ꢁꢀꢀꢀ
H. Kang et al.: Microwave-assisted synthesis of quinazolin-4(3H)-onesꢃ ꢃ3
2-Styryl-quinazolin4-(3H)-one (3g)ꢀThis compound was obtained
in yields of 74% (heat) and 87% (MW); mp 253–255°C (lit. [28] mp
249–250°C).
[4] Mohammadi, A. A.; Ahdenov, R.; Sooki, A. A. Design, syn-
thesis and antibacterial evaluation of 2-alkyl- and 2-aryl-3-
(phenylamino)quinazolin-4(3H)-one derivatives. Heterocycl.
Commun. 2017, 23, 105–108.
2-(2-Furyl)quinazolin-4(3H)-one (3h)ꢀThis compound was
obtained in yields of 69% (heat) and 88% (MW); mp 233–235°C (lit.
[28] mp 219–221°C).
[5] Alagarsamy, V.; Pathak, U. S. Synthesis and antihypertensive
activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]
quinazolin-9-ones. Bioorg. Med. Chem. 2007, 15, 3457–3462.
[6] Kundu, P.; Mondal, A.; Chowdhury, C. A Palladium-catalyzed
method for the synthesis of 2-(α-styryl)-2,3-dihydroquinazolin-
4-ones and 3-(α-styryl)-3,4-dihydro-1,2,4-benzothiadiazine-
1,1-dioxide: access to 2-(α-styryl)quinazolin-4(3H)-ones and
3-(α-styryl)-1,2,4-benzothiadiazine-1,1-dioxides. J. Org. Chem.
2016, 81, 6596–6608.
2-Ethyl-quinazolin-4(3H)-one (3i)ꢀThis compound was obtained
in yields of 72% (heat) and 84% (MW); mp 238–240°C (lit. [32] mp
235–236°C).
2-Propyl-4(3H)-quinazolin-4(3H)-one (3j)ꢀThis compound was
obtained in yields of 70% (heat) and 80% (MW); mp 210–212°C (lit.
[33] mp 208–210°C).
[7] Baghbanzadeh, M.; Dabiri, M.; Saleh, P. A new efficient method
for the three-component synthesis of 4(3H)-quinazolinones.
Heterocyeles 2008, 75, 2809–2815.
2,2-Dimethyl-2,3-dihydroquinazolin-4(1H)-one (5a)ꢀThis com-
pound was obtained in yields of 92% (MW); mp 178–180°C (lit. [34]
mp 183–184°C).
[8] Abe, T.; Kida, K.; Yamada, K. A copper-catalyzed Ritter-type
cascade via iminoketene for the synthesis of quinazolin-4(3H)-
ones and diazocines. Chem. Commun. 2017, 53, 4362–4365.
[9] Parua, S.; Das, S.; Sikari, R.; Paul, N. D. One-pot cascade syn-
thesis of quinazolin-4(3H)-ones via nickel-catalyzed dehydro-
genative coupling of o-aminobenzamides with alcohols. J. Org.
Chem. 2017, 82, 7165–7175.
2-Ethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one
(5b)ꢀThis
compound was obtained in yields of 94% (MW); mp 178–180°C (lit.
[35] mp 184–186°C).
[10] Li, T.; Chen, M.; Yang, L.; Xiong, Z.; Wang, Y.; Li, F.; Chen, D.
Copper-catalyzed consecutive reaction to construct quinazolin-
4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones. Tetrahe-
dron 2016, 72, 868–874.
1′H-spiro[cyclohexane-1,2′-quinazolin]-4′(3′H)-one
(5c)ꢀThis
compound was obtained in yields of 95% (MW); mp 225–226°C (lit.
[35] mp 224–225°C).
[11] Rao, K. R.; Mekala, R.; Raghunadh, A.; Meruva, S. B.; Kumar, S.
P.; Kalita, D.; Laxminarayan, E.; Prasadc, B.; Pal, M. A catalyst-
free rapid, practical and general synthesis of 2-substituted
quinazolin-4(3H)-ones leading to luotonin B and E, bouchar-
datine and 8-norrutaecarpine. RSC Adv. 2015, 5, 61575–61579.
[12] Ren, Z. L.; Kong, H. H.; Lu, W. T.; Sun, M.; Ding, M. W. One-pot
synthesis of quinazolin-4(3H)-ones and fused quinazolinones
by a palladium-catalyzed domino process. Tetrahedron 2018,
74, 184–193.
[13] Oveisi, A. R.; Khorramabadi-Zad, A.; Daliran, S. Iron-based metal-
organic framework, Fe(BTC): An effective dual-functional catalyst
for oxidative cyclization of bisnaphthols and tandem synthesis of
quinazolin-4(3H)-ones. RSC Adv. 2015, 6, 1136–1142.
[14] Yoo, C. L.; Fettinger, J. C.; Kurth, M. J. Stannous Chloride in
alcohol: a one-pot conversion of 2-nitro-N-arylbenzamides to
2,3-dihydro-1H-quinazoline-4-ones. J. Org. Chem. 2005, 70,
6941–6943.
2-Methyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (5d)ꢀThis
compound was obtained in yields of 89% (MW); mp 226–228°C (lit.
[36] mp 225–229°C).
Acknowledgments: This work was financially supported
by the Natural Science Foundation of Shandong Province
(Funder Id: 10.13039/501100007129, No. ZR2017PB006),
the Ph.D. Programs Foundation of Ludong University
(No. 32840301), the National University Student Inno-
vation and entrepreneurship training Program (No.
201710451034, 201810451326, 201810451344) and the
Innovation Foundation Plan of Ludong University (No.
ld171062).
[15] Niu, Y.; Qu, R.; Chen, H.; Mu, L.; Liu, X.; Wang, T.; Zhang, Y.;
Sun, C. Synthesis of silica gel supported salicylaldehyde modi-
fied PAMAM dendrimers for the effective removal of Hg(II) from
aqueous solution. J. Hazard. Mater. 2014, 278, 267–278.
[16] Liu, Y.; Xu, L.; Liu, J.; Liu, X.; Chen, C.; Li, G.; Meng, Y. Graphene
oxides cross-linked with hyperbranched polyethylenimines:
Preparation, characterization and their potential as recycla-
ble and highly efficient adsorption materials for lead(II) ions.
Chem. Eng. J. 2016, 285, 698–708.
[17] Zhang, S.; Zhang, Y.; Liu, J.; Xu, Q.; Xiao, H.; Wang, X.; Xu, H.;
Zhou, J. Thiol modified Fe3O4@SiO2 as a robust, high effective,
and recycling magnetic sorbent for mercury removal. Chem.
Eng. J. 2013, 226, 30–38.
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