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Synthesis of Some Novel Pyrazolopyridooxazine, Pyrazoloquinolizines, Pyrazoloindolizine and Pyrazolopyranopyrimidinone Derivatives
Corresponding Author(s) : Hissah H. Al-Tilasi
Asian Journal of Chemistry,
Vol. 26 No. 13 (2014): Vol 26 Issue 13
Abstract
Different pyrazolone derivatives were prepared as starting materials for the synthesis of pyrazolopyridooxazine, pyrazoloquinolizines, pyrazoloindolizine, 1,4-oxazinopyrazolines and pyrazolopyranopyrimidinone derivatives via reactions with different reagents applying the one pot multicomponent reaction using microwave and ultrasound irradiation in some cases.
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- I. Çelik, N. KanIskan and S. Kökten, Tetrahedron, 65, 328 (2009); doi:10.1016/j.tet.2008.10.047.
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- H.A. DeWald, S. Lobbestael and B.P.H. Poschel, J. Med. Chem., 24, 982 (1981); doi:10.1021/jm00140a013.
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- H.A. Abdel-Aziz, A.A.I. Mekawey and K.M. Dawood, Eur. J. Med. Chem., 44, 3637 (2009); doi:10.1016/j.ejmech.2009.02.020.
- A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, N. Fathalla and F.M.E. Abdel-Megeid, Eur. J. Med. Chem., 44, 3285 (2009); doi:10.1016/j.ejmech.2009.02.012.
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- H.A. Abdel-Aziz, H.S.A. El-Zahabi and K.M. Dawood, Eur. J. Med. Chem., 45, 2427 (2010); doi:10.1016/j.ejmech.2010.02.026.
- B.P. Bandgar, J.V. Totre, S.S. Gawande, C.N. Khobragade, S.C. Warangkar and P.D. Kadam, Bioorg. Med. Chem., 18, 6149 (2010); doi:10.1016/j.bmc.2010.06.046.
- F. El-Baih and H.M. Al-Hazimi, Asian J. Chem., 23, 1309 (2011).
- A.M. Farag, K.A.K. Ali, T.M.A. El-Debss, A.S. Mayhoub, A.-G.E. Amr, N.A. Abdel-Hafez and M.M. Abdulla, Eur. J. Med. Chem., 45, 5887 (2010); doi:10.1016/j.ejmech.2010.09.054.
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- J. Becher, P.L. Joergensen, K. Pluta, N.J. Krake and B. Falt-Hansen, J. Org. Chem., 57, 2127 (1992); doi:10.1021/jo00033a039.
- D. Prajapati and K.J. Borah, Beilstein J. Org. Chem., 3, 43 (2007); doi:10.1186/1860-5397-3-43
- T.M. Al-Mutairi, H.M. Al-Hazimi and F.E.M. El-Baih, J. Saudi Chem. Soc., 13, 199 (2009); doi:10.1016/j.jscs.2009.06.001.
- Y.A. Sharanin, V.K. Promonenkov and L.G. Sharanina, J. Org. Chem. (USSR), 18, 544 (1982).
- D.L. Pavia, G.M. Lampman, G.S. Kriz and J.R. Vyvyan, Introduction to Spectroscopy, Thmoson Learning, edn. 4 (2009).
References
I. Çelik, N. KanIskan and S. Kökten, Tetrahedron, 65, 328 (2009); doi:10.1016/j.tet.2008.10.047.
T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997); doi:10.1021/jm960803q.
M. Rinaldi-Carmona, F. Barth, M. Héaulme, D. Shire, B. Calandra, C. Congy, S. Martinez, J. Maruani, G. Néliat, D. Caput, P. Ferrara, P. Soubrié, J.C. Brelière and G. Le Fur, FEBS Lett., 350, 240 (1994); doi:10.1016/0014-5793(94)00773-X.
H.A. DeWald, S. Lobbestael and B.P.H. Poschel, J. Med. Chem., 24, 982 (1981); doi:10.1021/jm00140a013.
K.S. Girisha, B. Kalluraya, V. Narayana and Padmashree, Eur. J. Med. Chem., 45, 4640 (2010); doi:10.1016/j.ejmech.2010.07.032.
A.M. Isloor, B. Kalluraya and K. Sridhar Pai, Eur. J. Med. Chem., 45, 825 (2010); doi:10.1016/j.ejmech.2009.11.015.
A.M. Youssef, M. Sydney White, E.B. Villanueva, I.M. El-Ashmawy and A. Klegeris, Bioorg. Med. Chem., 18, 2019 (2010); doi:10.1016/j.bmc.2010.01.021.
