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Synthesis of 3-(5H-Pyrazolyl)cyclobutanone Derivatives
Corresponding Author(s) : Pei Yu
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
A 3-(5H-pyrazolyl)-cyclobutanone derivative was synthesized via two different optimized routes. In the first route, the substitutional pyrazole olefins was prepared as a precursor, the target molecule was synthesized via [2 + 2]-cycloaddition by using pyrazols olefins and ketene in total yield of 3 %. In the second route, the four-member ring cyclobutanone fragment was made first, then the pyrazole ring was obtained through cyclization, offering the target molecule with a yield of 8.6 %.
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- A. Chauhan and P.K. Sharma, Int. J. Chem. Technol. Res., 3, 11 (2011).
- D. Bellus and B. Ernst, Angew. Chem. Int. Ed. Engl., 27, 797 (1998); doi:10.1002/anie.198807971.
- J.E. Baldwin, R.M. Adlington, M.F. Parisi and H.-H. Ting, Tetrahedron, 42, 2575 (1986); doi:10.1016/0040-4020(86)80025-4.
- A.J. Cocuzza and G.A. Boswell, Tetrahedron Lett., 26, 5363 (1985); doi:10.1016/S0040-4039(00)98208-X.
- R.W. Friesen, D. Dubé, R. Fortin, R. Frenette, S. Prescott, W. Cromlish, G.M. Greig, S. Kargman, E. Wong, C.C. Chan, R. Gordon, L.J. Xu and D. Riendeau, Bioorg. Med. Chem. Lett., 6, 2677 (1996); doi:10.1016/S0960-894X(96)00501-X.
- W.T. Brady, Synthesis, 415 (1971); doi:10.1055/s-1971-21750.
- S.M. Ali, T.V. Lee and S.M. Roberts, Synthesis, 155 (1977); doi:10.1055/s-1977-24302.
- W.T. Brady, Tetrahedron, 37, 2949 (1981); doi:10.1016/S0040-4020(01)98908-2.
- H.H. Lee, B.F. Cain, W.A. Denny, J.S. Buckleton and G.R. Clark, J. Org. Chem., 54, 428 (1989); doi:10.1021/jo00263a032.
- B.R. Teegarden, H. Li, H. Jayakumar, S. Strah-Pleynet, P.I. Dosa, S.D. Selaya, N. Kato, K.H. Elwell, J. Davidson, K. Cheng, H. Saldana, J.M. Frazer, K. Whelan, J. Foster, S. Espitia, R.R. Webb, N.R.A. Beeley, W. Thomsen, S.R. Morairty, T.S. Kilduff and H.A. Al-Shamma, J. Med. Chem., 53, 1923 (2010); doi:10.1021/jm9007328.
- J. Ramnauth and E. Lee-Ruff, Can. J. Chem., 79, 114 (2001); doi:10.1139/v00-175.
- K.S. Petersen and B.M. Stoltz, Tetrahedron, 67, 4352 (2011); doi:10.1016/j.tet.2011.04.046.
- V.J.B. Falmagne, J. Escudero, S. Taleb-Sahraoui and L. Ghosez, Angew. Chem. Int. Ed. Engl., 93, 926 (1981); doi:10.1002/ange.19810931035.
- J. Smets, Perfume Systems: US Patent 2010137178A1 (2010).
- D. Elend, D. Fengas and M.J. Fray, Synth. Commun., 35, 657 (2005); doi:10.1081/SCC-200050350.
References
A. Chauhan and P.K. Sharma, Int. J. Chem. Technol. Res., 3, 11 (2011).
D. Bellus and B. Ernst, Angew. Chem. Int. Ed. Engl., 27, 797 (1998); doi:10.1002/anie.198807971.
J.E. Baldwin, R.M. Adlington, M.F. Parisi and H.-H. Ting, Tetrahedron, 42, 2575 (1986); doi:10.1016/0040-4020(86)80025-4.
A.J. Cocuzza and G.A. Boswell, Tetrahedron Lett., 26, 5363 (1985); doi:10.1016/S0040-4039(00)98208-X.
R.W. Friesen, D. Dubé, R. Fortin, R. Frenette, S. Prescott, W. Cromlish, G.M. Greig, S. Kargman, E. Wong, C.C. Chan, R. Gordon, L.J. Xu and D. Riendeau, Bioorg. Med. Chem. Lett., 6, 2677 (1996); doi:10.1016/S0960-894X(96)00501-X.
W.T. Brady, Synthesis, 415 (1971); doi:10.1055/s-1971-21750.
S.M. Ali, T.V. Lee and S.M. Roberts, Synthesis, 155 (1977); doi:10.1055/s-1977-24302.
W.T. Brady, Tetrahedron, 37, 2949 (1981); doi:10.1016/S0040-4020(01)98908-2.
H.H. Lee, B.F. Cain, W.A. Denny, J.S. Buckleton and G.R. Clark, J. Org. Chem., 54, 428 (1989); doi:10.1021/jo00263a032.
B.R. Teegarden, H. Li, H. Jayakumar, S. Strah-Pleynet, P.I. Dosa, S.D. Selaya, N. Kato, K.H. Elwell, J. Davidson, K. Cheng, H. Saldana, J.M. Frazer, K. Whelan, J. Foster, S. Espitia, R.R. Webb, N.R.A. Beeley, W. Thomsen, S.R. Morairty, T.S. Kilduff and H.A. Al-Shamma, J. Med. Chem., 53, 1923 (2010); doi:10.1021/jm9007328.
J. Ramnauth and E. Lee-Ruff, Can. J. Chem., 79, 114 (2001); doi:10.1139/v00-175.
K.S. Petersen and B.M. Stoltz, Tetrahedron, 67, 4352 (2011); doi:10.1016/j.tet.2011.04.046.
V.J.B. Falmagne, J. Escudero, S. Taleb-Sahraoui and L. Ghosez, Angew. Chem. Int. Ed. Engl., 93, 926 (1981); doi:10.1002/ange.19810931035.
J. Smets, Perfume Systems: US Patent 2010137178A1 (2010).
D. Elend, D. Fengas and M.J. Fray, Synth. Commun., 35, 657 (2005); doi:10.1081/SCC-200050350.