UPDATES
Long Wang et al.
2-Phenyl-3-propyl-4(3H)-quinazolinone (3a): White solid;
mp 99–1018C (Lit.[28] mp 98–1008C); 1H NMR (CDCl3,
600 MHz): d=8.34 (d, J=7.8 Hz, 1H, Ar-H), 7.77–7.73 (m,
2H, Ar-H), 7.52–7.49 (m, 6H, Ar-H), 3.95 (t, J=7.8 Hz, 2H,
NCH2), 1.67–1.61 (m, 2H, CH2), 0.77 (t, J=7.2 Hz, 3H,
CH3); 13C NMR (CDCl3, 100 MHz): d=161.9, 156.1, 147.0,
135.4, 134.1, 129.6, 128.6, 127.6, 127.2, 126.8, 126.6, 120.7,
47.3, 21.9, 11.0.
3-Methyl-2-phenyl-4(3H)-quinazolinone (3b): White solid;
mp 130–1328C (Lit.[29] mp 130–1328C); 1H NMR (CDCl3,
600 MHz): d=8.33 (d, J=7.8 Hz, 1H, Ar-H), 7.75–7.73 (m,
2H, Ar-H), 7.57–7.48 (m, 6H, Ar-H), 3.49 (s, 3H, CH3);
13C NMR (CDCl3, 100 MHz): d=162.3, 155.8, 146.9, 135.1,
133.9, 129.7, 128.5, 127.7, 127.1, 126.6, 126.3, 120.1, 33.9.
3-Isopropyl-2-phenyl-4(3H)-quinazolinone (3c): White
solid; mp 139–1418C (Lit.[30] mp 133–1358C); 1H NMR
(CDCl3, 600 MHz): d=8.31 (d, J=8.4 Hz, 1H, Ar-H), 7.75–
7.70 (m, 2H, Ar-H), 7.52–7.48 (m, 6H, Ar-H), 4.37–4.31 (m,
1H, NCH), 1.59 (d, J=7.2 Hz, 6H, 2CH3); 13C NMR
(CDCl3, 100 MHz): d=162.3, 156.4, 146.6, 136.2, 133.9,
129.5, 128.7, 128.6, 127.0, 126.7, 126.2, 121.9, 53.8, 19.4.
137.5, 134.2, 129.7, 129.0, 127.8, 126.7, 126.4, 126.3, 120.4,
24.1.
7-Chloro-2-phenyl-3-propyl-4(3H)-quinazolinone
(3i):
1
White solid; mp 96–978C; H NMR (CDCl3, 600 MHz): d=
8.25 (d, J=9.0 Hz, 1H, Ar-H), 7.72 (s, 1H, Ar-H), 7.53–7.44
(m, 6H, Ar-H), 3.93 (t, J=7.8 Hz, 2H, NCH2), 1.66–1.60 (m,
2H, CH2), 0.76 (t, J=7.2 Hz, 3H, CH3); 13C NMR (CDCl3,
100 MHz): d=161.4, 157.4, 148.0, 140.3, 135.1, 129.9, 128.7,
128.2, 127.6, 127.4, 126.8, 119.2, 47.5, 21.9, 11.0; HR-MS:
m/z=299.0952, calculated for [C17H15ClN2O+H]+: 299.0951.
7-C hloro-3-methyl-2-phenyl-4(3H)-quinazolinone (3j):
White solid; mp 166–1688C; 1H NMR (CDCl3, 600 MHz):
d=8.26 (d, J=8.4 Hz, 1H, Ar-H), 7.74 (s, 1H, Ar-H), 7.57–
7.44 (m, H, Ar-H), 3.49 (s, 3H, CH3); 13C NMR (CDCl3,
100 MHz): d=161.9, 157.2, 148.1, 140.3, 134.9, 130.2, 128.8,
128.0, 127.8, 127.4, 126.9, 118.8, 34.2; HR-MS: m/z=
271.0633, calculated for [C15H11ClN2O+H]+: 271.0638.