P.-C. Lv, J. Sun, Y. Luo, Y. Yang and H.-L. Zhu, Bioorg. Med. Chem. Lett., 20, 4657 (2010); doi:10.1016/j.bmcl.2010.05.105.
S. Bondock, R. Rabie, H.A. Etman and A.A. Fadda, Eur. J. Med. Chem., 43, 2122 (2008); doi:10.1016/j.ejmech.2007.12.009.
X.-H. Liu, J. Zhu, A. Zhou, B.-A. Song, H.-L. Zhu, L.-S. Bai, P.S. Bhadury and C.-X. Pan, Bioorg. Med. Chem., 17, 1207 (2009); doi:10.1016/j.bmc.2008.12.034.
N.P. Rai, V.K. Narayanaswamy, S. Shashikanth and P.N. Arunachalam, Eur. J. Med. Chem., 44, 4522 (2009); doi:10.1016/j.ejmech.2009.06.020.
H.A. Abdel-Aziz, A.A.I. Mekawey and K.M. Dawood, Eur. J. Med. Chem., 44, 3637 (2009); doi:10.1016/j.ejmech.2009.02.020.
A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, N. Fathalla and F.M.E. Abdel-Megeid, Eur. J. Med. Chem., 44, 3285 (2009); doi:10.1016/j.ejmech.2009.02.012.
A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, J.A. Micky and F.M.E. Abdel-Megeid, Bioorg. Med. Chem., 16, 7102 (2008); doi:10.1016/j.bmc.2008.06.054.
M.M. Ghorab, F.A. Ragab, S.I. Alqasoumi, A.M. Alafeefy and S.A. Aboulmagd, Eur. J. Med. Chem., 45, 171 (2010); doi:10.1016/j.ejmech.2009.09.039.
H.A. Abdel-Aziz, H.S.A. El-Zahabi and K.M. Dawood, Eur. J. Med. Chem., 45, 2427 (2010); doi:10.1016/j.ejmech.2010.02.026.
B.P. Bandgar, J.V. Totre, S.S. Gawande, C.N. Khobragade, S.C. Warangkar and P.D. Kadam, Bioorg. Med. Chem., 18, 6149 (2010); doi:10.1016/j.bmc.2010.06.046.
F. El-Baih and H.M. Al-Hazimi, Asian J. Chem., 23, 1309 (2011).
A.M. Farag, K.A.K. Ali, T.M.A. El-Debss, A.S. Mayhoub, A.-G.E. Amr, N.A. Abdel-Hafez and M.M. Abdulla, Eur. J. Med. Chem., 45, 5887 (2010); doi:10.1016/j.ejmech.2010.09.054.
S.K. Meegalla, D. Doller, G.M. Silver, N. Wisnewski, R.M. Soll and D. Dhanoa, Bioorg. Med. Chem. Lett., 13, 4035 (2003); doi:10.1016/j.bmcl.2003.08.042.
G.P. Lahm, T.M. Stevenson, T.P. Selby, J.H. Freudenberger, D. Cordova, L. Flexner, C.A. Bellin, C.M. Dubas, B.K. Smith, K.A. Hughes, J.G. Hollingshaus, C.E. Clark and E.A. Benner, Bioorg. Med. Chem. Lett., 17, 6274 (2007); doi:10.1016/j.bmcl.2007.09.012.
S. Gupta, A. Sivasubramanian, L.M. Rodrigues, A.P. Esteves, R. Hrdina and A.M.F. Oliveira-Campos, Dyes Pigments, 75, 82 (2007); doi:10.1016/j.dyepig.2006.04.016.
A.A. Al-Mutairi, F.E.M. El-Baih and H.M. Al-Hazimi, J. Saudi Chem. Soc., 14, 287 (2010); doi:10.1016/j.jscs.2010.02.010.
J. Becher, P.L. Joergensen, K. Pluta, N.J. Krake and B. Falt-Hansen, J. Org. Chem., 57, 2127 (1992); doi:10.1021/jo00033a039.
D. Prajapati and K.J. Borah, Beilstein J. Org. Chem., 3, 43 (2007); doi:10.1186/1860-5397-3-43
T.M. Al-Mutairi, H.M. Al-Hazimi and F.E.M. El-Baih, J. Saudi Chem. Soc., 13, 199 (2009); doi:10.1016/j.jscs.2009.06.001.
Y.A. Sharanin, V.K. Promonenkov and L.G. Sharanina, J. Org. Chem. (USSR), 18, 544 (1982).
D.L. Pavia, G.M. Lampman, G.S. Kriz and J.R. Vyvyan, Introduction to Spectroscopy, Thmoson Learning, edn. 4 (2009).