Bicyclization of diazomethanes: A synthetic strategy for fused pyrazoles

Advanced Synthesis and Catalysis

Volumn 355, Issue 8, 2013, Pages 1540-1544

  Wang, He ^a   Zhao, Yu Long ^a   Li, Lei ^a   Zhang, Zhen Wei ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

bicyclization; diazomethanes; fused pyrazoles; tandem reaction; withasomnines

Indexed keywords

EID: 84878248200     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201201062     Document Type: Article

References (30)

1. H.-B. Schröter, D. Neumann, A. R. Katritzky, F. J. Swinbourne, Tetrahedron 1966, 22, 2895.
2. S. A. Adesanya, R. Nia, C. Fontaine, M. Païs, Phytochemistry 1994, 35, 1053
3. A. J. Aladesanmi, R. Nia, A. Nahrstedt, Planta Med. 1998, 64, 90
4. P. J. Houghton, R. Pandey, J. E. Hawkes, Phytochemistry 1994, 35, 1602.
5. V. Ravikanth, P. Ramesh, P. V. Diwan, Y. Venkateswarlu, Biochem. Syst. Ecol. 2001, 29, 753.
6. A. A. Wube, E.-M. Wenzig, S. Gibbons, K. Asres, R. Bauer, F. Bucar, Phytochemistry 2008, 69, 982.
7. B. Singh, A. K. Saxena, B. K. Chandan, D. K. Gupta, K. K. Bhutani, K. K. Anand, Phytother. Res. 2001, 15, 311
8. L. Davis, G. Kuttan, J. Exp. Clin. Cancer Res. 2002, 21, 115.
9. R. Kumar, I. N. N. Namboothiri, Org. Lett. 2011, 13, 4016 (three steps starting from α-diazo-β-ketosulfone with nitroalkenes)
10. S. Majumder, K. R. Gipson, R. J. Staples, A. L. Odom, Adv. Synth. Catal. 2009, 351, 2013 (six steps, 24% overall yield)
11. O. Kulinkovich, N. Masalov, V. Tyvorskii, N. De Kimpe, M. Keppens, Tetrahedron Lett. 1996, 37, 1095 (eight steps)
12. H. Ichikawa, R. Watanabe, Y. Fujino, Y. Usami, Tetrahedron Lett. 2011, 52, 4448 (over ten steps starting from pyrazole)
13. R. S. Foster, J. Huang, J. F. Vivat, D. L. Browne, J. P. A. Harrity, Org. Biomol. Chem. 2009, 7, 4052 (four steps from proline-derived sydnone).
14. H.-y. Li, W. T. McMillen, C. R. Heap, D. J. Mccann, L. Yan, R. M. Campbell, S. R. Mundla, C.-H. R. King, E. A. Dierks, B. D. Anderson, K. S. Britt, K. L. Huss, M. D. Voss, Y. Wang, D. K. Clawson, J. M. Yingling, J. S. Sawyer, J. Med. Chem. 2008, 51, 2302
15. H.-y. Li, Y. Wang, C. R. Heap, C.-H. R. King, S. R. Mundla, M. Voss, D. K. Clawson, L. Yan, R. M. Campbell, B. D. Anderson, J. R. Wagner, K. Britt, K. X. Lu, W. T. McMillen, J. M. Yingling, J. Med. Chem. 2006, 49, 2138
16. D. L. Browne, J. F. Vivat, A. Plant, E. Gomez-Bengoa, J. P. A. Harrity, J. Am. Chem. Soc. 2009, 131, 7762.
17. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, (Eds.:, A. Padwa, W. H. Pearson,), Wiley, Hoboken, 2003
18. S. Fustero, M. Sánchez-Roselló, P. Barrio, A. Simón-Fuentes, Chem. Rev. 2011, 111, 6984
19. Y. L. Janin, Chem. Rev. 2012, 112, 3924.
20. D. J. Babinski, H. R. Aguilar, R. Still, D. E. Frantz, J. Org. Chem. 2011, 76, 5915
21. D. Simovic, M. Di, V. Marks, D. C. Chatfield, K. S. Rein, J. Org. Chem. 2007, 72, 650, and references cited therein.
22. R. Kumar, D. Verma, S. M. Mobin, I. N. N. Namboothiri, Org. Lett. 2012, 14, 4070
23. R. S. Foster, H. Jakobi, J. P. A. Harrity, Org. Lett. 2012, 14, 4858
24. X. Qi, J. M. Ready, Angew. Chem. 2007, 119, 3306
25. Angew. Chem. Int. Ed. 2007, 46, 3242.
26. A. Gioiello, A. Khamidullina, M. C. Fulco, F. Venturoni, S. Zlotsky, R. Pellicciari, Tetrahedron Lett. 2009, 50, 5978 (synthesis of pyrazole-5- carboxylates by 1,3-dipole cycloadditions of ethyl diazoacetate with α-methylene carbonyl compounds).
27. 2-catalyzed C-C coupling reaction of α-iodo-α-cinnamoyl ketene dithioacetals with terminal alkenes, see
28. H. Wang, Y.-L. Zhao, C.-Q. Ren, A. Diallo, Q. Liu, Chem. Commun. 2011, 47, 12316.
29. L. Zhang, X. Xu, W. Xia, Q. Liu, Adv. Synth. Catal. 2011, 353, 2619.
30. D. Verma, S. Mobin, I. N. N. Namboothiri, J. Org. Chem. 2011, 76, 4764.