Hetero Diels-Alder (HDA) reactions of 1-Phosphono-1,3-butadienes with azo and nitroso dienophiles: An entry towards versatile heterocyclic synthons for aminophosphonic compounds

Targets in Heterocyclic Systems

Volumn 14, Issue , 2010, Pages 49-79

  Monbaliu, Jean Christophe ^a   Villemin, Elise ^a   Elias, Benjamin ^a   Marchand Brynaert, Jacqueline ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84874363423     PISSN: 17249449     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article

References (157)

1. Savignac, P., Iorga, B. Modern Phosphonate Chemistry; CRC Press, LLC: Boca Raton, 2003, p. 552.
2. Kukhar, V.P., Hudson, H.R. Aminophosphonic and Aminophosphonic acids: Chemistry and Biological Activity; John Wiley & Sons, Ltd: Chichester, 2000.
3. Hendlin, D., Stapley, E., Jackson, M., Wallik, H., Miller, A. et al. Science 1969, 166, 122.
4. Simoni, D., Gebbia, N., Invidiata, F.P., Eleopra, M., Marchetti, P. et al. J. Med. Chem. 2008, 51, 6800, and references cited therein.
5. Laber, B., Gerbling, K., Harde, C., Neff, K., Nordhoff, E., Pohlenz, H. Biochemistry 1994, 33, 3413.
6. Wermuth, C. The Practice of Medicinal Chemistry; Elsevier, Academic Press, 2006.
7. Miceli, M.V., Henderson, T.O., Myers, T.C. Science 1980, 209, 1245.
8. Baird, D., Upchurch, R., Homesley, W., Franz, J. Proceedings-North Central Weed Control Conference 1971, 26, 64.
9. Hashimoto, M., Hemmi, K., Takeno, H., Kamiya, T. Tetrahedron Lett. 1980, 21, 99.
10. Russel, R. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 146, 793.
11. Villar, H.O., Hansen, M.R. Curr. Top. Med. Chem. 2007, 7, 1509.
12. Hecker, S.J., Erion, M.D. J. Med. Chem. 2008, 51, 2328.
13. Romanenko, V.D., Kukhar, V.P. Chem. Rev. 2006, 106, 3868.
14. Deadman, J.J., Elgendy, S., Goodwin, C.A., Green, D., Baban, J.A. et al. J. Med. Chem. 1995, 38, 1511.
15. Aschi, M., Besker, N., Re, N., Pochetti, G., Coletti, C. et al. J. Med. Chem. 2007, 50, 211.
16. Han, L., Hiratake, J., Kamiyama, A., Sakata, K. Biochemistry 2007, 46, 1432.
17. Cruz-Gregorio, S., Rodriguez-Palacios, V., Höpfl, H., Quintero, L., Sartillo-Piscil, F. J. Org. Chem. 2009, 74, 197.
18. Karppinen, J., Yli-Pentti, A. Separation Sci. & Technol. 2000, 35, 1619.
19. Outala, P., Leinonen, H., Ridell, M., Lehto, J. Solvent Extraction & Ion Exchange 2001, 19, 743.
20. Bruyneel, F., D'Auria, L., Payen, O., Courtoy, P.J., Marchand-Brynaert, J. ChemBioChem 2010, 11, 1451.
21. Bruyneel, F., Payen, O., Rescigno, A., Tinant, B., Marchand-Brynaert, J. Chem.-Eur. J. 2009, 15, 8283.
22. Yu, X., Ding, Q., Chen, Z., Wu, J. Tetrahedron Lett. 2009, 50, 4279.
23. Moonen, K., Van Meenen, E., Verwee, A., Stevens, C.V. Angew. Chem. Int. Ed. 2005, 44, 7407.
24. Lewkowsi, J. Focus on Organometallic Chemistry Research; Nova Science Publishers, Inc., 2005.
25. Ordonez, M., Rojas-Cabrera, H., Cativiela, C. Tetrahedron (Report 856) 2009, 65, 17.
