A microwave-assisted solvent- and catalyst-free synthesis of aminomethylene bisphosphonates

Tetrahedron Letters

Volumn 50, Issue 29, 2009, Pages 4243-4245

  Kaboudin, Babak ^a   Alipour, Soheil ^a  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BISPHOSPHONIC ACID DERIVATIVE; CARBENE; FORMIC ACID DERIVATIVE; PHOSPHITE; SOLVENT;

ARTICLE; CATALYST; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME;

EID: 66349095116     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.016     Document Type: Article

References (65)

1. Engel R. Chem. Rev. 77 (1977) 349-367
2. Moonen K., Laureyn I., and Stevens C.V. Chem. Rev. 104 (2004) 6177-6215
3. Collinsova M., and Jiracek J. Curr. Med. Chem. 7 (2000) 629-647
4. Kafarski P., Lejczak B., Tyka R., Koba L., Pliszczak E., and Wieczorek P. J. Plant Growth Regul. 14 (1995) 199-203
5. Ishiguri, Y.; Yamada, Y.; Kato, T.; Sasaki, M.; Mukai, K. Eur. Pat. Appl., EP 82-301905, 1982; Chem. Abstr. 1983, 98, 102686.
6. Gancarz R., and Chakraborty S. Synthesis (1977) 625
7. Giannousis P.P., and Bartlett P.A. J. Med. Chem. 30 (1987) 1603-1609
8. Maier L., and Lea P.J. Phosphorus, Sulfur Silicon 17 (1983) 1-19
9. Hilderbrand R.L. The Role of Phosphonates in Living Systems (1982), CRC Press, Boca Raton, F1
10. Kafarski P., and Lejczak B. Phosphorus, Sulfur Silicon 63 (1991) 193-215
11. Kukhar V.P., and Hudson H.R. Aminophosphonic and Aminophosphinic Acids (2000), John Wiley & Sons
12. Hanessian S., and Bennani Y.L. Synthesis (1995) 1272
13. Redmore D. In: Griffith E.J., and Grayson M. (Eds). Topics in Phosphorus Chemistry Vol. 8 (1976), Wiley, New York
14. Atherton F.R., Hassall C.H., and Lambert R.W. J. Med. Chem. 29 (1986) 29-40
15. Allen M.C., Fuhrer W., Tuck B., Wade R., and Wood J.M. J. Med. Chem. 32 (1989) 1652-1661
16. Hassall C.H. In: Hahn F.E. (Ed). Antibiotics Vol. VI (1983), Springer, Berlin 1-11
17. Gancarz R., and Wieczorek J.S. Synthesis 625 (1978)
18. Seyferth D., Marmor R.S., and Hilbert P. J. Org. Chem. 36 (1971) 1379-1386
19. Worms K.H., and Schmidt-Dunker M. In: Kosolapoff G.M., and Marier L. (Eds). Organic Phosphorus Compounds Vol. 7 (1976), John Wiley & Sons, New York 1
20. Kaboudin B. Phosphorus, Sulfur Silicon 177 (2002) 1749-1751
21. Bhagat S., and Chakraborti A.K. J. Org. Chem. 72 (2007) 1263-1270
22. Barycki J., Mastalerz P., and Soroka M. Tetrahedron Lett. 36 (1970) 3147-3150
23. Kaboudin B., and Sorbiun M. Tetrahedron Lett. 48 (2007) 9015-9017
24. Genet J.P., Uziel J., Port M., Touzin A.M., Roland S., Thorimbert S., and Tanier S. Tetrahedron Lett. 33 (1992) 77-80
25. Qian C., and Huang T. J. Org. Chem. 63 (1998) 4125-4128
26. Ranu B.C., Hajira A., and Jana U. Org. Lett. 1 (1999) 1141-1143
27. Manabe K., and Kobayashi S. Chem. Commun. (2000) 669-670
28. Chandrasekhar S., Prakash S.J., Jagadeshwar V., and Narsihmulu C. Tetrahedron Lett. 42 (2001) 5561-5563
29. Abdou W.M., and Shaddy A.A. Arkivoc ix (2009) 143-182
30. Gittens S.A., Bansal G., Zernicke R.F., and Uludaǧ H. Adv. Drug. Delivery Rev. 57 (2005) 1011-1036
