A new access to substituted tetraethyl N-Boc 2-aminoethylidene-1,1-bisphosphonates and phosphonyl-substituted aza-Morita-Baylis-Hillman-type adducts

Tetrahedron

Volumn 64, Issue 7, 2008, Pages 1233-1241

  Gajda, Anna ^a   Gajda, Tadeusz ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Amidosulfones; Aza Morita Baylis Hillman type adducts; Bisphosphonates; N Boc imines; Nucleophilic addition

Indexed keywords

ALENDRONIC ACID; BISPHOSPHONIC ACID DERIVATIVE; DIETHYL[1 TERT BUTOXYCARBONYLAMINO CYCLOHEXYLMETHYL)VINYL]PHOSPHONATE; DIETHYL[1 TERT BUTOXYCARBONYLAMINO NAPHTHALEN 1 YLMETHYL)VINYL]PHOSPHONATE; DIETHYL[1 TERT BUTOXYCARBONYLAMINO PHENYLMETHYL)VINYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL) 2 FURAN 2 YLETHYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL) 2 NAPHTHALEN 3 YLETHYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL) 2 PHENYLETHYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL) 2 PYRIDIN 2 YLETHYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL) 2 PYRIDIN 3 YLETHYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL) 3 METHYLBUTYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL)BUTYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL)HEXYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 (DIETHOXYPHOSPHORYL)PROPYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 METHYLENE BUTYL)PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 1 METHYLENE PROPYL)PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 2 CYCLOHEXYL 1 (DIETHOXYPHOSPHORYL)ETHYL]PHOSPHONATE; DIETHYL[2 TERT BUTOXYCARBONYLAMINO 3 METHYL 1 METHYLENE BUTYL)PHOSPHONATE; N TERT BUTYLOXYCARBONYL 2 AMINOETHYLIDENE 1,1 BIPHOSPHONATE DERIVATIVE; PAMIDRONIC ACID; RISEDRONIC ACID; UNCLASSIFIED DRUG; ZOLEDRONIC ACID;

ARTICLE; BAYLIS HILLMAN REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; ONE POT SYNTHESIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 37648999161     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.11.072     Document Type: Article

References (64)

