Synthesis 2004(15): 2441-2444  
DOI: 10.1055/s-2004-831233
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Mingshu Wu, Ruyu Chen*, You Huang*
Institute and National Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Fax: +86(22)23503438; e-Mail: wums@eyou.com;
Further Information

Publication History

Received 1 March 2004
Publication Date:
22 September 2004 (online)

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.

    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