Syntheses of substituted furans and pyrroles by platinum-catalyzed cyclizations of propargylic oxiranes and aziridines in aqueous media

Synthesis

Volumn , Issue 14, 2009, Pages 2454-2466

  Yoshida, Masahiro ^a   Al Amin, Mohammad ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Alkyne; Epoxide; Furan; Platinum; Pyrrole

Indexed keywords

ALKYNE; AQUEOUS MEDIA; AZIRIDINES; CATALYZED REACTIONS; CYCLIZATIONS; EPOXIDE; FUNCTIONALIZED; FURAN; GOOD YIELD; HIGH EFFICIENCY; N-IODOSUCCINIMIDE; OXIRANES; PLATINUM CATALYSTS; PYRROLE;

ACETYLENE; CATALYSIS; CATALYSTS; NITROGEN COMPOUNDS; POTASSIUM COMPOUNDS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

PLATINUM;

AZIRIDINE DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; FURAN DERIVATIVE; IODINE DERIVATIVE; PLATINUM; PYRROLE DERIVATIVE; SUCCINIMIDE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; BIOTRANSFORMATION; CATALYSIS; CYCLIZATION; HECK REACTION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 67651112166     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216867     Document Type: Article

References (48)

1. (a) Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, 395.
2. (b) Piozzi, F.; Bruno, M.; Rosselli, S.; Maggio, A. Heterocycles 2007, 74, 31.
3. (c) Fan, H.; Peng, J.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264.
4. (d) Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213.
5. (a) Patterson, J. M. Synthesis 1976, 281.
6. (b) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
7. (c) Tsubuki, M. J. Synth. Org. Chem., Jpn. 1993, 51, 399.
8. (d) Piancatelly, G.; D'Auria, M.; D'Onofrio, F. Synthesis 1994, 867.
9. (e) Wong, H. N. C. Pure Appl. Chem. 1996, 68, 335.
10. (f) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179.
11. (g) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105.
12. (h) Schroeter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245.
13. (a) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193.
14. (b) 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.
15. (c) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076.
16. (d) Balme, G.; Bouyssi, D.; Monteiro, N. Heterocycles 2007, 73, 87.
17. (e) Patil, N. T.; Yamamoto, Y. ARKIVOC 2007, (x), 121.
18. (f) Schmuck, C.; Rupprecht, D. Synthesis 2007, 3095.
19. (g) Balme, G.; Bouyssi, D.; Monteiro, N. Heterocycles 2007, 73, 84.
20. (h) Ono, N. Heterocycles 2008, 75, 243.
21. (a) Berbalk, H.; Eichinger, K.; Winetzhammer, W. Helv. Chim. Acta 1981, 64, 1026.
22. (b) Ribereau, P.; Queguiner, G. Can. J. Chem. 1983, 61, 334.
23. (c) Marshall, J. A.; DuBay, W. J. J. Org. Chem. 1991, 56, 1685.
24. (d) Katritzky, A. R.; Li, J. J. Org. Chem. 1995, 60, 638.
25. (e) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363.
26. (f) Aurrecoechea, J. M.; Pérez, E.; Solay, M. J. Org. Chem. 2001, 66, 564.
27. (g) Lo, C.-Y.; Guo, H.; Lian, J.-J.; Shen, F.-M.; Liu, R.-S. J. Org. Chem. 2002, 67, 3930.
28. (h) Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432.
29. (i) Blanc, A.; Tenbrink, K.; Weibel, J.-M.; Pale, P. J. Org. Chem. 2009, 74, 4360.
30. (a) Yoshida, M.; Ueda, H.; Ihara, M. Tetrahedron Lett. 2005, 46, 6705.
31. (b) Yoshida, M.; Morishita, Y.; Ihara, M. Tetrahedron Lett. 2005, 46, 3669.
32. (c) Yoshida, M.; Hayashi, M.; Shishido, K. Org. Lett. 2007, 9, 1643.
33. (d) Yoshida, M.; Hayashi, M.; Matsuda, K.; Shishido, K. Heterocycles 2009, 77, 193.
34. (a) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271.
35. (b) Fürstner, A.; Davies, P. D. Angew. Chem. Int. Ed. 2007, 46, 3410.
36. One part of the results on our preliminary studies has been published: Yoshida, M.; Al-Amin, M.; Matsuda, K.; Shishido, K. Tetrahedron Lett. 2008, 49, 5021.
37. Hashmi also reported the conversion of 1i using a gold catalyst, in which the reaction was complete in 17 h affording 2i in 80% yield; see ref 4h.
38. Enhancement of the reactivity for a gold-catalyzed reaction in water has been reported: Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953.
39. Similar transformations using gold catalysts have been reported: (a) Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515.
40. (b) Buzas, A.; Istrate, F.; Gagosz, F. Org. Lett. 2006, 8, 1957.
41. (c) Crone, B.; Kirsh, S. F. J. Org. Chem. 2007, 72, 5435.
42. Recently, Liu reported the synthesis of 3-iodofurans by electrophilic cyclization of propargylic oxiranes using iodine: Xie, Y.-X.; Liu, X. Y.; Wu, L.-Y.; Han, Y.; Zhao, L.-B.; Fan, M.-J.; Liang, Y. M. Eur. J. Org. Chem. 2008, 1013.
43. Joullié reported the byproduction of a pyrrole when a ring-opening reaction of a propargylic aziridine using CuOAc and DBU was attempted: Forbeck, E. M.; Evans, C. D.; Gilleran, J. A.; Li, P.; Joullié, M. M. J. Am. Chem. Soc. 2007, 129, 14463.
44. During the preparation of this manuscript, the gold-catalyzed cyclization of propargylic aziridines was reported: Davies, P. W.; Martin, N. Org. Lett. 2009, 11, 2293.
45. Chemla, F.; Ferreira, F.; Hebbe, V.; Stercklen, E. Eur. J. Org. Chem. 2002, 1385.
46. Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716.
47. Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677.
48. Shavrin, K. N.; Gvozdev, V. D.; Nefedov, O. M. Mendeleev Commun. 1995, 5, 181.