4
Tetrahedron
7. Li, F.; Nie, J.; Sun, L.; Zheng, Y.; Ma, J. –A. Angew. Chem. Int. Ed.
2013, 52, 6255.
prepared hydrazonoyl halides or their analogue and β-
oxophosphonates with wide scope and functional group
compatibility. This new reaction pathway was carried out
smoothly at room temperature in good yields with excellent
regioselectivity which should provide better access to pyrazole
molecules for the pharmaceutical industry and general synthetic
interest. The plausible reaction mechanism was also proposed.
8. Catarzi, D.; Colotta, V.; Varano, F.; Guido, F., Calli, A.; Costagli, C.;
Carla, V. J. Med. Chem. 2001, 44, 3157.
9. (a) Shawali, A. S.; Hassaneen, H. M.; Tetrahedron 1973, 29, 121; (b)
Tanaka, K.; Kishida, M.; Maeno, S.; Mitsuhashi, K. Bull. Chem. Soc.
Jpn. 1986, 59, 2631; (c) Hassaneen, H. M.; Abdelhamid, A. O.; Fahmi,
A.; Shawali, A. S. J. Heterocycl. Chem. 1985, 22, 395; (d) Shawali, A.
S. J. Heterocycl. Chem. 1977, 14, 375; (e) Bravo, P.; Diliddo, D.;
Resnati, G. Tetrahedron Lett. 1994, 29, 8827.
R1
N
R1
R1
OH
R3
O
NH
NH
- Cl
route 2
10. Yan, B.; Spilling, C. D. J. Org. Chem. 2008, 73, 5385.
11. (a) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.;
Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25,
2183; (b) Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624;
(c) Lattanzi, A.; Orelli, L. R.; Barone, P.; Massa, A.; Iannece, P.;
Scettri, A. Tetrahedron Lett. 2003, 44, 1333.
1
N
N
N
R3
R2
Cl
O
PO(OEt)2
11
R2
R2
PO(OEt)2
H
B
9
H
R3
route 1
B
(EtO)2OP
B
4
- H2O
B
- H+
12. Hill, S. E.; Feller, D.; Glendening, E. D. J. Phys. Chem. A 1998, 102,
3813.
13. Jiang, J. –A.; Huang, W. -B.; Zhai, J. –J.; Liu, H. –W.; Cai, Q.; Xu, L.
–X.; Wang, W.; Ji, Y. –F. Tetrahedron 2013, 69, 627.
R1
R1
R1
R3
R3
N
N
N
R3
O-
N
N
N
O
R2
O-
P
R2
PO(OEt)2
H
R2
H
PO(OEt)2
EtO
OEt
12
- PO(OEt)2O-
10
6
R1
N
R3
N
5
R2
H
Scheme 4. Plausible reaction mechanism
Acknowledgments
This project was funded by the Priority Academic Program
Development of Jiangsu Higher Education Institutions (PAPD),
and we thank Nanjing University of Chinese Medicine for
financial support
Supplementary data
Supplementary material associated with this article can be
found, in the online version, at doi:
References and notes
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