A new synthesis of pyrazoles through a Lewis acid catalyzed union of 3-ethoxycyclobutanones with monosubstituted hydrazines

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1746-1749

  Shan, Gang ^a   Liu, Pengfei ^a   Rao, Yu ^a  

^a Tsinghua University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; HYDRAZINE DERIVATIVE; LEWIS ACID; PYRAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; CYCLOBUTANES; HYDRAZINES; LEWIS ACIDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRAZOLES;

EID: 79953196169     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2002682     Document Type: Article

References (55)

1. Elguero, J. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 5.
2. Elguero, J.; Goya, P.; Jagerovic, N.; Silva, A. M. S. Targets Heterocycl. Syst. 2002, 6, 52-98
3. Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles, 2 nd ed.; Wiley & Sons: New York, 2004; pp 179 - 184.
4. Sperandeo, N. R.; Brun, R. ChemBioChem 2003, 4, 69
5. Sui, Z.; Guan, J.; Ferro, M. P.; McCoy, K.; Wachter, M. P.; Murray, W. V.; Singer, M.; Steber, M.; Ritchie, D. M.; Argentieri, D. C. Bioorg. Med. Chem. Lett. 2000, 10, 601-604
6. Bekhit, A. A.; Abdel- Aziem, T. Bioorg. Med. Chem. 2004, 12, 1935-1945
7. Selvam, C.; Jachak, S. M.; Thilagavathi, R.; Chakraborti, A. K. Bioorg. Med. Chem. Lett. 2005, 15, 1793-1797
8. Tanitame, A.; Oyamada, Y.; Ofuji, K.; Fujimoto, M.; Suzuki, K.; Ueda, T.; Terauchi, H.; Kawasaki, M.; Nagai, K.; Wachi, M.; Yamagishi, J.-I. Bioorg. Med. Chem. 2004, 12, 5515-5524
9. Stauffer, S. R.; Coletta, C. J.; Tedesco, R.; Nishiguchi, G.; Carlson, K.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2000, 43, 4934-4947
10. Stauffer, S. R.; Huang, Y.; Coletta, C. J.; Tedesco, R.; Katzenellenbogen, J. A. Bioorg. Med. Chem. 2001, 9, 141-150
11. Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347-1365
12. Terrett, N. K.; Bell, A. S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824
13. Singer, R. A.; Caron, S.; McDermott, R. E.; Arpin, P.; Do, N. M. Synthesis 2003, 1727-1732
14. Singer, R. A.; Dore, M.; Sieser, J. E.; Berliner, M. A. Tetrahedron Lett. 2006, 47, 3727-3731
15. Elguero, J. Comp. Heterocycl. Chem. 1984, 5, 167
16. Elguero, J. Compr. Heterocycl. Chem. II 1996, 3, 1-75, 817-932.
17. Makino, K.; Kim, H. S.; Kurasawa, Y. J. Heterocycl. Chem. 1998, 35, 489-497
18. Recent examples about synthesis of pyrazole: Mohanan, K.; Martin, A. R. Angew. Chem., Int. Ed. 2010, 49, 3196-3199
19. Neumann, J. J.; Suri, M. Angew. Chem., Int. Ed. 2010, 49, 7790-7794
20. Lin, Q. Y.; Meloni, D. Org. Lett. 2009, 11, 1999-2002
21. Wang, K.; Xiang, D. Org. Lett. 2008, 10, 1691-1694
22. Mateos, C.; Mendiola, J. Org. Lett. 2010, 12, 4924-4927
23. Okitsu, T.; Sato, K. Org. Lett. 2010, 12, 3506-3509
24. Wu, C. R.; Fang, Y. S. Org. Lett. 2010, 12, 2234-2237
25. Gerstenberger, B. S.; Rauckhorst, M. R. Org. Lett. 2009, 11, 2097-2100
26. Knorr, L. Ber. 1883, 16, 2587
27. Patel, M. V.; Bell, R.; Majest, S.; Henry, R.; Kolasa, T. J. Org. Chem. 2004, 69, 7058-7065
28. Peruncheralathan, S.; Khan, T. A.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70, 10030-10035
29. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565-632
30. Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; John Wiley & Sons: New York, 1984; Vol. I.
31. Padwa, A.; Pearson, W. H., Eds. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; John Wiley & Sons: New York, 2002.
32. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565-632
33. Norris, T.; Colon-Cruz, R.; Ripin, D. H. B. Org. Biomol. Chem. 2005, 3, 1844-1849
34. Bishop, B. C.; Brands, K. M. J.; Gibb, A. D.; Kennedy, D. J. Synthesis 2004, 43-52
35. Miller, R. D.; Reiser, O. J. Heterocycl. Chem. 1993, 30, 755
36. Silva, V. L. M.; Silva, A. M. S.; Pinto, D. C. G. A.; Cavaleiro, J. A. S.; Elguero, J. Eur. J. Org. Chem. 2004, 4348-4356
37. Heller, S. T.; Natarajan, S. R. Org. Lett. 2006, 8, 2675-2678
38. Jung, M. E.; Trifunovich, I. D. Tetrahedron Lett. 1992, 33, 2921-2924
39. Aggarwal, V. K.; Vicente, J.; Bonnert, R. V. J. Org. Chem. 2003, 68, 5381-5383
40. Nakano, Y.; Hamaguchi, M.; Nagai, T. J. Org. Chem. 1989, 54, 5912-5919
41. Foti, F.; Grassi, G.; Risitano, F. Tetrahedron Lett. 1999, 40, 2605-2606
42. Belluš, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1988, 27, 797
43. Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449
44. Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485
45. Aben, R. W.; Scheeren, H. W. J. Chem. Soc., Perkin Trans. 1 1979, 3132-3138
46. Sieja, J. B. J. Am. Chem. Soc. 1971, 93, 130-136
47. Matsuo, J.; Sasaki, S.; Tanaka, H.; Ishibashi, H. J. Am. Chem. Soc. 2008, 130, 11600
48. Matsuo, J.; Okado, R.; Ishibashi, H. Org. Lett. 2010, 12, 3266
49. Matsuo, J.; Sasaki, S.; Hoshikawa, T.; Ishibashi, H. Org. Lett. 2009, 11, 3822
50. Matsuo, J.; Negishi, S.; Ishibashi, H. Tetrahedron Lett. 2009, 50, 5831
51. Intramolecular reaction: Matsuo, J.; Sasaki, S.; Hoshikawa, T.; Ishibashi, H. Chem. Commun 2010, 46, 934
52. For examples about the formation of zwitterionic intermediates from cyclobutane derivatives: Allart, E. A.; Christie, S. D. R.; Pritchard, G. J.; Elsegood, M. R. J. Chem. Commun. 2009, 7339
53. Parsons, A. T.; Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 14202
54. 2 was also tried with different Lewis acid catalysts. Only a trace amount of possible product was observed by LC-MS analysis.
55. Although NMR analysis of crude products did not reveal the presence of the other regioisomers, theoretically the reaction could be regioselective.