Synthesis of a chiral C2-symmetric sterically hindered pyrrolidine nitroxide radical via combined iterative nucleophilic additions and intramolecular 1,3-dipolar cycloadditions to cyclic nitrones

Journal of Organic Chemistry

Volumn 77, Issue 23, 2012, Pages 10688-10698

  Morozov, Denis A ^a,b   Kirilyuk, Igor A ^a   Komarov, Denis A ^a   Goti, Andrea ^c   Bagryanskaya, Irina Yu ^a   Kuratieva, Natalia V ^d   Grigorev, Igor A ^a  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

^c UNIVERSITY OF FLORENCE   (Italy)

^d NIKOLAEV INSTITUTE OF INORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DIPOLAR CYCLOADDITIONS; CARBON ATOMS; CYCLIC NITRONES; HIGH STABILITY; INTRAMOLECULAR CYCLOADDITION REACTIONS; METHYLENE GROUPS; NITRONES; NITROXIDE RADICALS; NITROXIDES; NUCLEOPHILIC ADDITIONS; PYRROLIDINES; QUATERNIZATION; STEREO-SELECTIVE;

CYCLOADDITION; ORGANOMETALLICS; REACTION INTERMEDIATES;

ITERATIVE METHODS;

ASCORBIC ACID; CARBON; NITRONE DERIVATIVE; NITROXIDE DERIVATIVE; NUCLEOPHILE; ORGANOMETALLIC COMPOUND; PYRROLIDINE DERIVATIVE; TARTARIC ACID;

ARTICLE; ATOM; CYCLOADDITION; DRUG SYNTHESIS; MOLECULAR INTERACTION; OXIDATION; STEREOCHEMISTRY;

EID: 84870943523     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3019158     Document Type: Article

References (107)

1. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688
2. Iwamura, H.; Inoue, K. Magnetic Ordering in Metal Coordination Complexes with Aminoxyl Radicals. In Magnetism: Molecules and materials II. Molecule-Based Materials; Miller, J. S.; Drillion, M., Eds.; Wiley-VCH Verlag GmbH & Co KGaA: Weinheim, 2001; pp 61-108.
3. Ovcharenko, V. Metala-Nitroxide Complexes: Synthesis and Magnetostructural Correlations. In Stable Radicals. Fundamentals and Applied Aspects of Odd-Electron Compounds; Hicks, R. G., Ed.; Wiley: New York, 2010; pp 461-506.
4. de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153-1174
5. Bobbitt, J. M.; Brückner, C.; Merbouh, N. Org. React. 2009, 74, 106-424
6. Vogler, T.; Studer, A. Synthesis 2008, 1979-1993
7. Halpern, H. J.; Yu, C.; Peric, M.; Barth, E.; Grdina, D. J.; Teicher, B. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13047-13051
8. Khramtsov., V. V.; Volodarsky, L. B. Biological Magnetic Resonance, Vol. 14: Spin Labeling: The Next Millennium; Plenum Press: New York, London, 1998.
9. Khramtsov, V. V.; Grigorev, I. A.; Foster, M. A.; Lurie, D. J.; Nicholson, I. Cell. Mol. Biol. 2000, 46, 1361-1374
10. Khramtsov, V. V.; Grigorev, I. A.; Foster, M. A.; Lurie, D. J. Antioxid. Redox Signaling 2004, 6, 667-676
11. Ahn, H.-Y.; Fairful-Smith, K. E.; Morrow, B. J.; Lussini, V.; Kim, B.; Bondar, M. V.; Bottle, S. E.; Belfield, K. D. J. Am. Chem. Soc. 2012, 134, 4721-4730
12. Berliner, L. J. Biological Magnetic Resonance, Vol. 14: Spin Labeling: The Next Millennium; Plenum Press: New York, London, 1998.
13. Soule, B. P.; Hyodo, F.; Matsumoto, K.-I.; Simone, N. L.; Cook, J. A.; Krishna, M. C.; Mitchell, J. B. Free Radic. Biol. Med. 2007, 42, 1632-1650
14. Keana, J. F. W.; Pow, S.; Rosen, G. M. Magn. Reson. Med. 1987, 3, 83-88
15. Winalski, C. S.; Shortkroff, S.; Mulkern, R. V.; Schneider, E.; Rosen, G. M. Magn. Reson. Med. 2002, 48, 965-972
16. Suga, T.; Nishide, H. Rechargeable Batteries Using Robust but Redox Active Organic Radicals. In Stable Radicals. Fundamentals and Applied Aspects of Odd-Electron Compounds; Hicks, R. G., Ed.; Wiley: New York, 2010; pp 507-520.
17. Wetter, Ch.; Gierlich, J.; Knoop, Ch. A.; Müller, Ch.; Schulte, T.; Studer, A. Chem.î-̧Eur. J. 2004, 10, 1156-1166
18. Miura, Y.; Nakamura, N.; Taniguchi, I. Macromolecules 2001, 34, 447-455
19. Marx, L.; Chiarelli, R.; Guiberteau, T.; Rassat, A. J. Chem. Soc., Perkin Trans. 1 2000, 1181-1182
20. Kirilyuk, I. A.; Bobko, A. A.; Grigorev, I. A.; Khramtsov, V. V. Org. Biomol. Chem. 2004, 2, 1025-1030
21. Kinoshita, Yu.; Yamada, K.; Yamasaki, T.; Sadsue, H.; Sakai, K.; Utsumi, H. Free Radic. Res. 2009, 43, 565-571
22. Yamasaki, T.; Mito, F.; Ito, Y.; Pandian, S.; Kinoshita, Y.; Nakano, K.; Murugesan, R.; Sakai, K.; Utsumi, H.; Yamada, K. J. Org. Chem. 2011, 76, 435-440
23. Rajca, A.; Kathirvelu, V.; Roy, S. K.; Pink, M.; Rajca, S.; Sarkar, S.; Eaton, S. S.; Eaton, G. R. Chem.î-̧Eur. J. 2010, 16, 5778-5782
24. Yoshioka, T.; Higashida, S.; Murayama, K. Bull. Chem. Soc. Jpn. 1972, 45, 636-638
25. Smythe, M. L.; Nakaie, C. R.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 10555-10562
26. Schulte, T.; Siegenthaler, K. O.; Luftmann, H.; Letzel, M.; Studer, A. Macromolecules 2005, 38, 6833-6840
27. Sakai, K.; Yamada, K. I.; Yamasaki, T.; Kinoshita, Y.; Mito, F.; Utsumi, H. Tetrahedron 2010, 66, 2311-2315
28. Yoshioka, T.; Mori, E.; Murayama, K. Bull. Chem. Soc. Jpn. 1972, 45, 1855-1860
29. Lai, J. T. Synthesis 1981, 40-42
30. Marx, L.; Rassat, A. Angew. Chem., Int. Ed. 2000, 39, 4494-4496
31. Fairfull-Smith, K. E.; Brackmann, F.; Bottle, S. E. Eur. J. Org. Chem. 2009, 1902-1915
32. Braslau, R.; Burill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron: Asymmetry 1997, 8, 3209-3212