26. Bhadury, P.S., Song, B.-A., Yang, S., Zhang, Y., Zhang, S. Curr. Org. Synth. 2008, 5, 134.
27. Hosseini-Sarvari, M. Tetrahedron 2008, 64, 5459.
28. Amedjkouh, M., Westerlund, K. Tetrahedron Lett. 2004, 45, 5175.
29. Lecercle, D., Gabillet, S., Goinis, J.-M., Taran, F. Tetrahedron Lett. 2008, 49, 2083.
30. Baraldi, P.G., Gaurneri, M., Moroder, F., Pollini, G.P. Synthesis 1982, 653.
31. Hanessian, S., Guesne, S., Riber, L., Marin, J., Benoist, A., Mennecier, P., Rupin, A., Verbeuren, J.J., De Nanteuil, G. Bioorg. Med. Chem. Lett. 2008, 18, 1058.
32. Ryglowski, A., Kafarski, P. Tetrahedron 1996, 52, 10685.
33. Kassaee, M.Z., Movahedi, F., Masrouri, H. Synlett 2009, 1326.
34. Beck, J., Gharbi, S., Herteg-Fernea, A., Vercheval, L., Bebrone, C., Lassaux, P., Zervosen, A., Marchand-Brynaert, J. Eur. J. Org. Chem. 2009, 85.
35. Baslé, O., Li, C.-J. Chem. Commun. 2009, 4124.
36. Palacios, F., Alonso, C., de los Santos, J. Chem. Rev. 2005, 105, 899.
37. Juaristi, A., Soloshonok, V. Enantioselective Synthesis of Beta-Aminoacids; John Wiley & Sons, Ltd, 2005.
38. Janecki, T., Kedzia, J., Wasek, T. Synthesis 2009, 1227.
39. Enders, D., Saint-Dizier, A., Lannou, M., Lenzen, A. Eur. J. Org. Chem. 2005, 29.
40. Stevens, C.V., Gallant, M., De Kimpe, N. Tetrahedron Lett. 1999, 40, 3457.
41. Vanderhoydonck, B., Stevens, C.V. Synthesis 2004, 722.
42. Vanderhoydonck, B., Stevens, C.V. J. Org. Chem. 2005, 70, 191.
43. Vanderhoydonck, B., Stevens, C.V. Tetrahedron 2007, 63, 7679.
44. Whitesell, M.A., Kyba, E.P. Tetrahedron Lett. 1984, 25, 2119.
45. Palacios, F., Aparicio, D., Garcia, J., Rodriguez, E. Eur. J. Org. Chem. 1998, 1413.
46. Palacios, F., Vicario, J., Maliszewska, A., Aparicio, D. J. Org. Chem. 2007, 72, 2682.
47. Vicario, J., Aparicio, D., Palacios, F.D. J. Org. Chem. 2009, 74, 452.
48. Marchand-Brynaert, J., Defacqz, N., Robiette, R. Recent Res. Devel. Org. Chem. 2001, 5, 207.
49. Robiette, R., Defacqz, N., Peeters, D., Marchand-Brynaert, J. Curr. Org. Synth. 2005, 2, 175.
50. Fringuelli, F., Taticchi, A. The Diels-Alder Reaction; John Wiley & Sons, Ltd, 2002.
51. Garcia, J., Mayoral, J., Salvatella, L. Eur. J. Org. Chem. 2004, 85.
52. Bansal, R.K., Gupta, N., Kumawat, S.K., Dixit, G. Tetrahedron 2008, 64, 6395.
53. Evans, D.A., Chapman, K.T., Bisaha, J. J. Am. Chem. Soc. 1988, 10, 1238.
54. Carmona, D., Lamata, M.P., Viguri, F., Rodriguez, R., Lahoz, F.J., Dobrinovitch, I.T., Oro, L.A. Dalton Trans. 2008, 3328.
55. Akalay, D., Duerner, G., Goebel, M.W. Eur. J. Org. Chem. 2008, 2365.
56. Gouverneur, V., Reiter, M. Chem.-Eur. J. 2005, 11, 5806.
57. Headley, A.D., Ni, B. Aldrichimica Acta 2007, 40, 107.
58. Mc Clure, C.K., Hansen, K.B. Tetrahedron Lett. 1996, 37, 2149.
59. Daniewski, W., Griffin, C. J. Org. Chem. 1966, 31, 3236.
60. Defacqz, N., Touillaux, R., Tinant, B., Declercq, J.-P., Peeters, D., Marchand-Brynaert, J. J. Chem. Soc., Perkin Trans. 2 1997, 1965.