31. Kavanagh K.L., Guo K., Dunford J.E., Wu X., Knapp S., Ebetino F.H., Rogers M.J., Russel R.G.G., and Opermann U. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 7829-7834
32. Sanders J.M., Gómez A.O., Mao J., Meints G.A., Van Brussel E.M., Burzynska A., Kafarski P., Gonzáles-Pacanowska D., and Oldfield E. J. Med. Chem. 46 (2003) 5171-5183
33. Martin M.B., Grimley J.S., Lewis J.C., Heath III H.T., Bailey B.N., Kendrick H., Yardley V., Caldera A., Lira R., Urbina J.A., Moreno S.N., Docampo R., Croft S.L., and Oldfield E. J. Med. Chem. 44 (2001) 909-916
34. Kotsikorou E., Song Y., Chan J.M.W., Faelens S., Tovian Z., Broderick E., Bakarala N., Docampo R., and Oldfield E. J. Med. Chem. 48 (2005) 6128-6139
35. Lecerclé D., Gabillet S., Gomis J.-M., and Taran F. Tetrahedron Lett. 49 (2008) 2083-2087
36. Pudovik A.N., and Konovalova I.V. Synthesis (1979) 81-96
37. Maier L. Phosphorus, Sulfur 11 (1981) 311-322
38. Takeuchi M., Sakamoto S., Yoshida M., Abe T., and Isomura Y. Chem. Pharm. Bull. 41 (1993) 688-693
39. Soloducho, J.; Gancarz, R.; Wieczorek, P.; Korf, J.; Hafner, J.; Lejczak, B.; Kafarski, P. Patent PL93-298436 93408, 1993; Chem Abstr. 1998, 128, 61631.
40. Prishchenko A.A., Livantsov M.V., and Petrosyan V.S. Zh. Obshch. Kim. 63 (1993) 1902 Chem. Abstr. 1994, 120, 217906
41. Wu M., Chen R., and Huang Y. Synth. Commun. 34 (2004) 1393-1398
42. Yokomatsu T., Yoshida Y., Nakabayashi N., and Shibuya S. J. Org. Chem. 59 (1994) 7562-7564
43. Krutikov V.I., Erkin A.V., Pautov P.A., and Zolotukhina M.M. Russ. J. Gen. Chem. 73 (2003) 187
44. Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284
45. Loupy A., and Perreux L. Tetrahedron 57 (2001) 9199-9223
46. Kaboudin B., and Nazari R. Tetrahedron Lett. 42 (2001) 8211
47. Kaboudin B. Tetrahedron Lett. 43 (2002) 8713-8714
48. Kaboudin B. Tetrahedron Lett. 44 (2003) 1051-1053
49. Kaboudin B., Haghighat H., and Yokomatsu T. J. Org. Chem. 71 (2006) 6604-6606
50. Kaboudin B. Chem. Lett. (2001) 880-881
51. Kaboudin B., and Nazari R. Synth. Commun. 31 (2001) 2245-2250
52. Kaboudin B., and Rahmani A. Synthesis (2003) 2705-2708
53. Kaboudin B., and Saadati F. Synthesis (2004) 1249-1252
54. Kaboudin B., and Rahmani A. Org. Prep. Proced. Int. 36 (2004) 82-86
55. Kaboudin B., and Moradi K. Tetrahedron Lett. 46 (2005) 2989-2991
56. Kaboudin B., and Haghighat H. Tetrahedron Lett. 46 (2005) 7955-7957
57. Kaboudin B., and Karimi M. Bioorg. Med. Chem. Lett. 16 (2006) 5324-5327
58. Kaboudin B., and Moradi K. Synthesis (2006) 2339-2342
59. Kaboudin B., and Jafari E. Synthesis (2006) 3063-3066
60. Kaboudin B., and Farjadian F. Beilstein J. Org. Chem. 2 (2006) 4
61. Yamagishi T., Kusano T., Kaboudin B., Yokomatsu T., Sakuma C., and Shibuya S. Tetrahedron 59 (2003) 767-772
62. Kaboudin B., Haruki T., Yamaghishi T., and Yokomatsu T. Tetrahedron 63 (2007) 8199-8205
63. Kaboudin B., Haruki T., Yamagishi T., and Yokomatsu T. Synthesis (2007) 3226-3232
64. Kaboudin B., Haghighat H., and Yokomatsu T. Tetrahedron: Asymmetry 19 (2008) 862-866
65. PC = 146.5 Hz), 63.5-64.0 (m), 106.3, 118.5, 120.6, 123.4, 125.5, 126.3, 126.7, 128.7, 134.2, 141.5.