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One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-thione Derivatives Using DBU as Green and Recyclable Catalyst
Corresponding Author(s) : P. Thriveni
Asian Journal of Chemistry,
Vol. 30 No. 6 (2018): Vol 30 Issue 6
Abstract
A short and simple one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-thione derivatives was accomplished in excellent yields by reaction of aryl ketone, aryl aldehydes and thiourea in aqueous ethanol (50 %) using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a reusable catalyst.
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- N.C. Desai, D.D. Pandya, H.M. Satodiya, K.M. Rajpara, V.V. Joshi and H.V. Vaghani, Med. Chem. Res., 21, 4412 (2012); https://doi.org/10.1007/s00044-012-9980-6.
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- M.A. El-Hashash, M.R. Mahmoud and S.A. Madboli, Indian J. Chem., 32B, 449 (1993).
- D.J. Brown, The Chemistry of Heterocyclic Compounds: The Pyrimidines, Wiley, New York, USA, vol. 52 (1994).
- J. Safaei-Ghomi and M.A. Ghasemzadeh, Org. Prep. Proced. Int., 44, 527 (2012); https://doi.org/10.1080/00304948.2012.730944.
- R. Gupta and R.P. Chaudhary, Heterocycl. Commun., 19, 207 (2013); https://doi.org/10.1515/hc-2013-0024.
- J. Safaei-Ghomi and A. Ghasemzadeh, J. Serbian Chem. Soc., 76, 679 (2011); https://doi.org/10.2298/JSC100212057S.
- B.F. Abdel-Wahab and H.A. Mohamed, Phosphorus Sulfur Silicon Rel. Elem., 192, 787 (2017); https://doi.org/10.1080/10426507.2017.1290630.
- A.O. Abdelhamid, Z.H. Ismail, M.S. El-Gendy and M.M. Ghorab, Phosphorus Sulfur Silicon Rel. Elem., 182, 2409 (2007); https://doi.org/10.1080/10426500701501292.
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- N.R. Candeias, L.C. Branco, P.M.P. Gois, C.A.M. Afonso and A.F. Trindade, Chem. Rev., 109, 2703 (2009); https://doi.org/10.1021/cr800462w.
- V.A. Chebanov, V.E. Saraev, S.M. Desenko, V.N. Chernenko, S.V. Shishkina, O.V. Shishkin, K.M. Kobzar and C.O. Kappe, Org. Lett., 9, 1691 (2007); https://doi.org/10.1021/ol070411l.
- K.-H. Kong, Y. Chen, X. Ma, W.K. Chui and Y. Lam, J. Comb. Chem., 6, 928 (2004); https://doi.org/10.1021/cc049910t.
- Z.-L. Shen, X.-P. Xu and S.-J. Ji, J. Org. Chem., 75, 1162 (2010); https://doi.org/10.1021/jo902394y.
- H. Kefayati, F. Asghari and R. Khanjanian, J. Mol. Liq., 172, 147 (2012); https://doi.org/10.1016/j.molliq.2012.01.019.
- K. Aswin, S.S. Mansoor, K. Logaiya and S.P.N. Sudhan, J. King Saud Univ. Sci., 26, 141 (2014); https://doi.org/10.1016/j.jksus.2013.05.004.
- M. Kidwai and P. Misra, Synth. Commun., 29, 3237 (1999); https://doi.org/10.1080/00397919908085949.
References
N.C. Desai, D.D. Pandya, H.M. Satodiya, K.M. Rajpara, V.V. Joshi and H.V. Vaghani, Med. Chem. Res., 21, 4412 (2012); https://doi.org/10.1007/s00044-012-9980-6.
A. Zakaria Abdel-Samii. Hanan, A. Abdel-Fattah and Reham M. AbdelRehem, World J. Pharm. Res., 4, 73 (2015).
M.A. El-Hashash, M.R. Mahmoud and S.A. Madboli, Indian J. Chem., 32B, 449 (1993).
D.J. Brown, The Chemistry of Heterocyclic Compounds: The Pyrimidines, Wiley, New York, USA, vol. 52 (1994).
J. Safaei-Ghomi and M.A. Ghasemzadeh, Org. Prep. Proced. Int., 44, 527 (2012); https://doi.org/10.1080/00304948.2012.730944.
R. Gupta and R.P. Chaudhary, Heterocycl. Commun., 19, 207 (2013); https://doi.org/10.1515/hc-2013-0024.
J. Safaei-Ghomi and A. Ghasemzadeh, J. Serbian Chem. Soc., 76, 679 (2011); https://doi.org/10.2298/JSC100212057S.
B.F. Abdel-Wahab and H.A. Mohamed, Phosphorus Sulfur Silicon Rel. Elem., 192, 787 (2017); https://doi.org/10.1080/10426507.2017.1290630.
A.O. Abdelhamid, Z.H. Ismail, M.S. El-Gendy and M.M. Ghorab, Phosphorus Sulfur Silicon Rel. Elem., 182, 2409 (2007); https://doi.org/10.1080/10426500701501292.
D. Zhao, C. Chen, H. Liu, L. Zheng, Y. Tong, D. Qu and S. Han, Eur. J. Med. Chem., 87, 500 (2014); https://doi.org/10.1016/j.ejmech.2014.09.096.
N.R. Candeias, L.C. Branco, P.M.P. Gois, C.A.M. Afonso and A.F. Trindade, Chem. Rev., 109, 2703 (2009); https://doi.org/10.1021/cr800462w.
V.A. Chebanov, V.E. Saraev, S.M. Desenko, V.N. Chernenko, S.V. Shishkina, O.V. Shishkin, K.M. Kobzar and C.O. Kappe, Org. Lett., 9, 1691 (2007); https://doi.org/10.1021/ol070411l.
K.-H. Kong, Y. Chen, X. Ma, W.K. Chui and Y. Lam, J. Comb. Chem., 6, 928 (2004); https://doi.org/10.1021/cc049910t.
Z.-L. Shen, X.-P. Xu and S.-J. Ji, J. Org. Chem., 75, 1162 (2010); https://doi.org/10.1021/jo902394y.
H. Kefayati, F. Asghari and R. Khanjanian, J. Mol. Liq., 172, 147 (2012); https://doi.org/10.1016/j.molliq.2012.01.019.
K. Aswin, S.S. Mansoor, K. Logaiya and S.P.N. Sudhan, J. King Saud Univ. Sci., 26, 141 (2014); https://doi.org/10.1016/j.jksus.2013.05.004.
M. Kidwai and P. Misra, Synth. Commun., 29, 3237 (1999); https://doi.org/10.1080/00397919908085949.