.
19. (a) Takeuchi, M.; Sakamoto, S.; Yoshida, M.; Abe, T.; Isomura, Y. Chem. Pharm. Bull. 1993, 41, 688.
20. (b) Soloducho, J.; Gancar, R.; Wieczorek, P.; Korf, I.; Hafner, J.; Lefczak, B.; Kafarshi, P. Pol. Pat., PL 172268, 1997; Chem. Abstr. 1998, 128, 61631.
21. Yokomatsu, T.; Yoshida, Y.; Nakabayashi, N.; Shibuya, S. J. Org. Chem. 1994, 59, 7562.
22. (a) Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumuna, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831.
23. (b) Matsumura, Y.; Fujiwara, J.; Maruaka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 6312.