Simple, Efficient and One-Pot Method for Synthesis of Aminomethylene gem-Diphosphonic Acid Derivatives from Ketones via Beckmann Rearrangement

Abstract

A simple, expeditious and convenient synthesis of aminomethylene gem-diphosphonic acid derivatives in one-pot reaction using ketones, hydroxylamine hydrochloride, phosphorus trichloride and water as starting materials in the presence of pyridine via Beckmann rearrangement is described in the modest yields.

Key words

aminomethylene gem-diphosphonic acid derivatives - ketones - Beckmann rearrangement - hydroxylamine hydrochloride - phosphorus trichloride

References

• 1 Fleisch H. Russell RG. Francis MD. Science  1969,  165:  1262 
• 2 Fleisch H. In Handbook of Experimental Pharmacology   Mundy GR. Martin TJ. Springer-Verlag; Berlin, Heidelberg: 1993. 
• 3a Esswein A. Bauss F. Reiff K. Bosies E. Bone  1995,  17:  597 
• 3b Page PCB. Mckenzie MJ. Gallagher JA. J. Org. Chem.  2001,  66:  3704 
• 3c Han Y, Young RN, Gil L, and Ruel R. inventors; US Pat., US  6121253.  ; Chem. Abstr. 2000, 133, 237750
• 3d Fleisch H. In Handbook of Experimental Pharmacology   Vol. 83:  Baker PF. Springer-Verlag; Berlin, Heidelberg: 1988. 
• 4a Sietsema WK. Ebetino FH. Salvagno AM. Bevan JA. Drugs Exptl. Clin. Res.  1989,  XV:  389 
• 4b Oda T. Oi S. Taketomi S. Mizoguchi J. Tozawa R. Kitano K. Shoda T. 3 ^rd Annual Meeting of Division of Medicinal Chemistry and 14 ^th Symposium on Medicinal Chemistry   Shizuoka; Japan: 1993.  p.37 
• 5a Rodan GA. Martin TJ. Science  2000,  289:  1508 
• 5b Shinoda H. Bone  1999,  13:  31 
• 5c Diel IJ. Mundy GR. Br. J. Cancer  2000,  82:  1381 
• 6a Bamber M, and Woodcoard C. inventors; Eur. Pat. Appl., EP  657462.  ; Chem. Abstr. 1995, 123, 228518
• 6b Gaffar A, Affihtlo JJ, Polefka TG, Nabi N, and Joziak MT. inventors; US Pat., US  6214320.  ; Chem. Abstr. 2001, 134, 271079
• 6c Alferev IS. Alferleva LP. Glyadinskaya SA. Kotlyarevskii IL. Krasnvkhina AV. Mikhalin NV. Izobreteniya  1998,  5:  510 
• 6d Blum H, and Memmann S. inventors; Eur. Pat. Appl., EP  332068.  ; Chem. Abstr. 1990, 112, 77540
• 6e Ploger W, Schmit-Dunker M, and Gloxhuber C. inventors; Ger. Pat., DE  2343196.  ; Chem. Abstr. 1975, 83, 28371
• 6f Zilch H, Esswein A, and Bauss F. inventors; Ger. Patent, DE  4114586A.  ; Chem. Abstr. 1993, 118, 80827
• 6g Ploger W, Schmit-Dunker M, and Gloxhuber C. inventors; Ger. Pat., DE  2343147.  ; Chem. Abstr. 1975, 83, 28370
• 7a Takeuchi M. Sakamoto S. Yoshida M. Abe T. Isomura Y. Chem. Pharm. Bull.  1993,  41:  688 
• 7b Soloducho J, Gancar R, Wieczorek P, Korf I, Hafner J, Lefczak B, and Kafarshi P. inventors; Pol. Pat., PL  172268.  ; Chem. Abstr. 1998, 128, 61631
• 8 Yokomatsu T. Yoshida Y. Nakabayashi N. Shibuya S. J. Org. Chem.  1994,  59:  7562 
• 9a Maruoka K. Miyazaki T. Ando M. Matsumuna Y. Sakane S. Hattori K. Yamamoto H. J. Am. Chem. Soc.  1983,  105:  2831 
• 9b Matsumura Y. Fujiwara J. Maruaka K. Yamamoto H. J. Am. Chem. Soc.  1983,  105:  6312