The Journal of Organic Chemistry
Note
8.60−8.64 (m, 2H), 8.05 (d, J = 8.8 Hz, 1H), 7.89 (t, J = 7.6 Hz, 2H),
7.59 (t, J = 8.0, 7.6 Hz, 1H), 7.17−7.22 (m, 2H); 13C NMR (100
MHz, CDCl3) δ 165.9, 163.4, 160.5, 160.1, 150.7, 134.22, 134.19,
134.15, 130.69, 130.60, 128.5, 127.2, 127.1, 123.5, 115.6, 115.4; MS
m/z (relative intensity) 224 (100), 223 (27.9), 197 (52.6), 170 (5.6),
112 (5.3), 76 (10.0).
intensity) 232 (39.3), 231 (100), 204 (8.5), 128 (4.4), 115 (8.1), 102
(7.8), 77 (3.5).
2-tert-Butylquinazoline (3k): yellow oil; 1H NMR (400 MHz,
CDCl3) δ 9.36 (s, 1H), 7.99 (m, 1H), 7.83−7.87 (m, 2H), 7.57
(m, 1H), 1.52 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 173.5, 159.9,
150.2, 133.5, 128.4, 126.8, 126.7, 122.8, 39.6, 29.6; MS m/z (relative
intensity) 186 (33.1), 185 (15.3), 171 (100), 144 (29.3), 103 (11.4),
77 (7.6), 57 (7.4).
2-(4-Nitrophenyl)quinazoline (3c): yellow solid; mp 218−219 °C
(lit.9 mp 218−219 °C); 1H NMR (400 MHz, CDCl3) δ 9.52 (s, 1H),
8.81−8.43 (m, 2H), 8.36−8.39 (m, 2H), 8.14 (t, J = 8.4, 0.8 Hz, 1H),
7.96−8.01 (m, 2H), 7.69−7.73 (m, 1H); 13C NMR (100 MHz,
CDCl3) δ 160.7, 158.8, 150.6, 149.2, 143.8, 134.6, 129.4, 128.9, 128.3,
127.2, 123.9, 123.7; MS m/z (relative intensity) 252 (39.3), 251 (100),
205 (58.5), 115 (8.0), 102 (7.8), 77 (3.5).
2-Propylquinazoline (3l): yellow oil; 1H NMR (400 MHz, CDCl3)
δ 9.35 (s, 1H), 7.98 (d, J = 8.8 Hz, 1H), 7.85−7.90 (m, 2H), 7.58 (m,
1H), 3.11 (t, J = 7.6 Hz, 2H), 1.97 (m, 2H), 1.05 (t, J = 7.6 Hz, 3H);
13C NMR (100 MHz, CDCl3) δ 167.7, 160.3, 150.3, 133.9, 127.9, 127.0,
126.8, 123.0, 41.8, 22.2, 13.9; MS m/z (relative intensity) 172 (15.6),
161 (100), 157 (23.4), 144 (47.8), 132 (51.0), 118 (23.0), 77 (10.9).
2-(Furan-2-yl)quinazoline (3m): brown solid; mp 131−132 °C (lit.9
2-Phenylquinazoline (3d): pale yellow solid; mp 97−98 °C (lit.9
1
mp 97−98 °C); H NMR (400 MHz, CDCl3) δ 9.46 (s, 1H), 8.62
1
mp 131−132 °C); H NMR (400 MHz, CDCl3) δ 9.38 (s, 1H), 8.09
(dd, J = 8.0 Hz, J = 2.0 Hz, 2H), 8.08 (d, J = 8.4 Hz, 1H), 7.88−7.92
(m, 2H), 7.50−7.62 (m, 4H); 13C NMR (100 MHz, CDCl3) δ 161.0,
160.4, 150.7, 138.0, 134.0, 130.6, 128.6, 128.5, 127.2, 127.1, 123.5; MS
m/z (relative intensity) 207 (17.7), 206 (100), 205 (35.0), 179 (54.4),
103 (18.5), 76 (15.2).