61. Defacqz, N., Touillaux, R., Marchand-Brynaert, J. J. Chem. Res. 1998, 512.
62. Defacqz, N., Cordi, A., Marchand-Brynaert, J. J. Chem. Soc., Perkin Trans. 1 2001, 2632.
63. Robiette, R., Marchand-Brynaert, J. J. Chem. Soc., Perkin Trans. 2 2001, 2155.
64. Robiette, R., Defacqz, N., Stofferis, J., Marchand-Brynaert, J. Tetrahedron 2003, 59, 4167.
65. Robiette, R., Cheboub-Benchaba, K., Peeters, D., Marchand-Brynaert, J. J. Org. Chem. 2003, 68, 9809.
66. Monbaliu, J.-C., Robiette, R., Peeters, D., Marchand-Brynaert, J. Tetrahedron Lett. 2009, 50, 1314.
67. Monbaliu, J.-C., Tinant, B., Marchand-Brynaert, J. J. Mol. Structure 2008, 879, 113.
68. Monbaliu, J.-C., Tinant, B., Marchand-Brynaert, J. Heterocycles 2008, 75, 2459.
69. Pudovik, N.A., Konovalova, I.V., Ishmaeva, E.A. J. General Chemistry USSR 1963, 33, 2446.
70. Griffin, C.E., Daniewski, W.M. J. Org. Chem. 1970, 35, 1691.
71. Darling, S.D., Subramanian, N. J. Org. Chem. 1975, 40, 2851.
72. Yamana, K., Nakano, H. Tetrahedron Lett. 1996, 37, 5963.
73. Yamana, K., Ibatan, T., Nakano, H. Synthesis 2006, 4124.
74. Cooper, D., Trippett, S. J. Chem. Soc., Perkin Trans. 1 1981, 2127.
75. Heydt, H., BergShässer, V., Fässler, R., Fuchs, E., Kamel, N., Machewitz, T., Michels, G., Rösch, W., Regitz, M., Mazerolles, P., Laurent, C., Farcher, A. Bull. Soc. Chim. Fr. 1995, 132, 652.
76. Wyatt, P., Villalonga-Barber, C., Motevalli, M. Tetrahedron Lett. 1999, 40, 149.
77. Zgani, I., Menut, C., Sema, M., Gallois, V., Laffont, V., Liartard, J., Liartard, J.-P., Criton, M., Montero, J.-L. J. Med. Chem. 2004, 47, 4600.
78. Ruiz, M., Ojea, V., Conde, S., Quintela, J.-M. Synlett 2003, 5, 689.
79. Darling, S.D., Muralidharan, F.N., Muralidharan, V.B. Tetrahedron Lett. 1979, 30, 2757.
80. Kosolapoff, G.M. Izvest. Akad. Nauk. S.S.S.R. 1956, 923.
81. Pudovik, A.N., Ishmaeva, E.A. Zhurnal Organicheskoi Khimii 1968, 38, 197.
82. Lavielle, G., Strutz, G., Normant, H. Bull. Soc. Chem. Fr. 1976, 1369.
83. Gurevich, I.E., Tebby, J.-C. J. Chem. Soc., Perkin Trans. 1 1995, 10, 1259.
84. Gurevich, I.E., Dogadina, A.V., Ionin, B.I., Petrov. A.A. Zhurnal Organicheskoi Khimii 1993, 63, 311, and previous papers.
