Synthesis and reactivity of azidoalkylphosphonates, -phosphinates and -phosphine oxides

Current Organic Chemistry

Volumn 11, Issue 18, 2007, Pages 1652-1668

  Gajda, Anna ^a   Gajda, Tadeusz ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORUS COMPOUNDS;

AZIDO GROUP; HALOGEN DERIVATIVES; HYDROXYDERIVATIVE; NUCLEOPHILIC SUBSTITUTIONS; PHOSPHINATE; PHOSPHINE OXIDE; PHOSPHINIC ACID; PHOSPHONATES; SULFONATE DERIVATIVES; SYNTHETIC ROUTES;

SULFUR COMPOUNDS;

ALPHA AMINOPHOSPHONATE; ALPHA AZIDOALKYLPHOSPHINATE; ALPHA AZIDOALKYLPHOSPHINE OXIDE; ALPHA AZIDOALKYLPHOSPHONATE; AZIDE; AZIDOALKYLPHOSPHINATE; AZIDOALKYLPHOSPHINE OXIDE; AZIDOALKYLPHOSPHONATE; BETA AZIDOALKYLPHOSPHINATE; BETA AZIDOALKYLPHOSPHINE OXIDE; BETA AZIDOALKYLPHOSPHONATE; CYANAMIDE; DIPEPTIDE; EPOXIDE; HETEROCYCLIC COMPOUND; IMINE; ISOTHIOCYANIC ACID DERIVATIVE; ORGANIC COMPOUND; ORGANOHALOGEN DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PHOSPHONODIPEPTIDE; PHOSPHORUS DERIVATIVE; SULFATE; SULFITE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONFERENCE PAPER; CYCLOADDITION; ELECTROPHILIC AZIDATION; HYDROGENATION; MITSUNOBU REACTION; NUCLEOPHILIC AZIDATION; NUCLEOPHILIC SUBSTITUTION; RING OPENING; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 37449011645     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527207783221219     Document Type: Conference Paper

References (106)

