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Condensation of 7-Nitroindole-2-carbohydrazide Derivatives with Ethyl Acetoacetate
Corresponding Author(s) : Abdellatif El-Kihel
Asian Journal of Chemistry,
Vol. 28 No. 6 (2016): Vol 28 Issue 6
Abstract
Pyrazolylindolyl ketone derivatives were obtained by cyclization of the condensation products 7-nitroindole-2-carbohydrazide derivatives with ethyl acetoacetate. We have shown careful examination of spectroscopic data and the open-chain intermediate isolation as well as the identification of the formed compound structure.
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- J.T. Kuethe, A. Wong, C. Qu, J. Smitrovich, I.W. Davies and D.L. Hughes, J. Org. Chem., 70, 2555 (2005); doi:10.1021/jo0480545.
- A.L. Smith, G.L. Stevenson, C.J. Swain and J.L. Castro, Tetrahedron Lett., 39, 8317 (1998); doi:10.1016/S0040-4039(98)01824-3.
- M. Jyothi and M. Merugu, Int. J. Pharm. Tech. Res., 8, 80 (2015).
- T. Penning, J. Talley, S. Bertenshaw, J. Carter, P. Collins, S. Docter, M. Graneto, L. Lee, J. Malecha, J. Miyashiro, R. Rogers, D. Rogier, S. Yu, G. Anderson, E. Burton, N. Cogburn, S. Gregory, C. Koboldt, S. Perkins, K. Seibert, A. Veenhuizen, Y. Zhang and P. Isakson, J. Med. Chem., 40, 1347 (1997); doi:10.1021/jm960803q.
- J. Dumas, H. Hatoum-Mokdad, R. Sibley, B. Riedl, W.J. Scott, M.K. Monahan, T.B. Lowinger, C. Brennan, R. Natero, T. Turner, J.S. Johnson, R. Schoenleber, A. Bhargava, S.M. Wilhelm, T.J. Housley, G.E. Ranges and A. Shrikhande, Bioorg. Med. Chem. Lett., 10, 2051 (2000); doi:10.1016/S0960-894X(00)00272-9.
- A. El Kihel, M. Ahbala, T. Harjane, E.M. Essassi and P. Bauchat, Phys. Chem. News, 34, 85 (2007).
- A. El Kihel, A. Lagnaoui, T. Harjane, Y. Kattir, S. Guesmi and P. Bauchat, Arabian J. Chem., 6, 173 (2013); doi:10.1016/j.arabjc.2010.09.032.
- M. El Ouar, N. Knouzi, A. El Kihel, E.M. Essassi, M. Benchidmi, J. Hamelin, R. Carrié and R. Danion-Bougot, Synth. Commun., 25, 1601 (1995); doi:10.1080/00397919508015844.
- A. Errossafi, A. El Kihel, S. Guesmi, M. Saadi and L. El Ammari, Acta Crystallogr., E71, o684 (2015); doi:10.1107/S2056989015015054.
- Abdel-Rahman and A.H. Farghaly, J. Chin. Chem. Soc., 51, 147 (2004); doi:10.1002/jccs.200400023.
- S. Hiremath, A. Ullagaddi, K. Sekhar and M.G. Purohit, Indian J. Chem., 27B, 758 (1988).
- Farhanullah, A. Sharon, P.R. Maulik and V. Ji Ram, Tetrahedron Lett., 45, 5099 (2004); doi:10.1016/j.tetlet.2004.04.172.
- M. Jukic, M. Cetina, G. Pavlovic and V. Rapic, Struct. Chem., 10, 85 (1999); doi:10.1023/A:1022077012526.
- N.M. Przheval’skii, N.S. Skvortsova and I.V. Magedov, Chem. Heterocycl. Compd., 40, 1435 (2004); doi:10.1007/s10593-005-0061-3.
- A. El Kihel, M. Ahbala, A. Mouzdahir, N. Snader, E. Mokhtar Essassi, P. Bauchat and R. Danion-Bougot, Synth. Commun., 38, 200 (2008); doi:10.1080/00397910701738933.
References
J.T. Kuethe, A. Wong, C. Qu, J. Smitrovich, I.W. Davies and D.L. Hughes, J. Org. Chem., 70, 2555 (2005); doi:10.1021/jo0480545.
A.L. Smith, G.L. Stevenson, C.J. Swain and J.L. Castro, Tetrahedron Lett., 39, 8317 (1998); doi:10.1016/S0040-4039(98)01824-3.
M. Jyothi and M. Merugu, Int. J. Pharm. Tech. Res., 8, 80 (2015).
T. Penning, J. Talley, S. Bertenshaw, J. Carter, P. Collins, S. Docter, M. Graneto, L. Lee, J. Malecha, J. Miyashiro, R. Rogers, D. Rogier, S. Yu, G. Anderson, E. Burton, N. Cogburn, S. Gregory, C. Koboldt, S. Perkins, K. Seibert, A. Veenhuizen, Y. Zhang and P. Isakson, J. Med. Chem., 40, 1347 (1997); doi:10.1021/jm960803q.
J. Dumas, H. Hatoum-Mokdad, R. Sibley, B. Riedl, W.J. Scott, M.K. Monahan, T.B. Lowinger, C. Brennan, R. Natero, T. Turner, J.S. Johnson, R. Schoenleber, A. Bhargava, S.M. Wilhelm, T.J. Housley, G.E. Ranges and A. Shrikhande, Bioorg. Med. Chem. Lett., 10, 2051 (2000); doi:10.1016/S0960-894X(00)00272-9.
A. El Kihel, M. Ahbala, T. Harjane, E.M. Essassi and P. Bauchat, Phys. Chem. News, 34, 85 (2007).
A. El Kihel, A. Lagnaoui, T. Harjane, Y. Kattir, S. Guesmi and P. Bauchat, Arabian J. Chem., 6, 173 (2013); doi:10.1016/j.arabjc.2010.09.032.
M. El Ouar, N. Knouzi, A. El Kihel, E.M. Essassi, M. Benchidmi, J. Hamelin, R. Carrié and R. Danion-Bougot, Synth. Commun., 25, 1601 (1995); doi:10.1080/00397919508015844.
A. Errossafi, A. El Kihel, S. Guesmi, M. Saadi and L. El Ammari, Acta Crystallogr., E71, o684 (2015); doi:10.1107/S2056989015015054.
Abdel-Rahman and A.H. Farghaly, J. Chin. Chem. Soc., 51, 147 (2004); doi:10.1002/jccs.200400023.
S. Hiremath, A. Ullagaddi, K. Sekhar and M.G. Purohit, Indian J. Chem., 27B, 758 (1988).
Farhanullah, A. Sharon, P.R. Maulik and V. Ji Ram, Tetrahedron Lett., 45, 5099 (2004); doi:10.1016/j.tetlet.2004.04.172.
M. Jukic, M. Cetina, G. Pavlovic and V. Rapic, Struct. Chem., 10, 85 (1999); doi:10.1023/A:1022077012526.
N.M. Przheval’skii, N.S. Skvortsova and I.V. Magedov, Chem. Heterocycl. Compd., 40, 1435 (2004); doi:10.1007/s10593-005-0061-3.
A. El Kihel, M. Ahbala, A. Mouzdahir, N. Snader, E. Mokhtar Essassi, P. Bauchat and R. Danion-Bougot, Synth. Commun., 38, 200 (2008); doi:10.1080/00397910701738933.