Copper(II)/copper(I)-catalyzed aza-michael addition/click reaction of in situ generated α-azidohydrazones: Synthesis of novel pyrazolone-triazole framework

Organic Letters

Volumn 12, Issue 3, 2010, Pages 468-471

  Attanasi, Orazio A ^a   Favi, Glanfranco ^a   Filippone, Paolino ^a   Mantellini, Fabio ^a   Moscatelli, Giada ^a   Perrulli, Francesca R ^a  

^a UNIVERSITY OF URBINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; COPPER; HYDRAZONE DERIVATIVE; PYRAZOLONE; PYRAZOLONE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; COPPER; CYCLIZATION; HYDRAZONES; MOLECULAR STRUCTURE; PYRAZOLONES; TRIAZOLES;

EID: 75749112494     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902642z     Document Type: Article

References (44)

1. See, for example: The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 2000; Vol.54;and others in this series.
2. (a) Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337-2347.
3. (b) Duggers, R. W.; Ragan, J. A.; Brown Ripin, D. H. Org. Process Res. Dev. 2005, 9, 253-258.
4. For a review on copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis, see: Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054-3131.
5. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
6. Huisgen, R. 1, 3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol.1, pp 1-177.
7. (a) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3062.
8. (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
9. For general reviews on the chemistry of 1, 2, 3-triazoles, see: (a) Fan, W.-Q.; Katritzky, A. R. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1986; Vol.4, pp 1-126.
10. For some applications in organic synthesis, see: (b) Dichtel, W. R.; Miljanic, O. S.; Spruel, J. M.; Health, J. R.; Stoddart, J. F. J. Am. Chem. Soc. 2006, 128, 10388-10390. In combinatorial chemistry, see:
11. (c) Rodriguez-Loaiza, P.; Löber, S.; Hübner, H.; Gmeiner, P. J. Comb. Chem. 2006, 8, 252-261. In bioconjugation, see:
12. (d) Cavalli, S.; Tipton, A. R.; Ovarhand, M.; Kros, A. Chem. Commun. 2006, 3193-3195. In materials and surface science, see:
13. (e) Such, G. K.; Quinn, J. F.; Quinn, A.; Tjipto, E.; Caruso, F. J. Am. Chem. Soc. 2006, 128, 9318-9319.
14. For recent reviews on the preparation of a wide variety of triazolecontaining molecules by CuAAC, see: (a) Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015.
15. (b) Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68.
16. (c) Kolb, H. C.; Sharpless, K. B. Drug. Disc. Today 2003, 8, 1128-1137.
17. Ito, S.; Satoh, A.; Nagatomi, Y.; Hirata, Y.; Suzuki, G.; Kimura, T.; Satow, A.; Maehara, S.; Hikichi, H.; Hata, M.; Kawamoto, H.; Ohta, H. Bioorg. Med. Chem. 2008, 16, 9817-9829.
18. Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.; Wang, Q. Org. Lett. 2004, 6, 4603-4606.
19. Attanasi, O. A.; Serra-Zanetti, F.; Liao, Z. Tetrahedron 1992, 48, 2785-2792.
20. For review on the chemistry of DDs, see: (a) Attanasi, O. A.; De Crescentini, L.; Favi, G.; Filippone, P.; Mantellini, F.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2009, 3109-3127. For recent examples, see:
21. (b) Attanasi, O. A.; Berretta, S.; De Crescentini, L.; Favi, G.; Giorgi, G.; Mantellini, F. Adv. Synth. Catal. 2009, 351, 715-719.
22. (c) Attanasi, O. A.; Favi, G.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Org. Lett. 2008, 11, 309-312.
23. For use of L-ascorbic acid in organic synthesis, see: Füger, B. Synlett 2009, 848-849.
24. For copper(II) acetate monohydrate as catalyst in the Michael reaction, see: Coda, A. C.; Desimoni, G.; Rigetti, P.; Tacconi, G. Gazz. Chim. Ital. 1984, 114, 417-420.
25. 3 as versatile reagent in organic synthesis,
26. see: Jafarzadeh, M. Synlett 2009, 2144-2145.
27. For examples of TMSN3 as azide source in Michael addition, see: (a) Castrica, L.; Fringuelli, F.; Gregoli, L.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2006, 71, 9536-9539, and references cited herein,
28. (b) Adamo, I.; Benedetti, F.; Berti, F.; Campaner, P. Org. Lett. 2006, 8, 51-54.
29. (c) Guerin, D. J.; Horstmann, T. E.; Miller, S. J. Org. Lett. 1999, 1, 1107-1109.
30. Attention: The main concern about this one-pot procedure may appear a serious safety issue. In fact it is well documented in the literature that ionic azides react with dichloromethane to form explosive azidochloromethane and/or diazidomethane. See: (a) Conrow, R. E.; Dean, W. D. Org. Process Res. Dev. 2008, 12, 1285-1286.
31. 2 is effectively suppressed since the Michael addition is the favorite and exclusive pathway.
32. 3 and we encountered no problem.
33. Attanasi, O. A.; Favi, G.; Filippone, P.; Lillini, S.; Mantellini, F.; Spinelli, D.; Stenta, M. Adv. Synth. Catal. 2007, 349, 907-915.
34. For representative examples of one-pot synthesis of 1, 2, 3-triazoles, see: (a) Li, J.; Wang, D.; Zhang, Y.; Li, J.; Chen, B. Org. Lett. 2009, 11, 3024-3027.
35. (b) Jaroslaw, K.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171-3174.
36. (c) Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081-3084.
37. (d) Beckmann, H. S. G.; Wittmann, V. Org. Lett. 2007, 9, 1-4.
38. (e) Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223-4225.
39. DDs 1a-g were synthesized from the corresponding chlorohydrazones by treatment with base (see Supporting Information).
40. For reviews on single-pot catalysis of different transformations, see: (a) Shindoh, N.; Takemoto, Y.; Takasu, K. Chem.-Eur. J. 2009, 15, 12168-12179.
41. (b) Ajamian, A.; Gleason, J. L. Angew. Chem., Int. Ed. Engl. 2004, 43, 3754-3760. For some interesting examples of sustainable synthetic methods, see:
42. (c) Alaimo, P. G.; O'Brien, R., III.; Johnson, A. W.; Slauson, S. R.; O'Brien, J. M.; Tyson, E. L.; Marshall, A.-L.; Ottinger, C. E.; Chacon, J. G.; Wallace, L.; Paulino, C. Y.; Connell, S. Org. Lett. 2008, 10, 5111-5114.
43. (d) Heutling, A.; Pohlki, F.; Byschkov, I.; Doye, S. Angew. Chem., Int. Ed. 2005, 44, 2951-2954.
44. (e) Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958-2963.