New synthesis of gem-bis(phosphono)ethylenes and their applications

Synthesis

Volumn , Issue 13, 2003, Pages 1971-1976

  Inoue, Susumu ^a   Okauchi, Tatsuo ^a   Minami, Toru ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Bis(phosphono)ethylene; Heterocycles; Michael addition; Palladium catalyzed cross coupling reaction; Phosphonic acid

Indexed keywords

HALOGENATION; POTASSIUM COMPOUNDS; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

REAGENTS;

POLYETHYLENES;

1 (DIBENZYLPHOSPHONO) 1 (DIETHYLPHOSPHONO)ETHYLENE; 1,1 BIS(DIETHYLPHOSPHONO) 2 PHENYLETHYLENE; 1,1 BIS(DIETHYLPHOSPHONO)ETHYLENE; 1,1 BIS(DIETHYLPHOSPHONO)PROP 1 ENE; 2,2 DIBROMO 1,1 BIS(DIETHYLPHOSPHONO)CYCLOPROPANE; 3,3,3 TRIBROMO 1,1 BIS(DIETHYLPHOSPHONO)PROPANE; BISPHOSPHONIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; LITHIUM DERIVATIVE; N (4 TOLUENESULFONYL) 2,2 BIS(DIETHYLPHOSPHONO)AZIRIDINE; N (METHANESULFONYL) 2,2 BIS(DIETHYLPHOSPHONO)AZIRIDINE; PALLADIUM; POTASSIUM; UNCLASSIFIED DRUG; [1 CHLORO 2 (1 IMIDAZOLYL)ETHYL] 1,1 BIS(DIETHYLPHOSPHONATE); [1 CHLORO 2 (3 PYRIDYL)ETHYL] 1,1 BIS(DIETHYLPHOSPHONATE); [1 FLUORO 2 (1 IMIDAZOLYL)ETHYL] 1,1 BIS(DIETHYLPHOSPHONATE); [1 FLUORO 2 (3 PYRIDYL)ETHYL] 1,1 BIS(DIETHYLPHOSPHONATE);

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; DRUG SYNTHESIS; HALOGENATION; INFRARED SPECTROSCOPY; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0141594908     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41002     Document Type: Article

References (38)

1. (a) Fleisch, H. Bisphosphonates in Bone Disease; The Parthenon Publishing Group: New York, 1997.
2. (b) Russell, R. G. G. Phosphorous, Sulfur Silicon Relat. Elem. 1999, 144-146, 793.
3. (c) Gowen, M.; Emery, J. G.; Kumar, S. Emerging Drugs 2000, 5, 1; Chem. Abstr. 2000, 132, 231375.
4. (c) Gowen, M.; Emery, J. G.; Kumar, S. Emerging Drugs 2000, 5, 1; Chem. Abstr. 2000, 132, 231375.
5. (a) Nicholson, D. A.; Cilley, W. A.; Quimby, O. T. J. Org. Chem. 1970, 35, 3149.
6. (b) Richard, J. J.; Burke, K. E.; O'Laughlin, J. W.; Banks, C. V. J. Am. Chem. Soc. 1961, 83, 1722.
7. (c) Czekaski, T.; Gross, H.; Costisella, B. J. Prakt. Chem. 1982, 324, 537.
8. (d) Iorga, B.; Savignac, P. J. Organomet. Chem. 2001, 624, 203.
9. (e) Waschbüsch, R.; Carran, J.; Marinetti, A.; Savignac, P. Synthesis 1997, 727.
10. (f) Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572.
11. (g) Hutchinson, D. W.; Thornton, D. M. Synthesis 1990, 135.
12. (h) Yuan, C.; Li, C.; Ding, Y. Synthesis 1991, 854.
13. (a) Almstead, N. G.; Dansereau, S. M.; Francis, M. D.; Snider, C. M.; Ebentino, F. H. Phosphorous, Sulfur Silicon Relat. Elem. 1999, 144-146, 325.
14. (b) Page, P. C. B.; Moor, J. P. G.; Manfield, I.; McKenzie, M. J.; Bowler, W. B.; Gallagher, J. A. Tetrahedron 2001, 57, 1837.
15. (a) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
16. (b) Minami, T.; Okauchi, T.; Kouno, R. Synthesis 2001, 349.
17. (a) Lolli, M. L.; Lazzarato, L.; Stilo, A. D.; Fruttero, R.; Gasco, A. J. Organomet. Chem. 2002, 650, 77.
18. (b) Loussouarn, A.; Servant, G.; Guervenou, J.; Sturta, G. Phosphorous, Sulfur and Silicon 1996, 113, 275.
19. (c) Burgos-Lepley, C. E.; Mizsak, S. A.; Nugent, R. A.; Johnson, R. A. J. Org. Chem. 1993, 58, 4159.
20. (d) Sturtz, G.; Guervenou, J. Synthesis 1991, 661.
21. (a) Lehnert, W. Tetrahedron 1974, 30, 301.
22. (b) Caroll, R. L. German Patent, 2026078, 1971; Chem. Abstr. 1971, 74, 42486.
23. (b) Caroll, R. L. German Patent, 2026078, 1971; Chem. Abstr. 1971, 74, 42486.
24. (c) Degenhardt, C. R.; Burdsall, D. C. J. Org. Chem. 1986, 51, 3488.
25. Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337.
26. (a) Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 40, 13603.
27. (b) Pousset, C.; Larchevêque, M. Tetrahedron Lett. 2002, 43, 5257.
28. (a) Smith, W. W.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4622.
29. (b) Logusch, E. W.; Walker, D. M.; McDonald, J. F.; Leo, G. C.; Franz, J. E. J. Org. Chem. 1988, 53, 4069.
30. (c) Alonso, E.; Alonso, E.; Solís, A.; Pozo, C. Synlett 2000, 698.
31. (d) Large, G. B. Stauffer Co. US Patent 4170463, 1979; Chem. Abstr. 1980, 92, 164085.
32. (d) Large, G. B. Stauffer Co. US Patent 4170463, 1979; Chem. Abstr. 1980, 92, 164085.
33. (a) Evans, D. A.; Faul, M. M.; Biodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
34. (b) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
35. (a) Ebentino, F. H.; Bayless, A. V.; Amburgey, J.; Ibbotson, Kj.; Dansereau, S.; Ebrahimpour, A. Phosphorous, Sulfur Silicon Relat. Elem. 1996, 109-110, 217.
36. (b) Dauer, R. R.; Dimichele, L.; Futran, M.; Kieczykowski, G. R. US Patent 5510517, 1995; Chem. Abstr. 1996, 125, 33879.
37. (b) Dauer, R. R.; Dimichele, L.; Futran, M.; Kieczykowski, G. R. US Patent 5510517, 1995; Chem. Abstr. 1996, 125, 33879.
38. Cai, D.; Larsen, R. D.; Reider, P. J. Tetrahedron Lett. 2002, 43, 4285.