85. Christov, V.C. Phosphorus, Sulfur Silicon Relat. Elem. 1998, 32, 73.
86. Christov, V.C. Phosphorus, Sulfur Silicon Relat. Elem. 1998, 32, 79.
87. Villemin, E., Elias, B., Marchand-Brynaert, J. unpublished results.
88. Gurevich, I.E., Dogadina, A.V., Ionin, B.I., Petrov, A.A. Russ. J. Gen. Chem. 1991, 61, 1967.
89. Al Badri, H., About-Joudet, E., Collignon, N. Tetrahedron Lett. 1996, 37, 2951.
90. Okauchi, T., Yano, T., Furkamachi, T., Ichikavwa, J., Minami, T. Tetrahedron Lett. 1983, 40, 5337.
91. Al Quntar, A.A., Srebnik, M. Org. Lett. 2001, 3, 1379.
92. Timmer, M.S.M., Ovaa, H., Filippov, D.V., van der Marel, G.A., van Boom, J.H. Tetrahedron Lett. 2001, 42, 8231.
93. Al-Badri, H., About-Joudé, E., Collignon, N. Synthesis 1994, 1072.
94. Han, L.-B., Ono, Y., Yazawa, H. Org. Lett. 2005, 7, 2909.
95. Kobayashi, Y., William, A.D. Org. Lett. 2002, 4, 4241.
96. Pudovick, A.N., Aladzheva, I.M. Zhurnal Organicheskoi Khimii 1963, 33, 708.
97. Brel', V.K., Komarov, V.Y., Ionin, B.I., Petrov, A.A. Zhurnal Organicheskoi Khimii 1989, 59, 2843.
98. Pudovik, A.N., Konovalova, I.V. J. Gen. Chem. USSR 1961, 31, 1580.
99. Kosolapoff, G.M. J. Am. Chem. Soc. 1948, 70, 1974.
100. Monbaliu, J.-C., Marchand-Brynaert, J. Tetrahedron Lett. 2008, 49, 1839.
101. Monbaliu, J.-C., Marchand-Brynaert, J. Synthesis 2009, 1876.
102. Villemin, E., Herent, M.-F., Habib Jiwan, J.-L., Elias, B., Marchand-Brynaert, J. Tetrahedron Lett., submitted manuscript.
103. Clement, R.A. J. Org. Chem. 1962, 27, 1115.
104. Gorenstein, D.G. Phosphorus-31 NMR, Principles and Applications; Academic Press Inc., 1984.
105. Quin, L.S. A Guide to Organophosphorus Chemistry; John Wiley & Sons Inc., 2000.
106. Tinant, B., Defacqz, N., Robiette, R., Touillaux, R., Marchand-Brynaert, J. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 389.
