none 10.3987/COM-08-11396 CLOCKSS Archive CLOCKSS Archive 5187 36255934 73640 20090216111438 10.13030 2024-06-24T20:35:08Z 2009-02-16T02:15:56Z 7 HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2008 75 9 Patrice Vanelle R士i Szabo Maxime D. Crozet Patrice Vanelle 2008 2263 COM-08-11396 10.3987/COM-08-11396 20090216111438 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-08-11396 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-08-11396 10.1246/bcsj.78.154 1. J.-Y. Kazock, C. Enguehard-Gueiffier, I. Théry, and A. Gueiffier, Bull. Chem. Soc. Jpn., 2005, 78, 154. 10.1002/cber.19901230218 2. H.-J. Knoelker, R. Boese, and R. Hitzemann, Chem. Ber., 1990, 123, 327. 3. J. J. Kaminski, J. A. Bristol, C. Puchalski, R. G. Lovey, A. J. Elliot, H. Guzik, D. M. Solomon, D. J. Conn, M. S. Domalski, S.-C. Wong, E. H. Gold, J. F. Long, P. J. S. Chiu, M. Steinberg, and A. T. McPhail, J. Med. Chem., 1985, 28, 876; J. J. Kaminsky and A. M. Doweyko, J. Med. Chem., 1997, 40, 427; K. Munson, R. Garcia, and G. Sachs, Biochemistry, 2005, 44, 5267. 4. P. Sanfilippo, M. Urbanski, J. B. Press, B. Dubinsky, and J. B. Moore, Jr., J. Med. Chem., 1988, 31, 2221. 10.1021/jm9507901 5. A. Gueiffier, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, A. Kerbal, E. M. Essassi, J.-C. Debouzy, M. Witvrouw, Y. Blache, J. Balzarini, E. De Clercq, and J.-P. Chapat, J. Med. Chem., 1996, 39, 2856; A. Gueiffier, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, M. Witvrouw, J. Balzarini, E. De Clercq, and J.-P. Chapat, J. Med. Chem., 1998, 41, 5108; M. Lhassani, O. Chavignon, J.-M. Chezal, J.-C. Teulade, J.-P. Chapat, R. Snoeck, G. Andrei, J. Balzarini, E. De Clercq, and A. Gueiffier, Eur. J. Med. Chem., 1999, 34, 271. 6. G. Allen and P. George, Fr. Demande FR 2599368, 1987 (Chem. Abstr., 1987, 109, 170422); J. Allen and P. George, Fr. Demande FR 2612928, 1988 (Chem. Abstr., 1988, 111, 174090); J. Allen and P. George, Fr. Demande FR 2606411, 1988 (Chem. Abstr., 1988, 110, 57665); P. George and C. Giron, Eur. Pat. Appl. EP 172096, 1986 (Chem. Abstr., 1986, 105, 97458); J.-P. Kaplan and P. George, Eur. Patent 0050563, 1982 (Chem. Abstr., 1982, 97, 149531). 7. P. George, J. Allen, and G. Jaurand, Fr. Demande FR 2612927, 1988 (Chem. Abstr., 1988, 111, 115178). 10.1021/jm051065l 8. S. C. Goodacre, L. J. Street, D. J. Hallett, J. M. Crawforth, S. Kelly, A. P. Owens, W. P. Blackaby, R. T. Lewis, J. Stanley, A. J. Smith, P. Ferris, B. Sohal, S. M. Cook, A. Pike, N. Brown, K. A. Wafford, G. Marshall, J. L. Castro, and J. R. Atack, J. Med. Chem., 2006, 49, 35; J.-P. Kaplan and P. George, Eur. Pat. Appl. EP 92458, 1983 (Chem. Abstr., 1983, 100, 103345); J.-P. Kaplan, P. George, and J.-M. Bernardon, Eur. Pat. Appl. EP 92459, 1983 (Chem. Abstr., 1983, 100, 139102). 9. P. George and J. Allen, Eur. Patent EP 267111, 1988 (Chem. Abstr., 1988, 109, 149531). 10. ‘Electron Transfer Reactions in Organic Synthesis,’ ed. by P. Vanelle, Research Signpost, Trivandrum, 2002. 10.1021/cr960134o 11. For recent review, see: R. A. Rossi, A. B. Pierini, and A. B. Peñeñory, Chem. Rev., 2003, 103, 71. 12. P. Vanelle, N. Madadi, C. Roubaud, J. Maldonado, and M. P. Crozet, Tetrahedron, 1991, 47, 5173. 10.3998/ark.5550190.0004.a26 13. M. D. Crozet, C. Castera, M. Kaafarani, M. P. Crozet, and P. Vanelle, Arkivoc, 2003, X, 273. 10.3987/COM-04-10285 14. C. Castera, M. D. Crozet, M. P. Crozet, and P. Vanelle, Heterocycles, 2005, 65, 337. 10.1055/s-2006-942505 15. C. Castera-Ducros, M. D. Crozet, and P. Vanelle, Synthesis, 2006, 2777. 10.1055/s-2007-990905 16. R. Szabo, M. D. Crozet, and P. Vanelle, Synthesis, 2008, 127. 17. N. Kornblum, S. D. Boyd, and N. Ono, J. Am. Chem. Soc., 1974, 96, 2580. 18. M. P. Moon and J. W. Wolfe, J. Org. Chem., 1979, 44, 4081. 10.1002/anie.198200013 19. M. Chanon and M. L. Tobe, Angew. Chem., Int. Ed. Engl., 1982, 21, 1. 20. W. R. Bowman, ‘Photoinduced Electron Transfer: Photoinduced Nucleophilic Substitution at sp3-Carbon,’ ed. by M. A. Fox and M. Chanon, Elsevier, Amsterdam, 1988, Part C, Chap. 4.8, pp. 421-486. 10.1021/ja00791a046 21. N. Kornblum, M. N. Kestner, D. D. Boyd, and L. C. Cattran, J. Am. Chem. Soc., 1973, 95, 3356; R. K. Norris and T. A. Wright, Aust. J. Chem., 1985, 38, 1107; S. M. Palacios, R. A. Alonso, and R. A. Rossi, Tetrahedron, 1985, 41, 4147; H. Miyake and K. Yamamura, Bull. Chem. Soc. Jpn., 1986, 59, 89. 22. The discrepancy of CuCl2 effects on inhibition of the different reactions reflects the importance of the SRN1 reactivity with various anions. Indeed, nitronate anions can react by C-alkylation only through an SRN1 mechanism, so the SRN1 is strongly inhibited in this case. On the other hand, the other anions could follow the both SRN1 and SN2 mechanisms. As a consequence, a partial inhibition is observed. 23. J. Senn-Bilfinger, W. Buhr, and P. Zimmermann, WO 200172748, 2001 (Chem. Abstr., 2001, 135, 272961). 24. C. Amatore, J. Pinson, J.-M. Savéant, and A. Thiébault, J. Am. Chem. Soc., 1982, 104, 817; R. K. Norris and J. A. McMahon, Arkivoc, 2003, X, 139; M. Novi, G. Garbarino, G. Petrillo, and C. Dell’Erba, J. Org. Chem., 1987, 52, 5382; J. A. Zoltewicz and G. A. Locko, J. Org. Chem.,1983, 48, 4214; C. Amatore, C. Combellas, N.-E. Lebbar, A. Thiébault, and J.-N. Verpeaux, J. Org. Chem., 1995, 60, 18.