One-pot synthesis of 3-substituted isoquinolin-1-(2H)-ones and fused isoquinolin-1-(2H)-ones by SRN1 reactions in DMSO

European Journal of Organic Chemistry

Volumn , Issue 17, 2006, Pages 3898-3902

  Guastavino, Javier F ^a   Barolo, Silvia M ^a   Rossi, Roberto A ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

Electron transfer SRN1 reaction; Fused ring systems; Nucleophilic substitution; Radicals

Indexed keywords

EID: 33748548368     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600244     Document Type: Article

References (31)

1. M. S. Chern, W. R. Li, Tetrahedron Lett. 2004, 45, 8323-8326.
2. V. A. Glushkov, Y. V. Shklyaev, Chem. Heterocycl. Compd. 2001, 37, 663-687.
3. D. Gonzalez, T. Martinot, T. Hudlickly, Tetrahedron Lett. 1999, 40, 3077-3080.
4. R. C. Thompson, J. Kallmerten, J. Org. Chem. 1990, 55, 6076-6078.
5. S. Senda, O. Ohtani, E. Katho, H. Miyake, K. Fujiwara, Ger. Offen. 3031574, 1981 [Chem. Abstr. 1981, 95, 132692].
6. K. Kubo, N. Ito, I. Souzu, Y. Isomura, H. Homma, Ger. Offen. 2828528, 1979 [Chem. Abstr. 1979, 90, 168468].
7. S. Senda, O. Ohtani, E. Katho, M. Nagasaka, H. Miyake, K. Fujiwara, M. Tanaka, Fr. Demande 2502619, 1983 [Chem. Abstr. 1983, 98, 71955].
8. M. Hasegava, K. Shirai, K. Matsumoto, Y. Suzuki, I. Takahasi, US Patent 5441962, 1994 [Chem. Abstr. 1994, 121, 912].
9. S. Senda, O. Ohtani, E. Katho, M. Nagasaka, H. Miyake, K. Fujiwara, M. Tanaka, Ger. Offen. 3211501, 1982 [Chem. Abstr. 1983, 95, 198048].
10. F. Coelho, D. Veronese, E. C. S. Lopes, R. C. Rossi, Tetrahedron Lett. 2003, 44, 5731-5735.
11. P. G. Jagtap, E. Baloglu, G. Southan, W. Williams, A. Roy, A. Nivorozhkin, N. Landrau, K. Desisto, A. L. Salzman, C. Szabó, Org. Lett. 2005, 7, 1753-1756.
12. S. Otha, S. Kimoto, Tetrahedron Lett. 1975, 16, 2279-2282.
13. L. E. Fisher, J. M. Muchowski, R. D. Clark, J. Org. Chem. 1992, 57, 2700-2705.
14. R. J. Snow, T. Butz, A. Hammach, S. Kapadia, T. M. Morwick, A. S. Prokopowicz, H. Takahashi, J. D. Tan, M. A. Tschantza, X. Wangb, Tetrahedron Lett. 2002, 43, 7553-7556.
15. K. Cherry, A. Duchêne, J. Thibonnet, J. L. Parrain, M. Abarbri, Synthesis 2005, 2349-2355.
16. For reviews, see: a) R. A. Rossi, A. B. Pierini, A. B. Peñéñory in The Chemistry of Functional Groups (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1995, Supplement D2, ch. 24, pp. 1395-1485;
17. RN1 Reaction" in Organic Reactions (Eds.: L. A. Paquette, R. Bittman), John Wiley & Sons, New York, 1999, vol. 54, pp. 1-271;
18. c) R. A. Rossi, A. B. Pierini, A. B. Peñéñory, Chem. Rev. 2003, 103, 71-167.
19. RN1 Mechanism" in Targets in Heterocyclic Systems: Chemistry and Properties (Eds.: O. A. Attanasi, D. Spinelli), Societa Chimica Italiana, Rome, 1999, vol. 3, pp. 215-243.
20. W. J. Layman, T. D. Greenwood, A. L. Downey, J. F. Wolfe, J. Org. Chem. 2005, 70, 9147-9155.
21. M. D. Roydhouse, J. C. Walton, Chem. Commun. 2005, 4453-4455.
22. S. M. Barolo, A. E. Lukach, R. A. Rossi, J. Org. Chem. 2003, 68, 2807-2811, and references therein.
23. R. Beugelmans, M. Bois-Choussy, Synthesis 1981, 729-731.
24. R. Beugelmans, M. Bois-Choussy, Tetrahedron 1992, 48, 8285-8294.
25. R. Beugelmans, M. Bois-Choussy, J. Org. Chem. 1991, 56, 2518-2522.
26. R. A. Moss, S. Chatterjee, W. Boguslawa, J. Org. Chem. 1986, 51, 4303-4307.
27. E. Bisagni, C. Landras, S. Thirot, C. Huel, Tetrahedron 1996, 52, 10427-10439.
28. W. J. Cho, M. J. Park, B. H. Chung, C. O. Lee, Bioorg. Med. Chem. Lett. 1998, 8, 41-46.
29. Although this compound was synthesized, no product characterization was reported, see: W. J. Cho, S. Y. Min, T. N. Le, T. S. Kim, Bioorg. Med. Chem. Lett. 2003, 13, 4451-4454.
30. E. M. Brun, S. Gil, M. Parra, Arkivoc 2002, X, 80-89.
31. J. H. Rigby, D. D. Holsworth, K. James, J. Org. Chem. 1989, 54, 4019-4020.