ꢁꢀꢀꢀ
ꢂ5
R. Khanivar and A. Zare: Effectual synthesis of 4,6-diarylpyrimidin-2(1H)-onesꢂ
Table 3:ꢀComparison of the results and reaction conditions of [TMEDSA][HSO4]2 with the reported catalysts.
Catalyst
Conditions
Time range
Yield range, %
Ref.
[TMEDSA][HSO4]2
Concentrated HCl
Bi(TFA)3
Large-pore zeolites
Atomized sodium
H6P2W18O62ꢁ·ꢁ18H2O
Sulfamic acid
SBA-Pr-SO3H
NaOH
Solvent-free, 80°C
[bmim][BF4]a, 120°C
15–35
210–300
80–160
20–30
10–15
4–10
15–60
20–40
10–15
360
12–15
10–15
10
15–25
5–15
8–12
79–95
70–95
60–96
76–85c
86–90c
90–95c
90–99c
91–97c
80–92c
25–47c
64–94
74–93
62–94
90–95c
90–96c
90–96c
This work
[24]
[25]
[26]
[27]
[28]
[29]
[30]
[31]
[32]
[33]
[33]
[34]
[35]
[36]
[37]
b
[nbpy]FeCl4 , 70°C
Toluene, reflux
THF, ultrasound, r. t.
Solvent-free, 70°C
Solvent-free, 70°C
Solvent-free, 110°C
Solvent-free, 70°C
2-Propanol, r. t.
Concentrated HCl
TCTd-Zn(OTf)2
TCTd-Bi(OTf)3
HBF4-SiO2
Solvent-free, microwave
Solvent-free, microwave
Solvent-free, microwave
Solvent-free, 70°C
Solvent-free, 80°C
Solvent-free, microwave
H3PMo12O40
I2
DBUe
a1-Butyl-3-methylimidazolium tetrafluroroborate; bn-Butylpyridinium tetrachloroferrate; cIn this work, arylaldehydes bearing electron-
withdrawing substituents (e.g. nitro groups) have not been applied; d2,4,6-trichloro-1,3,5-triazine; e1,8-diazabicyclo[5,4,0]undec-7-ene.
[9] S. Choudhary, K. Pandey, S. Budania, A. Kumar, Mol. Divers.
2017, 21, 155.
[10] M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare,
V. Khakyzadeh, Appl. Catal. A Gen. 2011, 400, 70.
[11] M. A. Zolfigol, M. Zarei, A. Zare, J. Afsar, Appl. Catal. A: Gen.
2015, 505, 224.
[12] F. Tamaddon, D. Azadi, J. Mol. Liq. 2018, 249, 789.
[13] J. Safaei-Ghomi, S. H. Nazemzadeh, H. Shahbazi-Alavi,
Z. Naturforsch. 2017, 72b, 927.
DMSO, 25°C, TMS): δꢁ=ꢁ55.6, 99.5, 113.5, 114.4, 124.9, 127.9,
128.2, 128.9, 130.1, 132.1, 133.1, 162.8, 164.2 [30].
4.2.1.3 4-(4-Chlorophenyl)-6-phenylpyrimidin-2(1H)-one
(1g)
1H NMR (250 MHz, [D6]DMSO, 25°C, TMS): δꢁ=ꢁ7.52–7.65 (m,
6H, HAr and CH), 8.12–8.22 (m, 5H, HAr and NH). – 13C NMR
(62.5 MHz, [D6]DMSO, 25°C, TMS): δꢁ=ꢁ100.9, 127.8, 128.8, [14] M. Leonardi, M. Villacampa, J. C. Menéndez, J. Org. Chem.
2017, 82, 2570.
128.9, 129.7, 132.0, 132.9, 133.4, 136.8, 164.2, 164.5 [29].
[15] S. Mondal, D. Roy, M. K. Jaiswal, G. Panda, Tetrahedron Lett.
2018, 59, 89.
Acknowledgement: The authors are thankful to Payame
[16] A. A. Marzouk, A. A. Abdelhamid, S. K. Mohamed, J. Simpson,
Noor University for the support for this work.
Z. Naturforsch. 2017, 72b, 23.
[17] C. Morozzi, O. Rosati, M. Curini, D. Lanari, Synlett 2018, 29, 126.
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S. Furuya, M. Fujino, J. Med. Chem. 2003, 46, 113.
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C. Spadafora, G. Sbardella, J. Med. Chem. 2005, 48, 6776.
[20] C. J. Shishoo, V. S. Shirsath, I. S. Rathod, V. P. Yande, Eur. J.
Med. Chem. 2000, 35, 351.
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