Abstract
A highly efficient method has been developed for synthesis of 7,9-disubstituted-6,7-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazolines via multicomponent one-pot two-step tandem reaction involving 1-tetralone, arylaldehydes, thiourea, and 4-chlorophenacyl bromide/(3-bromoacetyl)coumarin utilizing p-toluenesulfonic acid as catalyst in glacial acetic acid under reflux conditions. Analytically pure products are formed with excellent yield and short reaction time. All the synthesized compounds were confirmed by their spectral and elemental analyses.
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S.A. Abdel-Mohsen, J. Chin. Chem. Soc. 50, 1085 (2003)
A.C. Robert, A.G. Richard, F.C. Zdzislaw, J. Med. Chem. 17, 1025 (1974)
S.F. Mohamed, E.M. Flefel, A.E. Amr, D.N. Abd El-Shafy, Eur. J. Med. Chem. 45, 1494 (2010)
S. Maddila, G.L.V. Damu, E.O. Oseghe, O.A. Abafe, C. Venakata Rao, P. Lavanya, J. Korean Chem. Soc. 56, 334 (2012)
E.E. Flefel, M.A. Salama, M. El-Shahat, M.A. El-Hashash, A.F. El-Farargy, Phosphorus Sulfur Silicon Relat. Elem. 182, 1739 (2007)
B. Tozkoparan, M. Ertan, P. Kelicen, R. Demirdamar, Farmaco 54, 588 (1999)
E. Jeanneau-Nicolle, M. Benoit-Guyod, A. Namil, G. Leclerc, Eur. J. Med. Chem. 27, 115 (1992)
E.A. Abd El-Galil, S.S. Maigali, M.M. Abdulla, Monatsh. Chem. 139, 1409 (2008)
K. Danel, E.B. Pedersen, C. Nielsen, J. Med. Chem. 41, 191 (1998)
B. Pan, R. Huang, L. Zheng, C. Chen, S. Han, D. Qu, M. Zhu, P. Wei, Eur. J. Med. Chem. 46, 819 (2011)
A. Balkan, S. Uma, M. Ertan, W. Wiegrebe, Pharmazie 47, 687 (1992)
J. Wichmann, G. Adam, S. Kolczewski, V. Mutel, T. Woltering, Bioorg. Med. Chem. Lett. 9, 1573 (1999)
S. Ruiu, G. Marchese, P.L. Saba, G.L. Gessa, L. Pani, Mol. Psychiatr. 5, 673 (2000)
M.A. Fadi, Sci. Pharm. 76, 415 (2008)
C.N. Khobragade, R.G. Bodade, B.S. Dawane, S.G. Konda, N.T. Khandare, J. Enzyme Inhib. Med. Chem. 25, 615 (2010)
H. Zhi, L.M. Chen, L.L. Zhang, S.J. Liu, D.C.C. Wan, H.Q. Lin, C. Hu, Arkivoc xiii, 266 (2008)
S. Kolb, O. Mondesert, M.-L. Goddard, D. Jullien, B.O. Villoutreix, B. Ducommun, C. Garbay, E. Braud, Chem. Med. Chem. 4, 633 (2009)
M.M. Ghorab, S.M. Abdel-Gawad, M.S. El-Gaby, Farmaco 55, 249 (2000)
B. Janardhan, K. Manjulatha, B. Srinivas, B. Rajitha, N. Muralikrishna, A. Sadanandam, RSC Adv. 4, 22866 (2014)
A.A. Abu-Hashem, M.M. Youssef, H.A.R. Hussein, J. Chin. Chem. Soc. 58, 41 (2011)
B. Janardhan, B. Srinivas, B. Rajitha, A.C. Peter, Tetrahedron Lett. 55, 224 (2014)
J. Zhu, H. Bienayme, Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)
A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)
A. Gursoy, N. Karali, Turk. J. Chem. 27, 545 (2003)
Acknowledgments
The authors would like to thank the Head, Department of Chemistry, Osmania University for providing research facilities. B. Sonyanaik thanks the University Grant Commission (UGC), New Delhi for financial assistance.
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The authors report no conflicts of interest. The authors alone hereby stand responsible for the contents of this scientific paper.
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Sakram, B., Sonyanaik, B., Ashok, K. et al. Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction. Res Chem Intermed 42, 1699–1705 (2016). https://doi.org/10.1007/s11164-015-2112-4
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DOI: https://doi.org/10.1007/s11164-015-2112-4