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p-TSA Catalyzed Synthesis of Tetrahydrobenzo[g]quinolines via Multicomponent Reaction using Pyrazole Aldehyde, Lawsone, β-Ketoesters and Ammonium Acetate
Corresponding Author(s) : Manickam Pramesh
Asian Journal of Chemistry,
Vol. 34 No. 6 (2022): Vol 34 Issue 6
Abstract
An efficient protocol has been developed for the multicomponent synthesis of tetrahydrobenzo[g]quinoline-3-carboxylate derivatives using p-toluenesulfonic acid (p-TSA) as catalyst through one-pot four component condensation reaction of pyrazole aldehyde, Lawsone, β-ketoesters and ammonium acetate in ethanol. The synthesized compounds were characterized by spectroscopic techniques.
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- A. Domling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000); https://doi.org/10.1002/1521-3773(20000915)39:18<3168::AIDANIE3168>3.0.CO;2-U
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- M. Pramesh, S. Jayanthi and P. Perumal, Int. J. Adv. Res. (Indore), 2, 345 (2014).
- B. Devi Bala, V. Balamurugan and S. Perumal, Tetrahedron Lett., 52, 4562 (2011); https://doi.org/10.1016/j.tetlet.2011.06.102
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- Z.N. Tisseh and A. Bazgir, Dyes Pigments, 83, 258 (2009); https://doi.org/10.1016/j.dyepig.2008.09.003
- K. Yadav, A. Kumar, A. Kumar, N. Misra and G. Brahmachari, J. Mol. Struct., 1154, 596 (2018); https://doi.org/10.1016/j.molstruc.2017.09.095
- F. Khorami and H.R. Shaterian, Chin. J. Catal., 35, 242 (2014); https://doi.org/10.1016/S1872-2067(12)60761-X
- S. Salunke-Gawali, E. Pereira, U.A. Dar and S. Bhand, J. Mol. Struct., 1148, 435 (2017); https://doi.org/10.1016/j.molstruc.2017.06.130
- H.R. Shaterian and M. Mohammadnia, J. Mol. Liq., 177, 353 (2013); https://doi.org/10.1016/j.molliq.2012.10.012
- R.X. Faria, F.H. Oliveira, J.P. Salles, A.S. Oliveira, N.L. von Ranke, M.L. Bello, C.R. Rodrigues, H.C. Castro, A.R. Louvis, D.L. Martins and V.F. Ferreira, Eur. J. Med. Chem., 143, 1361 (2018); https://doi.org/10.1016/j.ejmech.2017.10.033
- A. Upadhyay, V.K. Singh, R. Dubey, N. Kumar, L.K. Sharma and R.K.P. Singh, Tetrahedron Lett., 58, 4323 (2017); https://doi.org/10.1016/j.tetlet.2017.09.048
- S. Elavarasan and M. Gopalakrishnan, Spectrochim. Acta A Mol Biomol. Spectrosc., 133, 1 (2014); https://doi.org/10.1016/j.saa.2014.05.037
References
A. Domling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000); https://doi.org/10.1002/1521-3773(20000915)39:18<3168::AIDANIE3168>3.0.CO;2-U
W.H. Hamama, E.A. Hassanien and H.H. Zoorob, J. Heterocycl. Chem., 54, 341 (2017); https://doi.org/10.1002/jhet.2589
F. Jafari, H. Baghayi, P. Lavaee, F. Hadizadeh, H. Moallemzadeh, F. Soltani, S. Mirzaei, S.M. Aboutorabzadeh and R. Ghodsi, Eur. J. Med. Chem., 164, 292 (2019); https://doi.org/10.1016/j.ejmech.2018.12.060
E. Maalej, F. Chabchoub, M.J. Oset-Gasque, M. Esquivias-Pérez, M.P. González, L. Monjas, C. Pérez, C. de los Ríos, M.I. Rodríguez-Franco, I. Iriepa, I. Moraleda, M. Chioua, A. Romero, J. Marco-Contelles and A. Samadi, Eur. J. Med. Chem., 54, 750 (2012); https://doi.org/10.1016/j.ejmech.2012.06.038
M.A. Kira, M.N. Aboul Enein and M. Korkor, J. Heterocycl. Chem., 7, 25 (1970); https://doi.org/10.1002/jhet.5570070102
J.V. Faria, P.F. Vegi, A.G.C. Miguita, M.S. dos Santos, N. Boechat and A.M.R. Bernardino, Bioorg. Med. Chem., 25, 5891 (2017); https://doi.org/10.1016/j.bmc.2017.09.035