(d, J = 9.2 Hz, 1H), 7.87−7.91 (m, 2H), 7.69 (t, J = 0.8, 0.8 Hz, 1H),
7.57−7.61 (m, 1H), 7.46 (dd, J = 2.8, 0.8 Hz, 1H), 6.63 (dd, J = 3.6, 1.6
Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 160.7, 154.1, 152.5, 150.4,
145.3, 134.4, 128.4, 127.0, 123.3, 114.0, 112.3; MS m/z (relative inten-
sity) 196 (100), 195 (25.4), 168 (23.3), 114 (10.6), 98 (7.3), 76 (6.8).
2-p-Tolylquinazoline (3e): yellow solid; mp 107−109 °C (lit.9 97−
98 °C); 1H NMR (400 MHz, CDCl3) δ 9.43 (s, 1H), 8.51 (d, J = 8.0
Hz, 2H), 8.06 (d, J = 8.4 Hz, 1H), 7.88 (t, J = 8.4, 7.6 Hz, 2H), 7.57 (t,
J = 8.0, 7.6 Hz, 1H), 7.34 (d, J = 8.0 Hz, 2H), 2.44 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ 161.1, 160.4, 150.7, 140.8, 135.3, 134.0, 129.4,
128.50, 128.48, 127.07, 126.97, 123.5, 21.5; MS m/z (relative
intensity) 220 (100), 219 (42.8), 193 (22.0), 165 (9.0), 116 (4.6),
109 (8.0), 91 (5.2), 76 (3.8).
2-(Pyridin-3-yl)quinazoline (3n): yellow solid; mp 94−96 °C (lit.6
c
94−96 °C); 1H NMR (400 MHz, CDCl3) δ 9.82 (s, 1H), 9.46 (s, 1H),
8.46 (d, J = 7.6 Hz, 1H), 8.74 (d, J = 4.8 Hz, 1H), 8.09 (d, J = 8.4 Hz,
1H), 7.93 (t, J = 8.0, 7.6 Hz, 2H), 7.64 (t, J = 7.6, 7.6 Hz, 1H), 7.45
(dd, J = 8.0, 4.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 160.6,
159.1, 151.2, 150.6, 150.2, 135.7, 134.3, 133.5, 128.6, 127.7, 127.1,
123.7, 123.3; MS m/z (relative intensity) 208 (14.8), 207 (100), 179
(29.0), 153 (6.1), 129 (2.9), 103 (7.2), 76 (11.2), 50 (6.4).
6-Chloro-2-(4-methoxyphenyl)quinazoline (3o): yellow solid; mp
168−169 °C; 1H NMR (400 MHz, CDCl3) δ 9.33 (s, 1H), 8.55 (d, J =
8.8 Hz, 2H), 7.97(d, J = 9.2 Hz, 1H), 7.86 (d, J = 1.0 Hz, 1H), 7.80
(dd, J = 8.8, 1.0 Hz, 1H), 7.03 (d, J = 8.8 Hz, 2H), 3.90 (s, 3H);
13C NMR (100 MHz, CDCl3) δ 162.0, 161.1, 159.4, 149.3, 134.9,
132.2, 130.3, 130.25, 130.15, 125.8, 123.7, 114.0, 55.4; MS m/z
(relative intensity) 272 (29.7), 270 (100), 255 (20.0), 227 (11.9), 194
(15.2), 149 (14.1), 106 (11.7), 71 (12.7), 57 (13.0); ESI-HRMS m/z
calcd for C15H11ClN2O + H+ 271.0633, found 271.0637.
2-(4-Methoxyphenyl)quinazoline (3f): white solid; mp 91−93 °C
9
1
(lit. mp 90−91 °C); H NMR (400 MHz, CDCl3) δ 9.41 (s, 1H),
8.58 (dd, J = 7.2, 2.0 Hz, 2H), 8.03 (d, J = 8.4 Hz, 1H), 7.87 (t, J = 8.4,
7.6 Hz, 2H), 7.56 (t, J = 7.6, 7.2 Hz, 1H), 7.03 (dd, J = 7.2, 2.0 Hz, 2H),
3.90 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 161.8, 160.9, 160.4, 150.8,
134.0, 130.7, 130.2, 128.4, 127.1, 126.8, 123.3, 114.0, 55.4; MS m/z
(relative intensity) 236 (100), 235 (19.6), 221 (18.1), 209 (10.6), 193
(12.1), 166 (9.5), 118 (4.4), 97 (4.2), 90 (3.8), 77 (4.1).