3-Chloro-7,8,9,10-tetrahydroazepinoACTHNUTRGNEUNG[2,1-b]quinazolin-
12(6H)-one (3k):White solid; mp 111–1138C (Lit.[32] mp
101–1048C); 1H NMR (CDCl3, 600 MHz): d=8.17 (d, J=
8.4 Hz, 1H, Ar-H), 7.60 (s, 1H, Ar-H), 7.38 (d, J=8.4 Hz,
1H, Ar-H), 4.37 (t, J=4.2 Hz, 2H, NCH2), 3.06 (t, J=
5.4 Hz, 2H, CH2), 1.88–1.77 (m, 6H, 3CH2); 13C NMR
(CDCl3, 100 MHz): d=160.8, 160.7, 147.9, 139.7, 128.1,
126.5, 125.9, 118.3, 42.6, 37.4, 29.2, 27.6, 24.9.
2-(2-Chlorophenyl)-3-propyl-4(3H)-quinazolinone
(3d):
White solid; mp 114–1168C; 1H NMR (CDCl3, 600 MHz):
d=8.36 (d, J=7.8 Hz, 1H, Ar-H), 7.79–7.74 (m, 2H, Ar-H),
7.54–7.43 (m, 5H, Ar-H), 4.25–4.20 (m, 1H, NCH), 3.49–
3.44 (m, 1H, NCH), 1.73–1.68 (m, 1H, CH), 1.53–1.47 (m,
1H, CH), 0.76 (t, J=7.2 Hz, 3H, CH3); 13C NMR (CDCl3,
100 MHz): d=161.5, 153.2, 146.9, 134.2, 134.0, 132.1, 130.9,
129.6, 129.5, 127.2, 127.1, 127.0, 126.5, 120.9, 46.8, 21.6, 11.0;
HR-MS: m/z=299.0951, calculated for [C17H15ClN2O+H]+:
299.0951.
2,3-Diphenyl-4(3H)-quinazolinone (3l): White solid; mp
158–1608C (Lit.[30] mp 158–1598C); 1H NMR (CDCl3,
600 MHz): d=8.36 (d, J=7.8 Hz, 1H, Ar-H), 7.84–7.80 (m,
2H, Ar-H), 7.55–7.52 (m, 1H, Ar-H), 7.34–7.20 (m, 8H, Ar-
H), 7.15 (d, J=7.8 Hz, 2H, Ar-H); 13C NMR (CDCl3,
100 MHz): d=162.1, 155.0, 147.3, 137.5, 135.2, 134.6, 129.1,
128.9, 128.8, 128.3, 127.8, 127.5, 127.1, 127.0, 120.7.
2-(4-Chlorophenyl)-3-propyl-4(3H)-quinazolinone
(3e):
2-Methyl-3-(ortho-tolyl)-4(3H)-quinazolinone
(3m):
1
White solid; mp 116–1188C (Lit.[33] mp 114–1158C);
1H NMR (CDCl3, 600 MHz): d=8.29 (d, J=8.4 Hz, 1H, Ar-
H), 7.78 (t, J=7.8 Hz, 1H, Ar-H), 7.70 (d, J=8.4 Hz, 1H,
Ar-H), 7.48 (t, J=7.2 Hz, 1H, Ar-H), 7.41–7.38 (m, 3H, Ar-
H), 7.16 (d, J=7.8 Hz, 1H, Ar-H), 2.19 (s, 3H, CH3), 2.13 (s,
3H, CH3); 13C NMR (CDCl3, 100 MHz): d=161.4, 154.1,
147.4, 136.6, 135.1, 134.4, 131.3, 129.4, 127.7, 127.5, 126.9,
126.6, 126.4, 120.5, 23.7, 17.2.
