Studies on the synthesis of 3-substituted benzo[b]furanes by intramolecular SNAr on 2-(2′-fluoroaryl)-2-(1-azolylmethyl)oxiranes

Arkivoc

Volumn 2007, Issue 4, 2007, Pages 234-250

  Santamaria, Antoni ^a   Moreno Mañas, Marcial ^a   Pleixats, Roser ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Azole derivatives; Benzo b furans; Heterocycles; Intramolecular aromatic nucleophilic substitution; Oxiranes

Indexed keywords

EID: 33846038642     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.420     Document Type: Article

References (33)

1. Friedriichsen, W. Furanes and their Benzo Derivatives: Synthesis. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 2, Chapter 7.
2. (a) Beak, P.; Reitz, D. B. Chem. Rev. 1978, 78, 275.
3. (b) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471.
4. (c) Cuberes, M. R.; Moreno-Mañas, M.; Trius, A. Synthesis 1985, 302.
5. (d) Shimizu, S.; Ogata, M. J. Org. Chem. 1986, 51, 3897.
6. (e) Shimizu, S.; Ogata, M. J. Org. Chem. 1987, 52, 2314.
7. (f) Shimizu, S.; Ogata, M. Tetrahedron 1989, 45, 637.
8. (g) Moreno-Mañas, M.; Bassa, J.; N. Lladó; Pleixats, R. J. Heterocycl. Chem. 1990, 27, 673.
9. (a) Boyle, F. T. Eur. Pat. Appl 122,693, 1984.
10. (b) Y. Arredondo, Ph. D. thesis, Universitat Autònoma de Barcelona, 1996.
11. Godefroi, E.; Heeres, J.; Van Cutsem, J. J. Med. Chem. 1969, 12, 784.
12. (a) Hurd, R. E.; John, B. K. J. Magn. Reson. 1991, 91, 648.
13. (b) Parella, T.; Sánchez-Ferrando, F.; Virgili, A. J. Magn. Reson. 1995, 112, 241.
14. (a) Astleford, B. A.; Goe, G. L.; Keay, J. G.; Scriven, E. F. V. J. Org. Chem. 1989, 54, 731.
15. (b) Katjár-Peredy, M.; Bauer, L. J. Heterocycl. Chem. 1997, 34, 637.
16. (a) Akgün, E.; Glinski, M.; Dhawan, K.; Durst, T. J. Org. Chem. 1981, 46, 2730.
17. (b) Gololobov, Y., Nesmeyanov, A.; Lysenko, V.; Boldeskul, I. Tetrahedron 1987, 42, 2609.
18. Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749.
19. (a) Schwesinger, R.; Hasenfratz, C.; Schlemper, H.; Walz, L.; Peters, E. M.; Peters, K.; Von Schnering, H. Angew. Chem. Int. Ed. 1993, 32, 1361.
20. (b) Tang, J.; Dopke, J.; Verkade, J. G. J. Am. Chem. Soc. 1993, 115, 5015.
21. Narayanan, A.; Chapman, D. R.; Upadhyaya, S. P.; Bauer, L. J. Heterocycl. Chem. 1993, 30, 1405.
22. (a) Teixidó, M.; Ph.D. Thesis, Universitat Autònoma de Barcelona 1992.
23. (b) Sledzinski, B; Cieslak, L.; Zawadzki, M. Pol. Organika 1979, 1.
24. Chem. Abstr. 94, 83719.
25. Chapman, D. R.; Bauer, L. J. Heterocycl. Chem. 1990, 27, 2053
26. (a) Itoh, K.; Okonogi, K. Eur. Pat. Appl. EP0421210, 1991; Chem. Abstr.115, 92271.
27. (b) Richardson, K.; Gymer, G. E. Eur. Pat. Appl. EP0153803, 1985; Chem. Abstr. 104, 109650.
28. (c) Richardson, K.; Gymer, G. E. Eur. Pat. Appl. EP0118245, 1984; Chem. Abstr. 102, 45953.
29. Kalendra, D. M.; Sickles, B. R. J. Org. Chem. 2003, 68, 1594.
30. Moreno-Mañas, M.; Arredondo, Y.; Pleixats, R.; Teixidó, M.; Raga, M. M.; Palacín, C.; Castelló, J. M.; Ortiz, J. A. J. Heterocyclic Chem. 1992, 29, 1557.
31. Richardson, K., Brit. UK Pat. Appl. 2,099,818, 1982; Chem. Abstr. 99, 38467.
32. Babin, D.; Weston, J. PCT Int. Appl. WO02090350, 2002; Chem. Abstr. 137, 353032.
33. Richardson, K.; Narayanaswami, S. Eur. Pat. Appl. EP0122056, 1984; Chem. Abstr. 102, 132042.