Phl(OAc)2-mediated novel 1,3-dipolar cycloaddition of Methylenecyclopropanes (MCPs), Vinylidenecyclopropanes (VCPs), and Methylenecyclobutane (MCB) with phthalhydrazide

Organic Letters

Volumn 9, Issue 7, 2007, Pages 1303-1306

  Liu, Le Ping ^a   Lu, Jian Mei ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34147125865     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070178r     Document Type: Article

References (56)

1. For synthesis of MCPs: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
2. For recent reviews on MCPs, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
3. (b) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89.
4. (c) Binger, P.; Wedemann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 113.
5. (d) de Meijere, A.; Kozhushkov, S. I. Eur. J. Org. Chem. 2000, 3809.
6. (e) Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111.
7. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
8. (g) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
9. See ref 2f and references cited therein, also see: (a) Molchanov, A. P.; Diev, V. V.; Magull, J.; Vidovic, D.; Kozhushkov, S. I.; de Meijere, A.; Kostikov, R. R. Eur. J. Org. Chem. 2005, 593.
10. (b) de Meijere, A.; Becker, H.; Stolle, A.; Kozhushkov, S. I.; Bes, M. T.; Salaün, J,; Noltemeyer, M. Chem. Eur. J. 2005, 11, 2471.
11. (c) Krafft, M. E.; Boñaga, L. V. R.; Felts, A. S.; Hirosawa, C.; Kerrigan, S. J. Org. Chem. 2003, 68, 6039.
12. (d) Shi, M.; Shao, L.-X.; Xu, B. Org. Lett. 2003, 5, 579.
13. Selected recent articles on MCPs: (a) Siriwardana, A. I.; Kamada, M.; Nakamura, I.; Yamamoto, Y. J. Org. Chem. 2005, 70, 5932.
14. (b) Nakamura, I.; Nemoto, T.; Yamamoto, Y.; de Meijere, A. Angew. Chem., Int. Ed. 2006, 45, 5176.
15. (c) Saito, S.; Masuda, M.; Komagawa, S. J. Am. Chem. Soc. 2004, 126, 10540.
16. (d) Gulías, M.; García, R.; Delgado, A.; Castedo, L.; Mascareñas, J. L. J. Am. Chem. Soc. 2006, 128, 384.
17. (e) Delgado, A.; Rodríguez, J. R.; Castedo, L.; Mascareñas, J. L. J. Am. Chem. Soc. 2003, 125, 9282.
18. (f) Rajamaki, S.; Kilburn, J. D. Chem. Commun. 2005, 1637.
19. (g) Patient, L.; Berry, M. B.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1015.
20. (h) Scott, M. E.; Schwarz, C. A.; Lautens, M. Org. Lett. 2006, 8, 5521.
21. (i) Scott, M. E.; Lautens, M. Org. Lett. 2005, 7, 3045.
22. (j) Kamikawa, K.; Shimizu, Y.; Takemoto, S.; Matsuzaka, H. Org. Lett. 2006, 8, 4011.
23. (k) Murakami, M.; Ishida, N.; Miura, T. Chem. Commun. 2006, 643.
24. (l) Yu, L.; Huang, X.; Xie, M. Synlett 2006, 423.
25. (m) Chen, W.; Huang, X.; Zhou, H.; Ren, L. Synthesis 2006, 609.
26. (n) Huang, X.; Fu, W. J. Synthesis 2006, 1016.
27. (o) Li, Q.; Shi, M.; Timmons, C.; Li, G. Org. Lett. 2006, 8, 625.
28. (p) Shao, L. X.; Xu, B.; Huang, J. W.; Shi, M. Chem. Eur. J. 2006, 12, 510.
29. (q) Shi, M.; Wang, B.-Y.; Huang, J.-W. J. Org. Chem. 2005, 70, 5606.
30. (r) Shi, M.; Liu, L.-P.; Tang, J. J. Am. Chem. Soc. 2006, 128, 7430.
31. (s) Shi, M.; Liu, L.-P.; Tang, J. Org. Lett. 2006, 8, 4043.
32. Selected recent examples, see: (a) Zanobini, A.; Brandi, A.; de Meijere, A. Eur. J. Org. Chem. 2006, 1251.
33. (b) Revuelta, J.; Cicchi, S.; Brandi, A. J. Org. Chem. 2005, 70, 5636.
34. (c) Cordero, F. M.; Salvati, M.; Pisaneschi, F.; Brandi, A. Eur. J. Org. Chem. 2004, 2205.
35. (d) Marradi, M.; Brandi, A.; de Meijere, A. Synlett 2006, 1125.
36. (e) Marradi, M.; Brandi, A.; Magull, J.; Schill, H.; de Meijere, A. Eur. J. Org. Chem. 2006, 5485 and references cited therein.
37. Li, J.; Liang, J. L.; Chan, P. W. H.; Che, C. M. Tetrahedron Lett. 2004, 45, 2685 and references cited therein.
38. (a) Krasnova, L. B.; Yudin, A. K. Org. Lett. 2006, 8, 2011.
39. (b) Watson, I. D. G.; Yu, L.; Yudin, A. K. Acc. Chem. Res. 2006, 39, 194 and references cited therein.
40. Liang, Y.; Jiao, L.; Wang, Y.; Chen, Y.; Ma, L.; Xu, J.; Zhang, S.; Yu, Z.-X. Org. Lett. 2006, 8, 5877.
41. w 0.0470, 0.1026.
42. Selected recent articles on VCPs, see: (a) Mizuno, K.; Sugita, H.; Hirai, T.; Maeda, H. Chem. Lett. 2000, 1144.
43. (b) Mizuno, K.; Maeda, H.; Sugita, H.; Nishioka, S.; Hirai, T.; Sugimoto, A. Org. Lett. 2001, 3, 581.
44. (c) Mizuno, K.; Sugita, H.; Kamada, T.; Otsuji, Y. Chem. Lett. 1994, 449.
45. (d) Maeda, H.; Hirai, T.; Sugimoto, A.; Mizuno, K. J. Org. Chem. 2003, 68, 7700.
46. (e) Shi, M.; Lu, J.-M. J. Org. Chem. 2006, 71, 1920.
47. (f) Shi, M.; Lu, J.-M. Synlett 2005, 2352.
48. (g) Shi, M.; Ma, M.; Shao, L.-X. Tetrahedron Lett. 2005, 46, 7609.
49. (h) Shi, M.; Lu, J.-M.; Xu, G.-C. Tetrahedron Lett. 2005, 46, 4745.
50. (i) Xu, G.-C.; Ma, M.; Liu, L.-P.; Shi, M. Synlett 2005, 1869.
51. (j) Xu, G.-C.; Liu, L.-P.; Lu, J.-M.; Shi, M. J. Am. Chem. Soc. 2005, 127, 14552.
52. (k) Shao, L.-X.; Zhang, Y.-P.; Qi, M.-H.; Shi, M. Org. Lett. 2007, 9, 117.
53. 4 or N-bromosuccinimide (NBS), see: (a) Contreras, F. G.; Loratamayo, M.; Sanz, A. M. Heterocycles 1987, 25, 193.
54. (b) Contreras, F. G.; Lora-tamayo, M.; Sanz, A. M. Heterocycles 1989, 28, 791.
55. (c) Coxon, J. M.; O' Connel, M. J.; Steel, P. J. J. Org. Chem. 1987, 52, 4726.
56. Phthalazine-1,4-dione was often employed in aza-Diels-Alder reactions as the dienophile, see ref 11. To our best knowledge, however, there are no articles that reported it could react as a 1,3-dipole.