Convenient synthesis of polysubstituted 3-iodofurans through the tandem ring-opening/cyclization reaction of 1-alkynyl-2,3-epoxy alcohols

Synthesis

Volumn , Issue 21, 2007, Pages 3295-3300

  Wen, Shu Guang ^a,b   Liu, Wei Min ^a   Liang, Yong Min ^a,c  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c LANZHOU UNIVERSITY   (China)

Author keywords

Electrophilic cyclization; Epoxide; Iodofuran; Tandem reaction

Indexed keywords

ELECTROPHILIC CYCLIZATION; IODOFURAN; TANDEM REACTIONS;

CYCLIZATION; EPOXIDATION; REACTION RATES; RING OPENING POLYMERIZATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

FURAN RESINS;

1 (ARYLETHYNYL) 2,3 EPOXY ALCOHOL DERIVATIVE; ALCOHOL DERIVATIVE; FURAN DERIVATIVE; IODINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; RING OPENING; SUBSTITUTION REACTION; SYNTHESIS;

EID: 36448939800     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990830     Document Type: Article

References (37)

1. (a) Katritzky, A. R. Advances in Heterocyclic Chemistry; Academic Press: New York, 1982.
2. (b) Sargent, M. V.; Dean, F. M. In Comprehensive Heterocyclic Chemistry, Vol. 4; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: New York, 1984, 599-656.
3. (c) Nakanishi, K. Natural Products Chemistry; Kodansha: Tokyo, 1974.
4. (d) Bird, C. W.; Cheeseman, G. W. H. In Comprehensive Heterocyclic Chemistry, Vol. 4; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: New York, 1984.
5. For pharmaceuticals, see, for example: Mortensen, D. S.; Rodrigues, A. L.; Karlson, K. E.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2001, 44, 3838.
6. Recent reviews: (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry, Vol. 14; Gribble, G. W.; Gilchrist, T. L., Eds.; Pergamon Press: Oxford, 2002, 139-179.
7. (b) Cacchi, S. J. Organomet. Chem. 1999, 576, 42-64.
8. (c) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
9. Brown, R. C. D. Angew. Chem. Int. Ed. 2005, 44, 850.
10. (a) Sheng, H.; Lin, S.; Huang, Y. Tetrahedron Lett. 1986, 27, 4893.
11. (b) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816.
12. (c) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95.
13. (d) Ma, S.; Zhang, J. Chem. Commun. 2000, 117.
14. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem. Int. Ed. 2000, 39, 2285.
15. (f) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 960.
16. (g) Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 59, 7169.
17. (a) Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655.
18. (b) Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687.
19. (c) Seiller, B.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1994, 493.
20. (d) Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089.
21. (a) Lo, C.-Y.; Guo, H.; Lian, J.-J.; Shen, F.-M.; Liu, R.-S. J. Org. Chem. 2002, 67, 3930.
22. (b) Marshall, J. A.; DuBay, W. J. J. Am. Chem. Soc. 1992, 114, 1450.
23. (c) Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432.
24. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
25. Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
26. (a) El-Taeb, G. M. M.; Evans, A. B.; Jones, S.; Knight, D. W. Tetrahedron Lett. 2001, 42, 5945.
27. (b) Bew, S. P.; Knight, D. W. Chem. Commun. 1996, 1007.
28. Schultz-Fademrecht, C.; Zimmermann, M.; Fröhlich, R.; Hoppe, D. Synlett 2003, 1969.
29. (a) Chinchilla, R.; Najera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
30. (b) Tanabe, Y.; Wakimura, K.; Nishii, Y.; Muroya, Y. Synthesis 1996, 388.
31. For C-C bond formation, see: (c) Lin, S.-Y.; Chen, C.-L.; Lee, Y.-J. J. Org. Chem. 2003, 68, 2968.
32. (d) Bach, T.; Krüger, L. Eur. J. Org. Chem. 1999, 2045.
33. For C-N bond formation, see: (e) Hooper, M. W.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861.
34. (f) Padwa, A.; Crawford, K. R.; Rashatasakhon, P.; Rose, M. J. Org. Chem. 2003, 68, 2609.
35. For C-S bond formation, see: (g) Arroyo, Y.; Rodriguez, J. F.; Sanz-Tejedor, M. A.; Santos, M. Tetrahedron Lett. 2002, 43, 9129.
36. Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles, 2nd ed.; Wiley-VCH: Weinheim, 2003, 52-62.
37. Boger, D. L. Modern Organic Synthesis; TSRI Press: La Jolla, 1999, 45-48.