Diazirines as potent electrophilic Nitrogen sources: Application to the synthesis of Pyrazoles

Organic Letters

Volumn 16, Issue 2, 2014, Pages 596-599

  Schneider, Yoann ^a   Prévost, Julie ^a   Gobin, Maëlle ^a   Legault, Claude Y ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84896762429     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403495e     Document Type: Article

References (49)

1. Sundberg, R. J. Indoles; Academic Press: San Diego, 1999; p 54.
2. Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 607.
3. Katritzky, A. R. Handbook of Heterocyclic Chemistry; Pergamon: New York, 1985; p 416.
4. Ragnarsson, U. Chem. Soc. Rev. 2001, 30, 205.
5. Fischer, E. Justus Liebigs Ann. Chem. 1878, 190, 67.
6. Fischer, E. Ber. Dtsch. Chem. Ges. 1875, 8, 1005.
7. Hunsberger, I. M.; Shaw, E. R.; Fugger, J.; Ketcham, R.; Lednicer, D. J. Org. Chem. 1956, 21, 394.
8. Monoprotected hydrazines: (a) Reichelt, A.; Falsey, J. R.; Rzasa, R. M.; Thiel, O. R.; Achmatowicz, M. M.; Larsen, R. D. Org. Lett. 2010, 12, 792.
9. Barluenga, J.; Moriel, P.; Aznar, F.; Valdés, C. Org. Lett. 2007, 9, 275.
10. Lim, Y.-K.; Jung, J.-W.; Lee, H.; Cho, C.-G. J. Org. Chem. 2004, 69, 5778.
11. Lim, Y.-K.; Lee, K.-S.; Cho, C.-G. Org. Lett. 2003, 5, 979.
12. Wang, Z.; Skerlj, R. T.; Bridger, G. J. Tetrahedron Lett. 1999, 40, 3543. Hydrazones
13. Lefebvre, V.; Cailly, T.; Fabis, F.; Rault, S. J. Org. Chem. 2010, 75, 2730.
14. Mauger, C.; Mignani, G. Adv. Synth. Catal. 2005, 347, 773.
15. Lebedev, A. Y.; Khartulyari, A. S.; Voskoboynikov, A. Z. J. Org. Chem. 2005, 70, 596.
16. Cho, C. S.; Lim, D. K.; Heo, N. H.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2004, 104.
17. Arter-burn, J. B.; Rao, K. V.; Ramdas, R.; Dible, B. R. Org. Lett. 2001, 3, 1351.
18. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
19. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
20. Monoprotected hydrazines: (a) Rivero, M. R.; Buchwald, S. L. Org. Lett. 2007, 9, 973.
21. Martín, R.; Rodríguez Rivero, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 7079.
22. Loog, O.; Mäeorg, U. Synlett 2004, 2537.
23. Tsubrik, O.; Maeorg, U.; Sillard, R.; Ragnarsson, U. Tetrahedron 2004, 60, 8363.
24. Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
25. King, F. D.; Walton, D. R. M. Synthesis 1975, 738. Hydrazones
26. Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
27. Pabba, C.; Wang, H.-J.; Mulligan, S. R.; Chen, Z.-J.; Stark, T. M.; Gregg, B. T. Tetrahedron Lett. 2005, 46, 7553.
28. Inamoto, K.; Katsuno, M.; Yoshino, T.; Suzuki, I.; Hiroya, K.; Sakamoto, T. Chem. Lett. 2004, 33, 1026.
29. Lundgren, R. J.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 8686.
30. Gerstenberger, B. S.; Rauckhorst, M. R.; Starr, J. T. Org. Lett. 2009, 11, 2097.
31. Velarde-Ortiz, R.; Guijarro, A.; Rieke, R. D. Tetrahedron Lett. 1998, 39, 9157.
32. Demers, J. P.; Klaubert, D. H. Tetrahedron Lett. 1987, 28, 4933.
33. Inman, M.; Carbone, A.; Moody, C. J. J. Org. Chem. 2012, 77, 1217.
34. Armstrong, A.; Jones, L. H.; Knight, J. D.; Kelsey, R. D. Org. Lett. 2005, 7, 713.
35. Ciganek, E. Org. React. 2008, 72, 1.
36. Schmitz, E. Dreiringe mit zwei Heteroatomen, Oxaziridine, Diaziridine, Cyclische Diaziverbindungen; Springler-Verlag: Berlin, 1967.
37. Liu, M. T. H. Chemistry of Diazirines; CRC Press, Inc.: 1987.
38. Ohme, R.; Schmitz, E.; Dolge, P. Chem. Ber. 1966, 99, 2104.
39. Paget, C. J.; Davis, C. S. J. Med. Chem. 1964, 7, 626.
40. Schmitz, E.; Schinkowski, K. Chem. Ber. 1964, 97, 1964.
41. Schmitz, E.; Ohme, R. Chem. Ber. 1962, 95, 795.
42. Schmitz, E.; Ohme, R. Chem. Ber. 1961, 94, 2166.
43. The synthesis of N-alkyl hydrazines from 3,3-pentamethylene diazirine was reported but is not reproducible and results in degradation products: Schmitz, E.; Ohme, R. Angew. Chem. 1961, 73, 220.
44. Das, J. Chem. Rev. 2011, 111, 4405.
45. Goldman, D. W.; Pober, J. S.; White, J.; Bayley, H. Nature 1979, 280, 841.
46. Ye, Q.; Komarov, I. V.; Kirby, A. J.; Jones, M., Jr. J. Org. Chem. 2002, 67, 9288.
47. Makhova, N. N.; Shevtsov, A. V.; Petukhova, V. Y. Russ. Chem. Rev. 2011, 80, 1035.
48. McDonald, E.; Jones, K.; Brough, P. A.; Drysdale, M. J.; Workman, P. Curr. Top. Med. Chem. 2006, 6, 1193.
49. Elguero, J. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; Vol. 5.