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. 2018 Nov 9;23(11):2925. doi: 10.3390/molecules23112925

Table 1.

Synthesis of quinazolin-4(3H)-ones.

graphic file with name molecules-23-02925-i001.jpg

Substrate Product R Method a Yield (%)
graphic file with name molecules-23-02925-i002.jpg graphic file with name molecules-23-02925-i003.jpg a: Me
b: Et
c: Pr
d: P
he: H		 1
1
1
1
1		 92
89
93
81
87
graphic file with name molecules-23-02925-i004.jpg graphic file with name molecules-23-02925-i005.jpg a: Me
b: Et
c: Pr
d: Ph		 2
2
2
2		 90
91
ND b
84
graphic file with name molecules-23-02925-i006.jpg graphic file with name molecules-23-02925-i007.jpg a: Me
b: Et
c: Pr
d: Ph		 2
2
2
1(2)		 92
92
88
33(97)
graphic file with name molecules-23-02925-i008.jpg graphic file with name molecules-23-02925-i009.jpg a: Me
b: Et
c: Pr
d: Ph		 2
2
2
1(2)		 94
93
89
7(98)
graphic file with name molecules-23-02925-i010.jpg graphic file with name molecules-23-02925-i011.jpg a: Me
b: Et
c: Pr
d: Ph		 1(2)
1(2)
1(2)
1(2)		 71(86)
70(92)
55(87)
68(80)
graphic file with name molecules-23-02925-i012.jpg graphic file with name molecules-23-02925-i013.jpg a: Me
b: Et
c: Pr
d: Ph		 2
2
2
2		 87
83
ND b
89
graphic file with name molecules-23-02925-i014.jpg graphic file with name molecules-23-02925-i015.jpg a: Me
b: Et
c: Pr
d: Ph		 2
2
2
2		 95
92
ND b
95
graphic file with name molecules-23-02925-i016.jpg graphic file with name molecules-23-02925-i017.jpg a: Me
b: Et
c: Pr
d: Ph		 1(2)
2
2
2		 21(82)
80
ND b
95

a For 1 equiv of the 2-aminobenzamide: Method 1: 1.5 equiv of orthoester, 2 equiv of AcOH, 3 mL of EtOH, 78 °C, 12–24 h; Method 2: 2–3 equiv of orthoester, 3 equiv of AcOH, 3 mL of EtOH, 110 °C, pressure tube, 12–72 h; b ND = not done; c Prepared from 2-nitrobenzoic acid as described in the experimental section.