M. Pramesh and P. Perumal, Int. J. Adv. Res. (Indore), 2, 1151 (2014).
M. Pramesh, S. Jayanthi and P. Perumal, Int. J. Adv. Res. (Indore), 2, 345 (2014).
B. Devi Bala, V. Balamurugan and S. Perumal, Tetrahedron Lett., 52, 4562 (2011); https://doi.org/10.1016/j.tetlet.2011.06.102
T.M. Al-Mutairi, H.M. Al-Hazimi and F.E.M. El-Baih, J. Saudi Chem. Soc., 13, 199 (2009); https://doi.org/10.1016/j.jscs.2009.06.001
S.A. Khan, A.M. Asiri, S.H. Al-Thaqafy, H.M. Faidallah and S.A. ElDaly, Spectrochim. Acta A Mol Biomol. Spectrosc., 133, 141 (2014); https://doi.org/10.1016/j.saa.2014.05.013
D.R. da Rocha, K. Mota, I.M.C.B da Silva, V.F. Ferreira; S.B. Ferreira and F.C. Silva, Tetrahedron, 70, 3266 (2014); https://doi.org/10.1016/j.tet.2013.11.068
B. SathishKumar, K. Ravi, A.K. Verma, K. Fatima, M. Hasanain, A. Singh, J. Sarkar, S. Luqman, D. Chanda and A.S. Negia, Bioorg. Med. Chem., 25, 1364 (2017); https://doi.org/10.1016/j.bmc.2016.12.043
J.F.D. Chabert, G. Chatelaina, S. Pellet-Rostaing, D. Bouchu and M. Lemairea, Tetrahedron Lett., 47, 1015 (2006); https://doi.org/10.1016/j.tetlet.2005.11.108
Z.N. Tisseh and A. Bazgir, Dyes Pigments, 83, 258 (2009); https://doi.org/10.1016/j.dyepig.2008.09.003
K. Yadav, A. Kumar, A. Kumar, N. Misra and G. Brahmachari, J. Mol. Struct., 1154, 596 (2018); https://doi.org/10.1016/j.molstruc.2017.09.095
F. Khorami and H.R. Shaterian, Chin. J. Catal., 35, 242 (2014); https://doi.org/10.1016/S1872-2067(12)60761-X
S. Salunke-Gawali, E. Pereira, U.A. Dar and S. Bhand, J. Mol. Struct., 1148, 435 (2017); https://doi.org/10.1016/j.molstruc.2017.06.130
H.R. Shaterian and M. Mohammadnia, J. Mol. Liq., 177, 353 (2013); https://doi.org/10.1016/j.molliq.2012.10.012
R.X. Faria, F.H. Oliveira, J.P. Salles, A.S. Oliveira, N.L. von Ranke, M.L. Bello, C.R. Rodrigues, H.C. Castro, A.R. Louvis, D.L. Martins and V.F. Ferreira, Eur. J. Med. Chem., 143, 1361 (2018); https://doi.org/10.1016/j.ejmech.2017.10.033
A. Upadhyay, V.K. Singh, R. Dubey, N. Kumar, L.K. Sharma and R.K.P. Singh, Tetrahedron Lett., 58, 4323 (2017); https://doi.org/10.1016/j.tetlet.2017.09.048
S. Elavarasan and M. Gopalakrishnan, Spectrochim. Acta A Mol Biomol. Spectrosc., 133, 1 (2014); https://doi.org/10.1016/j.saa.2014.05.037