107. Tietze, L., Kettschau, G. Stereoselective Heterocyclic Synthesis I 1997, 189, 1.
108. Isawa, S., Fakhruddin, A., Nishiyama, H. Mini-Rev. Org. Chem. 2005, 2, 157.
109. Lee, J., Chen, L., West, A., Richter-Addo, G. Chem. Rev. 2002, 102, 1019.
110. Glaser, R., Murmann, R., Barnes, C. J. Org. Chem. 1996, 61, 1047.
111. Quadrelli, P., Mella, M., Invernizzi, A., Caramella, P. Tetrahedron 1999, 55, 10497.
112. Christie, C., Kirby, G., McGuigan, H., Mackinnon, J. J. Chem. Soc., Perkin Trans. 1 1985, 2469.
113. Boger, D., Patel, M., Takusagawa, F. J. Org. Chem. 1985, 50, 1911.
114. Monbaliu, J.-C., Cukalovic, A., Marchand-Brynaert, J., Stevens, C.V. Tetrahedron Lett. 2010, 51, 5830.
115. Monbaliu, J.-C., Tinant, B., Marchand-Brynaert, J. J. Org. Chem. 2010, 75, 5478.
116. Nitsch, H., Kresze, G. Angew. Chem. Int. Ed. 1976, 15, 760.
117. Defoin, A., Joubert, M., Heuchel, J., Strehler, C., Streith, J. Synthesis 2000, 1719.
118. Riddell, F., Labaziewicz, H. J. Chem. Soc., Perkin Trans. 1 1979, 2926.
119. Sha, X., Isbell, T.S., Patel, R.P., Day, C.S., King, S.B. J. Am. Chem. Soc. 2006, 128, 9687.
120. Keck, G., Webb, R., Yates, J. Tetrahedron 1981, 37, 4007.
121. Wijnen, J., Engberts, J. J. Org. Chem. 1997, 62, 2039.
122. Mulvihill, M., Gage, J., Miller, M. J. Org. Chem. 1998, 63, 3357.
123. Monbaliu, J.-C., Marchand-Brynaert, J., Peeters, D. Tetrahedron Lett. 2009, 50, 2555.
124. McClure, C.K., Grote, C.W. Tetrahedron Lett. 1991, 32, 5313.
125. Gouverneur, V., Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363.
126. Yamamoto, H., Kawasaki, M. Bull. Soc. Chim. Jpn 2007, 80, 595.
127. Molt, O., Schrader, T. Synthesis 2002, 2633.
128. Monbaliu, J.-C., Tinant, B., Peeters, D., Marchand-Brynaert, J. Tetrahedron Lett. 2010, 51, 1052.
129. Bennani, Y., Hanessian, S. Tetrahedron 1996, 52, 13837.
130. Hansch, C., Leo, A., Taft, R.W. Chem. Rev. 1991, 91, 165.
131. Sainz-Diaz, C.I., Hernandez-Laguna, A., Smeyers, N.J., Smeyers, Y.G. J. Mol. Struct. 1995, 330, 231.
132. Janecki, T. In Target in Heterocyclic Systems; Attanasi, O.A., Spinelli, D., Eds., Società Chimica Italiana: Rome, 2006; Vol. 10, p. 301.
133. Leyssens, T., Peeters, D. J. Org. Chem. 2008, 73, 2725.
134. Leyssens, T., Peeters, D. Tetrahedron Lett. 2008, 49, 2095.
135. Leyssens, T., Peeters, D. J. Mol. Struct. 2004, 673, 79.
136. Leyssens, T., Peeters, D. J. Mol. Struct. 2004, 686, 71.
137. Robiette, R., Marchand-Brynaert, J., Peeters, D. J. Mol. Struct. 2002, 587, 159.
138. Sulzer-Moss, S., Alexakis, A., Mareda, J., Bollot, G., Bernardinelli, G., Filinchuk, Y. Chem.-Eur. J. 2009, 15, 3204.
139. Dembitsky, V.M., Al Quntar, A.A., Haj-Yehia, A., Srebnik, M. Mini Rev. Org. Chem. 2005, 2, 91.
140. Minami, T., Motoyoshiya, J. Synthesis 1992, 333.
141. Leach, G.L., Houk, K.N. J. Org. Chem. 2001, 66, 5192.
142. Monbaliu, J.-C., Dive, G., Marchand-Brynaert, J., Peeters, D. J. Mol. Struct.: Theochem. 2010, 959, 49.
143. Domingo, L.R., Sàez, J.A. Org. Biomol. Chem. 2009, 7, 3576, and previous publications.
144. McKenna, C.E., Higa, M.T., Cheung, N.H., McKenna, M.-C. Tetrahedron Lett. 1977, 18, 155.
145. Stephan, E., Brossat, M., Lecomte, V., Bouit, P. Tetrahedron 2006, 62, 3052.
146. Adams, L., Charmant, J., Cox, R., Walter, M., Whittingham, W. Org. Biomol. Chem. 2004, 2, 542.
147. Devedjiev, I.T., Bairyamov, S.G., Videva, V.S. Heteroat. Chem. 2008, 19, 252.
148. Tang, M., Pyne, S.G. J. Org. Chem. 2003, 68, 7818.
149. Wroblewski, A., Glowacka, I. Tetrahedron 2005, 61, 11930.
150. Falentin, C., Beaupere, D., Demailly, G., Stasik, I. Carbohydr. Res. 2007, 342, 2807.
151. Wroblewski, A.E., Bak-Sypien, I.I. Tetrahedron: Asymmetry 2007, 18, 2218.
152. Hwang, J.-M., Jung, K.-Y. Bull. Korean Chem. Soc. 2002, 23, 1841.
153. Fredenhagen, A., Angst, C., Peter, H.H. J. Antibiot. 1995, 48, 1043.
154. Berkowitz, D., Charette, B., Karukurichi, K., McFadden, J. Tetrahedron: Asymmetry 2006, 17, 869.
155. Rao, H., Jin, Y., Fu, H., Jiang, Y., Zhao, Y. Chem.-Eur. J. 2006, 12, 3636.
156. Ciufolini, M.A., Xi, N. Chem. Soc. Rev. 1998, 27, 437.
157. Sivertsen, A.C., Gasior, M., Bjerring, M., Hansen, S.U., Lopez, O.L., Nielsen, N.C., Bols, M. Eur. J. Org. Chem. 2007, 1735.