1. Scriven, E.F.V.; Turnbull, K. Chem. Rev., 1988, 88, 297.
2. Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
3. Panchaud, P.; Chabaud, L.; Landais, Y.; Ollivier, C.; Renaud, P.; Zigmantas, S. Chem. Eur. J., 2004, 10, 3606.
4. Brase, S.; Gil, C.; Knepperl K.; Zimmermann, V. Angew. Chem. Int. Ed., 2005, 44, 5188.
5. Moonen, K.; Laureyn, I.; Stevens, C. V. Chem. Rev., 2004, 104, 6177.
6. Palacios, F.; Alonso, C.; de los Santos, J.M. Chem. Rev., 2005, 105, 899.
7. Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de los Santos, J.M. Tetrahedron, 2007, 63, 523.
8. Mitsunobu, O. Synthesis, 1980, 1.
9. Hughes, D. L. In Organic Reactions; Wiley: New York, 1988; Vol. 42, pp. 335-656.
10. Hughes, D.L. Org. Prep. Proc. Int., 1996, 28, 127.
11. Wisniewski, K.; Kołodziejczyk, A.S.; Falkiewicz, B. J. Pept. Sci., 1998, 4, 1.
12. Dembinski, R. Eur. J. Org. Chem., 2004, 2763.
13. Dandapani, S.; Curran, D.P. Chem. Eur. J., 2004, 10, 3130.
14. Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn., 1967, 40, 2380.
15. Hammerscbmidt, F.; Völlenkle, H. Liebigs Ann. Chem., 1989, 577.
16. Gajda, T.; Matusiak, M. Synthesis, 1992, 367.
17. Hammerschmidt, F.; Wuggening, F. Phosphorus Sulfur Silicon, 1998, 141, 231.
18. Hammerschmidt, F.; Wuggening, F. Tetrahedron Asymmetry, 1999, 10, 1709.
19. Öhler, E.; Kotzinger, S. Liebigs Ann. Chem., 1993, 269.
20. Öhler, E.; Kotzinger, S. Liebigs Ann. Chem., 1994, 867.
21. Gajda, T.; Matusiak, M. Synth. Commun., 1992, 22, 2193.
22. Gajda, T.; Matusiak, M. Phosphorus Sulfur Silicon, 1993, 77, 192.
23. Gajda, T. Tetrahedron Asymmetry, 1994, 5, 1965.
24. Yokomatsu, T.; Shibuya, S. Tetrahedron Asymmetry, 1992, 3, 377.
25. Hammerschmidt, F.; Hanbauer, M. J. Org. Chem., 2000, 65, 6121.
26. Drescher, M.; Li, Y.-F.; Hammerschmidt, F. Tetrahedron, 1995, 51, 4933.
27. Wuggening, F.; Hammerschmidt, F. Monatsh. Chem., 1998, 129, 423.
28. Drescher, M.; Felsinger, S.; Hammerschmidt, F.; Kählig, H.; Schmidt, S.; Wuggenig, F. Phosphorus Sulfur Silicon, 1998, 140, 79.
29. Skropeta, D.; Schwörer, R.; Schmidt, R.R. Bioorg. Med. Chem. Lett., 2003, 13, 3351.
30. Skropeta, D.; Schmidt, R.R. Tetrahedron Asymmetry, 2003, 14, 265.
31. Yokomatsu, T.; Yoshida, Y.; Shibuya, S. J. Org. Chem., 1994, 59, 7930.
32. Bongini, A.; Camerini, R.; Panunzio, M. Tetrahedron Asymmetry, 1996, 7, 1467.
33. Simov, B.P.; Wuggening, F.; Lämmerchofer, M.; Lindner, W.; Zarbl. E.; Hammerschmidt, F. Eur. J. Org. Chem., 2002, 1139.
34. Gajda, T. Phosphorus Sulfr Silicon, 1993, 85, 59.
35. Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron, 2004, 60, 203.
36. Khokhlov, P.S.; Osipov, V.N.; Kolesova, B.A. Zh. Obshsch. Khim., 1990, 60, 1669.
37. Hanaya, T.; Miyoshi, A.; Kawamoto, H.; Armour, M.-A.; Hogg, A.M.; Yamamoto, H. Bull. Chem. Soc. Jpn., 1990, 63, 3590.
38. Palacios, F.; Ochoa de Retana, A.M.; Pagalday, J. Eur. J. Org. Chem., 2003, 913.
39. Flohr, A.; Aemissegger, A.; Hilvert, D. J. Med. Chem., 1999, 42, 2633.
40. Lohray, B.B.; Maji, D.K.; Nandann, E. Ind. J. Chem., 1995, 34B, 1023.
41. Clayden, J.; McElroy, A.B.; Warren, S. J. Chem. Soc. Perkin Trans. 1, 1995, 1913.