1. Green J.R. J. Organomet. Chem. 690 (2005) 2439
2. Rosen L.S., Gordon D.H., Dugan Jr. W., Major P., Eisenberg P.D., Provenher L., Kaminski M., Simeone J., Seaman J., Chen B.L., and Coleman R.E. Cancer 100 (2004) 36
3. Kotsikorou E., and Oldfield E. J. Med. Chem. 46 (2003) 2932
4. Fleish H. Breast Cancer Res. 4 (2002) 30
5. Widler L., Jaeggi K.A., Glatt M., Müller K., Bachmann R., Bisping M., Born A.-R., Cortesi R., Guiglia G., Jeker H., Klein R., Ramseier U., Schmid J., Schreiber G., Seltenmeyer Y., and Green J.R. J. Med. Chem. 45 (2002) 3721
6. Montalavetti A., Bailey B.N., Martin M.B., Severin G.W., Oldfield E., and Docampo R. J. Biol. Chem. 276 (2001) 33930
7. Russell R.G.G. Phosphorus, Sulfur Silicon 146 (1999) 793
8. Kotsikorou E., Song Y., Chan J.M.W., Faelens S., Tovian Z., Broderick E., Bakalara N., Docampo R., and Oldfield E. J. Med. Chem. 48 (2005) 6128
9. Ghosh S., Chan J.M.W., Lea C.R., Meints G.A., Lewis J.C., Tovian Z.S., Flessner R.M., Loftus T.C., Bruchhaus I., Kendrick H., Croft S.L., Kemp R.G., Kobayashi S., Nozaki T., and Oldfield E. J. Med. Chem. 47 (2004) 175
10. Martin M.B., Sanders J.M., Kendrick H., de Luca-Fradley K., Lewis J.C., Grimley J.S., van Brussel E.M., Olsen J.R., Meints G.A., Burzynska A., Kafarski P., Croft S.L., and Oldfield E. J. Med. Chem. 45 (2002) 2904
11. Sanders J.M., Ghosh S., Chan J.M.W., Meints G., Wang H., Raker A.M., Song Y., Colantino A., Burzynska A., Kafarski P., Morita C.T., and Oldfield E. J. Med. Chem. 47 (2004) 375
12. Thompson K., and Rogers M.J. J. Bone Miner. Res. 19 (2004) 278
13. Shull L.W., Wiemer A.J., Hohl R.J., and Wiemer D.A. Bioorg. Med. Chem. 14 (2006) 4130
14. Sanders J.M., Song Y., Chan J.M.W., Zhang Y., Jennings S., Kosztowski T., Odeh S., Flessner R., Schwerdtfeger C., Kotsikorou E., Meints G.A., Gómez A.O., González-Pacanowska D., Raker A.M., Wang H., van Beek E.R., Papapoulos S.E., Morita C.T., and Oldfield E. J. Med. Chem. 48 (2005) 2957
15. Ebetino F.H., Rozé C.N., McKenna C.E., Barnett B.L., Dunford J.E., Russell R.G.G., Mieling G.E., and Rogers M.J. J. Organomet. Chem. 690 (2005) 2679
16. Szajnman S.H., Ravaschino E.L., Docampo R., and Rodriguez J.B. Bioorg. Med. Chem. Lett. 15 (2005) 4685
17. Sanders J.M., Gómez A.O., Mao J., Meints G.A., van Brussel E.M., Burzynska A., Kafarski P., González-Pacanowska D., and Oldfield E. J. Med. Chem. 46 (2003) 5171
18. Szajnman S.H., Montalavetti A., Wang Y., Docampo R., and Rodriguez J.B. Bioorg. Med. Chem. Lett. 13 (2003) 3231
19. Hutchinson D.W., and Thornton D.M. J. Organomet. Chem. 346 (1988) 341
20. Takeuchi M., Sakamoto S., Yoshida M., Abe T., and Isomura Y. Chem. Pharm. Bull. 41 (1993) 688
21. Bailly T., and Burgada R. Phosphorus, Sulfur Silicon 86 (1994) 217
22. Takeuchi M., Sakamoto S., Kawamuki K., Kurihara H., Nakahara H., and Isomura Y. Chem. Pharm. Bull. 46 (1998) 1703
23. Herczegh P., Buxton T.B., McPherson III J.C., Kovács-Kulyassa A., Brewer P.D., Sztaricskai F., Stroebel G.G., Plowman K.M., Farcasiu D., and Hartmann J.F. J. Med. Chem. 45 (2002) 2338
24. Inoue S., Okauchi T., and Minami T. Synthesis (2003) 1971
25. Couthon-Gourvès H., Simon G., Haelters J.-P., and Corbel B. Synthesis (2006) 81
26. Sturtz G., Appere G., Breistol K., Fodstad O., Schwartsmann G., and Hendriks H.R. Eur. J. Med. Chem. Chim. Ther. 27 (1992) 825
27. Storz T., and Vasella A. Helv. Chim. Acta 81 (1998) 1896
28. Couthon H., Gourvès J.-P., Guervenou J., Corbel B., and Sturtz G. Synth. Commun. 29 (1999) 4251
29. Kieczykowski G.R., Jobson R.B., Melillo D.G., Reinhold D.F., Grenda V.J., and Shinkai I. J. Org. Chem. 60 (1995) 8310
30. Griffiths D.V., Hughes J.M., Brown J.W., Caesar J.C., Swetnam S.P., Cumming S.A., and Kelly J.D. Tetrahedron 53 (1997) 17815
31. For recent applications of α-amidosulfones, see:
32. Petrini M., and Torregiani E. Synthesis (2007) 159
33. Petrini M. Chem. Rev. 105 (2005) 3949
34. Nejman M., Śliwińska A., and Zwierzak A. Tetrahedron 61 (2005) 8536
35. Desrosiars J.-N., Côté A., and Charette A.B. Tetrahedron 61 (2005) 6186
36. Côté A., Boezio A.A., and Charette A.B. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5405
37. Banphavichit V., Chaleawlertumpon S., Bhanthumnavin W., and Vilaivan T. Synth. Commun. 34 (2004) 3147
38. Mikolajczyk M., Grzejszczak S., Midura W., and Zatorski A. Synthesis (1976) 396
39. Zwierzak A., and Pilichowska S. Synthesis (1982) 922
40. Greene T.W., and Wuts P.G.M. In: Greene T.W., and Wuts P.G.M. (Eds). Protective Groups In Organic Synthesis (1999), John Wiley and Sons, New York, NY 520
41. McKenna C.E., Higa M.T., Cheung N.H., and McKenna M.C. Tetrahedron Lett. 2 (1977) 155
42. McKenna C.E., and Schmidhauser J. J. Chem. Soc., Chem. Commun. (1979) 739
43. Maryanoff B.C., and Reitz A.B. Chem. Rev. 89 (1989) 863
44. Hullar T.L. J. Med. Chem. 5 (1969) 58
45. For recent synthesis of α-alkylidene-β-amino acid esters by the HWE reaction of protected 3-amino-2-(diethoxyphosphoryl)alkanoates, see:. Wa{ogonek}sek T., Olczak J., and Janecki T. Synlett (2006) 1507
46. For recent reviews, see:
47. Shi Y.-L., and Shi M. Eur. J. Org. Chem. (2007) 2905
48. Masson G., Housseman C., and Zhu J. Angew. Chem., Int. Ed. 46 (2007) 4614
49. Raheem I.T., and Jacobsen E.N. Adv. Synth. Catal. 347 (2005) 1701
50. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811
51. Sergeeva N.N., Golubev A.S., Hennig L., and Burger K. Synthesis (2003) 915
52. For the synthesis of N-alkyl aza-MBH-type adducts, see:
53. Krawczyk H. Synth. Commun. 24 (1994) 2263
54. Gurevich I.E., and Tebby J.C. J. Chem. Soc., Perkin Trans. 1 (1995) 1259
55. Krawczyk H. Phosphorus, Sulfur Silicon 101 (1995) 221
56. Ghelfi F., Stevens C.V., Laureyn I., Van Meenen E., Rogge T.M., De Buyck L., Nikitin K.V., Grandi R., Libertini E., Pagnoni U.M., and Schnetti L. Tetrahedron 59 (2003) 1147
57. Loreto M.A., Pompili C., and Tardella P.A. Tetrahedron 57 (2001) 4423
58. Francavilla M., Gasperi T., Loreto M.A., Tardella P.A., and Basetti M. Tetrahedron Lett. 43 (2002) 7913
59. Park H., Cho C.-W., and Krische M.J. J. Org. Chem. 71 (2006) 7892
60. Hormi O.E.O., Pajunen E.O., Avall A.-K.O., and Pennanen P. Synth. Commun. 20 (1990) 1865
61. Engeberts J.B.F.N., and Strating J. Recl. Trav. Chim. Pays-Bas 83 (1964) 733
62. Kanazawa A.M., Denis J.-N., and Greene A.E. J. Org. Chem. 59 (1994) 1238
63. Bernacka E., Klepacz A., and Zwierzak A. Tetrahedron Lett. 42 (2001) 5093
64. Klepacz A., and Zwierzak A. Tetrahedron Lett. 43 (2002) 1079