Phosphazene base-catalyzed intramolecular cyclization for efficient synthesis of benzofurans via carbon-carbon bond formation

Chemical Communications

Volumn , Issue 35, 2009, Pages 5248-5250

  Kanazawa, Chikashi ^a   Goto, Kengo ^a   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; CARBON;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 69549091878     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b913588j     Document Type: Article

References (31)

1. Methoden Der Organischen Chemie (Houben-Weyl), ed., R. P. Kreher, Georg Thieme Verlag, Stuttgart, 1994, vol. E6b, p. 33
2. Science of Synthesis, ed., E. J. Thomas, Georg Thieme Verlag, Stuttgart, 2000, vol. 10, p. 11
3. C. Martínez R. Álvarez J. M. Aurrecoechea Org. Lett. 2009 11 1083
4. Z. Liang S. Ma J. Yu R. Xu Tetrahedron 2007 63 12877
5. B. M. Trost A. McClory Angew. Chem., Int. Ed. 2007 46 2074
6. R. Bernini S. Cacchi I. D. Salve G. Fabrizi Synthesis 2007 873
7. M. Nakamura L. Ilies S. Otsubo E. Nakamura Angew. Chem., Int. Ed. 2006 45 944
8. Y. Hu K. J. Nawoschik Y. Liao J. Ma R. Fathi Z. Yang J. Org. Chem. 2004 69 2235
9. Y. Hu Y. Zhang Z. Yang R. Fathi J. Org. Chem. 2002 67 2365
10. G. Zeni R. C. Larock Chem. Rev. 2006 106 4644
11. F. Manarin J. A. Roehrs R. M. Gay R. Brandão P. H. Menezes C. W. Nogueira G. Zeni J. Org. Chem. 2009 74 2153
12. I. Nakamura Y. Mizushima U. Yamagishi Y. Yamamoto Tetrahedron 2007 63 8670
13. A. Fürstner P. W. Davies J. Am. Chem. Soc. 2005 127 15024
14. I. Nakamura Y. Mizushima Y. Yamamoto J. Am. Chem. Soc. 2005 127 15022
15. S. Cacchi G. Fabrizi L. Moro Tetrahedron Lett. 1998 39 5101 5104
16. N. Monteiro G. Balme Synlett 1998 746
17. S. Cacchi G. Fabrizi L. Moro Synlett 1998 741
18. J. Li T. S. Rush, III W. Li D. DeVincentis X. Du Y. Hu J. R. Thomason J. S. Xiang J. S. Skotnicki S. Tam K. M. Cunningham P. S. Chockalingam E. A. Morris J. I. Levin Bioorg. Med. Chem. Lett. 2005 15 4961
19. K. K. Park J. Jeong Tetrahedron 2005 61 545
20. G. A. Kraus N. Zhang J. Verkade M. Nagarajan P. Kisanga Org. Lett. 2000 2 2409
21. D. Shikanai H. Murase T. Hata H. Urabe J. Am. Chem. Soc. 2009 131 3166
22. R. Schwesinger H. Schlemper Angew. Chem., Int. Ed. Engl. 1987 26 1167
23. R. Schwesinger C. Hasenfratz Angew. Chem., Int. Ed. Engl. 1993 32 1361
24. R. Schwesinger H. Schlemper C. Hasenfratz J. Willaredt T. Dambacher T. Breuer C. Ottaway M. Fletschinger J. Boele H. Fritz D. Putzas H. W. Rotter F. G. Bordwell A. V. Satish G.-Z. Ji E.-M. Peters K. Peters H. G. Schnering L. Walz Liebigs Ann. Chem. 1996 1055
25. tBu efficiently accelerated the 5-exo specific intramolecular cyclization reaction of o-alkynylbenzamides, providing isoindolinone derivatives having the exo-vinylidene moiety, in which the presence/absence of a protic additive, water in this case, was found to be crucial in controlling the geometry at the exo-double bond, see: C. Kanazawa, M. Terada, to be submitted
26. Y. Murcus J. Solution Chem. 1984 13 599
27. C. Reichardt E. Harbusch-Görnert Liebigs Ann. Chem. 1983 721
28. C. Laurence P. Nicolet C. Reichardt Bull. Soc. Chim. Fr. 1987 125
29. T. Imahori C. Hori Y. Kondo Adv. Synth. Catal. 2004 346 1090
30. C. Kanazawa M. Terada Tetrahedron Lett. 2007 48 933
31. M. Terada C. Kanazawa M. Yamanaka Heterocycles 2007 74 819