White solid; mp 72–748C; H NMR (CDCl3, 600 MHz): d=
8.33 (d, J=7.8 Hz, 1H, Ar-H), 7.78–7.70 (m, 2H, Ar-H),
7.53–7.48 (m, 5H, Ar-H), 3.94 (t, J=7.8 Hz, 2H, NCH2),
1.65–1.60 (m, 2H, CH2), 0.79 (t, J=7.2 Hz, 3H, CH3);
13C NMR (CDCl3, 100 MHz): d=161.8, 154.9, 146.8, 135.8,
134.2, 133.8, 129.1, 128.9, 127.2, 127.0, 126.6, 120.7, 47.3,
21.9, 11.0; HR-MS: m/z=299.0946, calculated for
[C17H15ClN2O+H]+: 299.0951.
2,3-Dihydropyrrolo
[2,1-b]quinazolin-9(1H)-one
(3n):
7,8,9,10-TetrahydroazepinoACTHNUTRGENUGN[2,1-b]quinazolin-12(6H)-one
(3f): White solid; mp 96–978C (Lit.[31] mp 95–978C);
1H NMR (CDCl3, 600 MHz): d=8.26 (dd, J=7.8 Hz, 1H,
Ar-H), 7.73–7.43 (m, 3H, Ar-H), 4.42–4.38 (m, 2H, NCH2),
3.08 (t, J=5.4 Hz, 2H, CH2), 1.89–1.82 (m, 6H, 3CH2);
13C NMR (CDCl3, 100 MHz): d=161.4, 159.4, 146.8, 133.7,
126.6, 126.2, 126.0, 119.8, 42.5, 37.2, 29.2, 27.7, 25.0.
3-Propyl-2-(para-tolyl)-4(3H)-quinazolinone (3g): White
1
solid; mp 104–1058C; H NMR (CDCl3, 600 MHz): d=8.32
Preparation of the Natural Product (S)-Vasicinone
(7)
To a solution of azide 5[23] (0.72 g, 2 mmol) in toluene
(10 mL) was added Ph3P (0.026 g, 0.1 mmol). After the reac-
(d, J=7.2 Hz, 1H, Ar-H), 7.75–7.72 (m, 2H, Ar-H), 7.51–
7.31 (m, 5H, Ar-H), 3.96 (t, J=7.8 Hz, 2H, NCH2), 2.44 (s,
3H, CH3), 1.66–1.62 (m, 2H, CH2), 0.78 (t, J=7.8 Hz, 3H,
CH3); 13C NMR (CDCl3, 100 MHz): d=161.9, 156.1, 146.9,
139.5, 133.9, 132.5, 129.1, 127.4, 127.1, 126.5, 126.4, 120.6,
47.2, 21.8, 21.2, 10.9; HR-MS: m/z=279.1505, calculated for
[C18H18N2O+H]+: 279.1497.
2-Methyl-3-phenyl-4(3H)-quinazolinone (3h): White solid;
mp 149–1518C (Lit.[28] mp 147–1498C); 1H NMR (CDCl3,
600 MHz): d=8.28 (d, J=7.8 Hz, 1H, Ar-H), 7.78–7.46 (m,
6H, Ar-H), 7.27 (d, J=8.4 Hz, 2H, Ar-H), 2.25 (s, 3H,
CH3); 13C NMR (CDCl3, 100 MHz): d=161.9, 153.9, 147.1,
tion mixture had been stirred for 10 min, TiACTHNURGTNEUNG(O-i-Pr)4
(0.053 g, 0.2 mmol) and TMDS (0.54 g, 4 mmol) was added
sequentially. The reaction mixture was stirred at 1108C and
monitored by TLC. After the reaction was completed
(24 h), the solvent was removed under reduced pressure and
the residue was purified by flash chromatography on silica
gel (ether/petroleum ether=1:4 v/v) to give 4(3H)-quinazo-
linone 6.
1102
ꢁ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2014, 356, 1098 – 1104