Divergent construction of pyrazoles via Michael addition of n -arylhydrazones to 1,2-diaza-1,3-dienes

Organic Letters

Volumn 17, Issue 8, 2015, Pages 2014-2017

  Mantenuto, Serena ^a   Mantellini, Fabio ^a   Favi, Gianfranco ^a   Attanasi, Orazio A ^a  

^a UNIVERSITY OF URBINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; HETEROCYCLIC COMPOUND; HYDRAZONE DERIVATIVE; PYRAZOLE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKADIENES; AZA COMPOUNDS; HYDRAZONES; MOLECULAR STRUCTURE; PYRAZOLES;

EID: 84928036450     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00776     Document Type: Article

References (49)

1. Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239
2. Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231
3. Miyata, O.; Miyoshi, T.; Ueda, M. ARKIVOC 2013, 60
4. Grobel, B. T.; Seebach, D. Synthesis 1977, 357
5. For reviews, see: Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 11686
6. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
7. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534
8. Chen, M. Z.; Gutierrez, O.; Smith, A. B. Angew. Chem., Int. Ed. 2014, 53, 1279
9. Lee, K.; Kim, H.; Hong, J. Angew. Chem., Int. Ed. 2012, 51, 5735
10. Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: Weinheim, 1996.
11. Nicolaou, K. C.; Snyder, S. A. Classics in Total Synthesis II; Wiley-VCH: Weinheim, 2003.
12. Tatum, L. A.; Su, X.; Aprahamian, I. Acc. Chem. Res. 2014, 47, 2141
13. Su, X.; Aprahamian, I. Chem. Soc. Rev. 2014, 43, 1963
14. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
15. Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. Chem. Rev. 2011, 111, 6984
16. Mantovani, A. C.; Goulart, T. A. C.; Back, D. F.; Zeni, G. Chem.-Eur. J. 2014, 20, 1
17. Safaei, S.; Mohammadpoor-Baltork, I.; Khosropour, A. R.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V. New J. Chem. 2013, 37, 2037
18. Aljaar, N.; Conrad, J.; Beifuss, U. J. Org. Chem. 2013, 78, 1045
19. Duan, X. Y.; Yang, X. L.; Fang, R.; Peng, X. X.; Yu, W.; Han, B. J. Org. Chem. 2013, 78, 10692
20. Xu, X.; Zavalij, P. Y.; Doyle, M. P. Angew. Chem., Int. Ed. 2012, 51, 9829
21. Lemos, A. In Targets in Heterocyclic Systems-Chemistry and Properties; Attanasi, O. A.; Spinelli, D., Eds.; Società Chimica Italiana: Rome, 2010; Vol. 14, p 1.
22. Attanasi, O. A.; De Crescentini, L.; Favi, G.; Filippone, P.; Mantellini, F.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2009, 3109
23. Guo, C.; Sahoo, B.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17402
24. Gao, S.; Chen, J.-R.; Hu, X.-Q.; Cheng, H.-G.; Lu, L.-Q.; Xiao, W.-J. Adv. Synth. Catal. 2013, 355, 3539
25. Attanasi, O. A.; Favi, G.; Geronikaki, A.; Mantellini, F.; Moscatelli, G.; Paparisva, A. Org. Lett. 2013, 15, 2624
26. Attanasi, O. A.; Bianchi, L.; Campisi, L. A.; De Crescentini, L.; Favi, G.; Mantellini, F. Org. Lett. 2013, 15, 3646
27. Chen, J.-R.; Dong, W.-R.; Candy, M.; Pan, F.-F.; Jorres, M.; Bolm, C. J. Am. Chem. Soc. 2012, 134, 6924
28. Hatcher, J. M.; Coltart, D. M. J. Am. Chem. Soc. 2010, 132, 4546
29. Serrano, I.; Monge, D.; álvarez, E.; Fernández, R.; Lassaletta, J. M. Chem. Commun. 2015, 51, 4077
30. Yang, H.-B.; Zhao, Y.-Z.; Sang, R.; Shi, M. J. Org. Chem. 2014, 79, 3519
31. Wu, W.; Yuan, X.; Hu, J.; Wu, X.; Wei, Y.; Liu, Z.; Lu, J. Org. Lett. 2013, 15, 4524
32. Monge, D.; Daza, S.; Bernal, P.; Fernández, R.; Lassaletta, J. M. Org. Biomol. Chem. 2013, 11, 326
33. Fernández, M.; Uria, U.; Vicario, J. L.; Reyes, E.; Carrillo, L. J. Am. Chem. Soc. 2012, 134, 11872
34. Peña, A. C.; Monge, D.; Martín-Zamora, E.; álvarez, E.; Fernández, R.; Lassaletta, J. M. J. Am. Chem. Soc. 2012, 134, 12912
35. Deng, X.; Mani, N. S. Org. Lett. 2008, 10, 1307
36. El Kaim, L.; Gautier, L.; Grimaud, L.; Michaut, V. Synlett 2003, 1844
37. Baldwin, J. E.; Adlington, R. M.; Bottaro, J. C.; Kolhe, J. N.; Perry, M. W. D.; Jain, A. U. Tetrahedron 1986, 42, 4223
38. Deng, X.; Mani, N. S. J. Org. Chem. 2008, 73, 2412
39. Deng, X.; Mani, N. S. Org. Lett. 2006, 8, 3505
40. An alternative pathway in which CH/NH tautomerization may precede the cyclization step should be excluded according to our previous findings. See: Attanasi, O. A.; Filippone, P.; Fiorucci, C.; Mantellini, F. Tetrahedron Lett. 1999, 40, 3891
41. Elguero, J.; Goya, P.; Jagerovic, N.; Silva, A. M. S. In Targets in Heterocyclic Systems-Chemistry and Properties; Attanasi, O. A.; Spinelli, D., Eds.; Società Chimica Italiana: Rome, 2002; Vol. 6, p 52.
42. Kost, A. N.; Grandberg, I. I. In Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J., Eds.; Academic Press: New York, 1996; Vol. 6, p 347.
43. Tewari, A. K.; Singh, V. P.; Yadav, P.; Gupta, G.; Singh, A.; Goel, R. K.; Shinde, P.; Mohan, C. G. Bioorg. Chem. 2014, 56, 8
44. Riyadh, S. M. Molecules 2011, 16, 1834
45. Thapa, D.; Lee, J. S.; Heo, S. W.; Lee, Y. R.; Kang, K. W.; Kwak, M. K.; Choi, H. G.; Kim, J. A.; Thapa, D. Eur. J. Pharmacol. 2011, 650, 64
46. Ismail, M. A. H.; Lehmann, J.; Abou El Ella, D. A.; Albohy, A.; Abouzid, K. A. M. Med. Chem. Res. 2009, 18, 725
47. Zhang, H.-h.; Dou, W.; Liu, W.-s.; Tang, X.-l.; Qin, W.-w. Eur. J. Inorg. Chem. 2011, 748
48. Guo, J.; Jia, L.; Liu, L.; Yuan, H.; Li, F. J. Mater. Chem. 2011, 21, 3210
49. Guo, J.; Liu, L.; Liu, G.; Jia, D.; Xie, X. Org. Lett. 2007, 9, 3989