42. Waschbüsch, R.; Carran, J.; Marinetti, A.; Savignac, P. Chem. Rev., 1997, 97, 3401.
43. Hanessian, S.; Bennani, Y.L. Tetrahedron Lett., 1990, 31, 6465.
44. Hanessian, S.; Bennani, Y.L.; Delorme, D. Tetrahedron Lett., 1990, 31, 6461.
45. Battersby, A.R.; Block, M.H.; Fookes, J.R.; Harrison, P.J.; Henderson, G.M.; Leeper, F.J. J. Chem. Soc. Perkin Trans. 1, 1992, 2175.
46. Berté-Verrando, S.; Nief, F.; Patois, C.; Savignac, P. Phosphorus Sulfur Silicon, 1995, 103, 91.
47. Mortier, J.; Gridnev, I.D.; Fortineau, A.-D. Org. Lett., 1999, 1, 981.
48. Chakraborty, S.K.; Engel, R. Synth. Commun., 1991, 21, 1039.
49. Berté-Verrando, S.; Nief, F.; Patois, C.; Savignac, P. J. Chem. Soc. Perkin Trans. 1, 1995, 2045.
50. Elachqar, A.; El Hallaoui, A.; Roumestant, M.L.; Viallefont, Ph. Synth. Commun., 1994, 24, 1279.
51. Cairns, J.; Dunne, C.; Franczyk, T.S.; Hamilton, R.; Hardacre, C.; Stern, M.K.; Treacy, A.; Walker, B.J. Phosphorus Sulfur Silicon, 1999, 144-146, 385.
52. Maraval, V.; Prévôté-Pinet, D.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. New J. Chem., 2000, 24, 561.
53. Seyferth, D.; Hilbert, P. Org. Prep. Proc. Int., 1971, 3, 51.
54. Koichi, I.; Akihito, I.; Mitsuji, Y. Synthesis, 1989, 595.
55. Hakimelahi, G.H.; Just, G. Synth. Commun., 1980, 10, 429.
56. Khokhlov, P.S.; Osipov, V.N.; Kashemirov, B.A. Zh. Obshch. Khim., 1992, 62, 470.
57. Denmark, S.E.; Chatani, N.; Pansare, S.V. Tetrahedron, 1992, 48, 2191.
58. Hanessian, S.; Bennani, Y.L. Synthesis, 1994, 1272.
59. Guéguen, C.; About-Jaudet, E.; Collignon, N.; Savignac, P. Synth. Commun., 1996, 26, 4131.
60. Kukhar, V. P.; Hudson, H. R. Aminophosphonic Aminophosphinic Acids Chemistry and Biological Activity, John Wiley: Chichester, 2000.
61. Kafarski, P.; Mastalerz, P. Aminophosphonates. Natural occurrence, biochemistry and biological properties, Beiträge zur Wirkstofforschung, Berlin, 1984, vol. 21.
62. Berté-Verrando, S.; Diziere, R.; Samadi, M.; Savignac, P. J. Chem. Soc. Perkin Trans. 1, 1995, 3125.
63. Staudinger, H.; Hauser, E. Helv. Chim. Acta, 1921, 4, 861.
64. Barluenga, J.; Palacios, F. Org. Prep. Proc. Int., 1991, 23, 1.
65. Gololobov, Y.G.; Kasukhin, L.F. Tetrahedron, 1992, 48, 1353.
66. Fresneda, P. M.; Molina, P. Synlett, 2004, 1.
67. Harwig, C.W.; Hoffman, T.Z.; Wentworth, A.D.; Janda, K.M. Bioorg. Med. Chem. Lett., 2000, 10, 915.
68. Gajda, T.; Sikora, D.; Nonas, T. Phosphorus Sulfur Silicon, 1999, 144-146, 581.
69. Gajda, T.; Janik, D. Pol. J. Chem., 2005, 79, 493.
70. Sikora, D.; Ph.D. Thesis, Lodz, 2002.
71. Koziara, A.; Zwierzak, A. Tetrahedron Lett., 1987, 28, 6513.
72. Koziara, A. J. Prak. Chem., 1988, 330, 473.
73. Zwierzak, A.; Koziara, A. Phosphorus Sulfur, 1987, 30, 331.
74. Palacios, F.; Ochoa de Retana, A.M.; Martínez de Margirota, E.; Rodriguez, M.; Pagalday, J. Tetrahedron, 2003, 59, 2617.
75. Palacios, F.; Alonso, C.; Pagalday, J.; Ochoa de Retana, A.M.; Rubiales, G. Org. Biomol. Chem., 2003, 1, 1112.
76. Katritzky, A.R.; Zhang, G.; Jiang, J. J. Org. Chem., 1994, 59, 4556.