33. Morat, C.; Rassat, A. Tetrahedron Lett. 1979, 19, 4561-4564
34. Toda, T.; Morimura, S.; Murayama, K. Bull. Chem. Soc. Jpn. 1972, 45, 557-561
35. Reznikov, V. A.; Volodarsky, L. B. Tetrahedron 1993, 49, 10669-10692
36. Keana, J. F. W. Synthesis and Chemistry of Nitroxide Spin Labels. In Spin Labeling in Pharmacology; Holtzman, J. L., Ed.; Academic Press: Orlando, 1984; pp 1-85.
37. Keana, J. F. W.; Lee, T. D.; Bernard, E. M. J. Am. Chem. Soc. 1976, 98, 3052-3053
38. Lee, T. D.; Birrell, G. B.; Keana, J. F. W. J. Am. Chem. Soc. 1978, 100, 1618-1619
39. Keana, J. F. W.; Seyedrezai, S. E.; Gaughan, J. J. Org. Chem. 1983, 48, 2644-2647
40. Keana, J. F. W.; Cuomo, J.; Lex, L.; Seyedrezai, S. E. J. Org. Chem. 1983, 48, 2647-2654
41. Keana, J. F. W.; Prabhu, V. S. J. Org. Chem. 1986, 51, 4300-4301
42. Benfaremo, N.; Steenbock, M.; Klapper, M.; Müllen, K.; Enkelmann, V.; Cabrera, K. Liebigs Ann. 1996, 1413-1415
43. Baracz, N. M.; Hankovsky, O. H.; Sár, C. P.; Jerkovich, G.; Hideg, K. Synthesis 1996, 204-208
44. Haire, D. L.; Janzen, E. G.; Chen, G.; Robinson, V. J.; Hrvoic, I. Magn. Reson. Chem. 1999, 37, 251-258
45. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Gautier-Luneau, I.; Pierre, J. L. J. Org. Chem. 1997, 62, 9385-9388
46. Shibata, T.; Uemae, K.; Yamamoto, Y. Tetrahedron: Asymmetry 2000, 11, 2339-2346
47. Merino, P. In Science of Synthesis; Padwa, A., Ed.; Thieme: Stuttgart, 2004; Vol. 27, pp 511-580.
48. Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 2, pp 83-168.
49. Frederickson, M. Tetrahedron 1997, 53, 403-425
50. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863-909
51. Jones, R. C. F.; Martin, J. N. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; John Wiley & Sons: New York, 2002; The Chemistry of Heterocyclic Compounds Vol. 59, pp 1-81.
52. Grigorev, I. A. Nitrones: Novel Strategies in Synthesis. In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis. Novel Strategies in Synthesis; Feuer, H., Ed.; Wiley: New York, 2008; pp 129-434.
53. Sár, C. P.; OÌsz, E.; JekoÌ, J.; Hideg, K. Synthesis 2005, 255-259
54. Morozov, D. A.; Kirilyuk, I. A.; Gatilov, Yu. V.; Bagryanskaya, I. Yu.; Bozhko, J. Yu.; Komarov, D. A.; Grigorev, I. A. Synthesis 2009, 343-348
55. Cicchi, S.; HoÌld, I.; Brandi, A. J. Org. Chem. 1993, 58, 5274-5275
56. Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761-763
57. Cardona, F.; Goti, A.; Picasso, S.; Vogel, P.; Brandi, A. J. Carbohydr. Chem. 2000, 19, 585-601
58. Goti, A.; Cicchi, S.; Mannucci, V.; Cardona, F.; Guarna, F.; Merino, P.; Tejero, T. Org. Lett. 2003, 5, 4235-4238
59. Merino, P.; Tejero, T.; Revuelta, J.; Romero, P.; Cicchi, S.; Mannucci, V.; Brandi, A.; Goti, A. Tetrahedron: Asymmetry 2003, 14, 367-379
60. Marradi, M.; Cicchi, S.; Delso, J. I.; Rosi, L.; Tejero, T.; Merino, P.; Goti, A. Tetrahedron Lett. 2005, 46, 1287-1290
61. Cardona, F.; Moreno, G.; Guarna, F.; Vogel, P.; Schuetz, C.; Merino, P.; Goti, A. J. Org. Chem. 2005, 70, 6552-6555
62. Delso, I.; Marca, E.; Mannucci, V.; Tejero, T.; Goti, A.; Merino, P. Chem.î-̧Eur. J. 2010, 16, 9910-9919
63. LeBel, N. A.; Spurlock, L. A. J. Org. Chem. 1964, 29, 1337-1339
64. LeBel, N. A.; Post, M. E.; Hwang, D. J. Org. Chem. 1979, 44, 1819-1823
65. Tufariello, J. J.; Mullen, G. B.; Tegeler, J. J.; Trybulski, E. J.; Wong, S. C.; Ali, Sk. A. J. Am. Chem. Soc. 1979, 101, 2435-2442
66. Iwamoto, O.; Sekine, M.; Koshino, H.; Nagasawa, K. Heterocycles 2006, 70, 107-112
67. Ali, Sk. A.; Wazeer, M. I. M. Tetrahedron 1993, 49, 4339-4354
68. Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1863-1864
69. Nagasawa, K.; Georgieva, A.; Nakata, T. Tetrahedron 2000, 56, 187-192