77. Sikora, D.; Gajda, T. Phosphorus Sulfur Silicon, 2000, 157, 201.
78. Sikora, D.; Gajda, T. Tetrahedron, 2000, 56, 3755.
79. Sikora, D.; Nonas, T.; Gajda, T. Tetrahedron, 2001, 57, 1619.
80. Fan, W.-Q.; Katritzky, A.R. In Comprehensive Heterocyclic Chemistry II, Katritzky, A.R.; Rees, C.; Scriven, E.F.V., Eds. Elsevier Science Ltd. Oxford, 1996, vol. 4, pp. 2-126.
81. Padwa, A. In Comprehensive Organic Synthesis Eds., Trost, B.M.; Fleming, I. Pergamon Press, Shemmelhack, M. F., Ed, 1991; vol. 4, pp. 1069-1111.
82. Lwowski, W. In 1,3-Dipolar Cycloaddition Chemistry Ed. Padwa, A., Wiley Interscience, NY, 1984; vol. 1, pp. 559-651.
83. Palacios, F.; Ochoa de Retana, A.M.; Pagalday, J. Heterocycles, 1994, 38, 95.
84. Palacios, F.; Ochoa de Retana, A. M.; Pagalday, J. Heterocycles, 1995, 40, 543.
85. Louërat, F.; Bougorin, K.; Loupy, A.; Ochoa de Retana, A. M.; Pagalday, J.; Palacios, F.; Heterocycles, 1998, 48, 161.
86. Palacios, F.; Ochoa de Retana, A.M.; Pagalday, J. Org. Prep. Proc. Int., 1995, 27, 625.
87. Sikora, D.; Gajda, T. Synth. Commun., 1998, 28, 1215.
88. Achamlale, S.; Elachqar, A.; El Hallaoui, A.; Alami, A.; Elhaji, S.; Roumestant, M.L.; Viallefont, P. Phosphorus Sulfur Silicon, 1998, 140, 103.
89. Mikołajczyk, M.; Drabowicz, J.; Łyzwa, P. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E.; Soloshonok, V.A., Eds. John Wiley: Hoboken, NJ, 2005; pp. 261-276.
90. Palacios, F.; Alonso, C.; de los Santos, J.M. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E.; Soloshonok, V.A., Eds.; John Wiley: Hoboken, NJ, 2005; pp. 277-318.
91. Gajda, T.; Nowalińska, M.; Zawadzki, S.; Zwierzak, A. Phosphorus Sulfur Silicon, 1995, 105, 45.
92. Woschek, A.; Lindner, W.; Hammerschmidt, F. Adv. Synth. Catal., 2003, 345, 1287.
93. Xu, C.; Yuan, C. Eur. J. Org. Chem., 2004, 4410.
94. Malakhov, D.V.; Semizarov, D.G.; Yas'ko, M.V. Bioorg. Khim., 1995, 21, 539.
95. Blass, B.E.; Coburn, K.R.; Faulkner, A.L.; Seibel, W.L.; Srivastava, A. Tetrahedron Lett., 2003, 44, 2153.
96. Dreef, C.E.; Valentijn, A.R.P.M.; de Vroom, E.; van der Marel, G.A.; van Boom, J.H. Tetrahedron Lett., 1988, 29, 1199.
97. van der Klein, P.A.M.; Boons, G.J.P.H.; Veeneman, G.H.; van der Marel, G.A.; van der Boom, J.H. Tetrahedron Lett., 1989, 30, 5473.
98. Hammerschmidt, F.; Lindner, F.; Wuggenig, F.; Zarbl, E. Tetrahedron Asymmetry, 2000, 11, 2955.
99. Penz, G.; Zbiral, E. Chem. Ber., 1985, 118, 4131.
100. Verbrugen, C.; De Craecker, S.; Rajan, P.; Jiao, X.-Y.; Borloo, M.; Smith, K.; Fairlamb, A.H.; Haemers, A. Bioorg. Med. Chem. Lett., 1996, 6, 253.
101. Mitchell, M.; Qaio, L.; Wong, C.-H. Adv. Synth. Catal., 2001, 343, 596.
102. Yamagishi, T.; Fujii, K.; Shibuya, S.; Yokomatsu, T. Synlett, 2004, 2505.
103. Liotta, L.J.; Gibbs, R.A.; Taylor, S.C.; Benkovic, P.A.; Benkovic, S.J. J. Am. Chem. Soc., 1995, 117, 4729.
104. Reyes-Rangel, G.; Marañón, V.; Avila-Ortiz, G.; Anaya de Parrodi, C.; Quintero, L.; Juaristi, E. Tetrahedron, 2006, 62, 8404.
105. Anaya de Parrodi, C.; Juaristi, E. Synlett, 2006, 2699.
106. Dolence, E.K.; Roylance, J.B. Tetrahedron Asymmetry, 2004, 15, 3307.