70. Cardona, F.; Faggi, E.; Liguori, F.; Cacciarini, M.; Goti, A. Tetrahedron Lett. 2003, 44, 2315-2318
71. Liautard, V.; Christina, A. E.; Desvergnes, V.; Martin, O. R. J. Org. Chem. 2006, 71, 7337-7345
72. Cardona, F.; Parmeggiani, C.; Faggi, E.; Bonaccini, C.; Gratteri, P.; Sim, L.; Gloster, T. M.; Roberts, S.; Davies, G. J.; Rose, D. R.; Goti, A. Chem.î-̧Eur. J. 2009, 15, 1627-1636
73. Bonaccini, C.; Chioccioli, M.; Parmeggiani, C.; Cardona, F.; Lo, Re, D.; Soldaini, G.; Vogel, P.; Bello, C.; Goti, A.; Gratteri, P. Eur. J. Org. Chem. 2010, 5574-5585
74. Carmona, A. T.; Whigtman, R. H.; Robina, I.; Vogel, P. Helv. Chim. Acta 2003, 86, 3066-3073
75. Coutouli-Argyropoulou, E.; Xatzis, Ch.; Argyropoulos, N. Nucleosides, Nucleotides Nucleic Acids 2008, 27, 84-100
76. Podolan, G.; KlesÌcÌíková, L.; FisÌera, L.; KozÌísÌek, J.; Fronc, M. Synlett 2011, 1668-1672
77. Goti, A.; Cacciarini, M.; Cardona, F.; Cordero, F. M.; Brandi, A. Org. Lett. 2001, 3, 1367-1369
78. Merino, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776-782
79. Gössinger, E.; Imhof, R.; Wehrli, H. Helv. Chim. Acta 1975, 58, 96-103
80. Yang, S.-H.; Clark, G. R.; Caprio, V. Org. Biomol. Chem. 2009, 7, 2981-2990
81. Merino, P.; Delso, I.; Tejero, T.; Cardona, F.; Goti, A. Synlett 2007, 2651-2654
82. Merino, P.; Delso, I.; Tejero, T.; Cardona, F.; Marradi, M.; Faggi, E.; Parmeggiani, C.; Goti, A. Eur. J. Org. Chem. 2008, 2929-2947
83. Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem. 1995, 60, 4743-4748
84. Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem. 1997, 62, 3119-3125
85. Goti, A.; Cicchi, S.; Cordero, F. M.; Fedi, V.; Brandi, A. Molecules 1999, 4, 1-12
86. Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: New York, 1988.
87. Cicchi, S.; Marradi, M.; Goti, A.; Brandi, A. Tetrahedron Lett. 2001, 42, 6503-6505
88. Brandi, A.; Cardona, F.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem.î-̧Eur. J. 2009, 15, 7808-7821
89. Grigg, R.; Markandu, J.; Surendrakumar, S.; Thornton-Pett, M.; Warnock, W. J. Tetrahedron 1992, 48, 10399-10432
90. Dondas, H. A.; Grigg, R.; Hadjisoteriou, M.; Markandu, J.; Thomas, W. A.; Kennewell, P. Tetrahedron 2000, 56, 10087-10096
91. Holmes, A. B.; Hughes, A. B.; Smith, A. L. Synlett 1991, 1, 47-48
92. Huisgen, R.; Grashey, R.; Hauck, H.; Seidl, H. Chem. Ber. 1968, 101, 2043-2055
93. LeBel, N. A.; Ojha, N. D.; Menke, J. R.; Newland, R. J. J. Org. Chem. 1972, 37, 2896-2898
94. Bapat, J. B.; Black, D. St. C.; Brown, R. F. C.; Ichlov, C. Aust. J. Chem. 1972, 25, 2445-2450
95. Vasella, A.; Voeffray, R. Helv. Chim. Acta 1982, 65, 1134-1144
96. Koizumi, T.; Hirai, H.; Yoshii, E. J. Org. Chem. 1982, 47, 4004-4005
97. Tice, C. M.; Ganem, B. J. Org. Chem. 1983, 48, 5048-5050
98. DeShong, P.; Leginus, J. M. J. Am. Chem. Soc. 1983, 105, 1686-1688
99. Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron 1985, 41, 3455-3462
100. Iida, H.; Kasahara, K.; Kibayashi, C. J. Am. Chem. Soc. 1986, 108, 4647-4648
101. Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; De Sarlo, F. Tetrahedron Lett. 1990, 31, 3351-3354
102. Zhang, D.; Süling, C.; Miller, M. J. J. Org. Chem. 1998, 63, 885-888
103. Revuelta, J.; Cicchi, S.; Brandi, A. Tetrahedron Lett. 2004, 45, 8375-8377
104. Murahashi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736-1744
105. Okazaki, Sh.; Mannan, M. A.; Sawai, K.; Masumizu, T.; Miura, Y.; Takeshita, K. Free Radic. Res. 2007, 41, 1069-1077
106. Bobko, A. A.; Kirilyuk, I. A.; Gritsan, N. P.; Polovyanenko, D. N.; Grigorev, I. A.; Khramtsov, V. V.; Bagryanskaya, E. G. Appl. Magn. Reson. 2010, 39, 437-451
107. Bobko, A. A.; Kirilyuk, I. A.; Grigorev, I. A.; Zweier, J. L.; Khramtsov, V. V. Free Radic. Biol. Med. 2007, 42, 404-412