2-(3-Bromophenyl)quinazoline (3g): yellow solid; mp 153−155 °C;
1H NMR (400 MHz, CDCl3) δ 9.43 (s, 1H), 8.78 (s, 1H), 8.54 (d, J =
8.0 Hz, 1H), 8.07 (d, J = 8.8 Hz, 1H), 7.89−7.92 (m, 2H), 7.60−7.63
(m, 2H), 7.39 (t, J = 8.0, 8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ
160.5, 159.5, 150.6, 140.0, 134.2, 133.4, 131.5, 130.1, 128.6, 127.6,
127.10, 127.06, 123.7, 122.9; MS m/z (relative intensity) 286 (97.7),
284 (100), 257 (18.1), 205 (42.9), 178 (46.4), 151 (19.0), 102 (33.4),
76 (19.2), 50 (19.1). ESI-HRMS m/z calcd for C14H9BrN2 + H+
285.0022, found:285.0025.
2-(3-Chlorophenyl)quinazoline (3h): pale yellow solid; mp 148−
150 °C; 1H NMR (400 MHz, CDCl3) δ 9.46 (s, 1H), 8.63 (t, J = 0.8,
1.2 Hz, 1H), 8.50−8.53 (m, 1H), 8.08 (dd, J = 8.4, 0.8 Hz, 1H), 7.90−
7.94 (m, 2H), 7.62−7.66 (m, 1H), 7.44−7.49 (m, 2H); 13C NMR
(100 MHz, CDCl3) δ 160.5, 159.7, 150.7, 139.9, 134.8, 134.3, 130.5,
129.8, 128.69, 128.66, 127.6, 127.1, 126.6, 123.8; MS m/z (relative
intensity) 242 (33.3), 240 (100), 239 (20.4), 213 (30.4), 178 (41.1),
151 (11.0), 120 (10.9), 102 (28.3), 76 (14.9); ESI-HRMS m/z Calcd
for C14H9ClN2 + H+ 241.0527, found 241.0526.
6-Chloro-2-(4-chlorophenyl)quinazoline (3p): yellow solid; mp
207−209 °C; 1H NMR (400 MHz, CDCl3) δ 9.38 (s, 1H), 8.55 (d, J =
8.4 Hz, 2H), 8.02 (d, J = 9.2 Hz, 1H), 7.91 (d, J = 2.4 Hz, 1H), 7.85
(dd, J = 9.2, 2.4 Hz, 1H), 7.49 (d, J = 8.4 Hz, 2H); 13C NMR (100
MHz, CDCl3) δ 160.3, 159.6, 149.2, 137.2, 136.1, 135.2, 133.0, 129.9,
128.9, 125.8, 124.0; MS m/z (relative intensity) 278 (12.5), 276
(63.2), 274 (100), 247 (28.0), 214 (9.9), 212 (9.9), 177 (26.4), 106
(30.1), 75 (20.6), 57 (15.6); ESI-HRMS m/z calcd for C14H8Cl2N2 +
H+ 275.0137, found 275.0133.
2-(4-Methoxyphenyl)-6-methylquinazoline (3q): yellow solid; mp
118−120 °C; 1H NMR (400 MHz, CDCl3) δ 9.31 (s, 1H), 8.55 (d, J =
8.8 Hz, 2H), 7.93 (d, J = 8.8 Hz, 1H), 7.70 (d, J = 8.4 Hz, 1H), 7.64 (s,
1H), 7.04 (d, J = 8.8 Hz, 2H), 3.89 (s, 3H), 2.54 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ 161.6, 160.2, 159.6, 149.4, 136.9, 136.3, 130.8,
130.0, 128.0, 125.8, 123.3, 113.9, 55.4, 21.6; MS m/z (relative
intensity) 250 (100), 249 (14.1), 223 (21.3), 207 (11.3), 180 (6.7),
103 (7.0), 77 (2.3); ESI-HRMS m/z calcd for C16H14N2O + H+
251.1179, found 251.1181.
2-(2-Chlorophenyl)quinazoline (3i): yellow solid; mp 69−70 °C;
1H NMR (400 MHz, CDCl3) δ 9.36 (s, 1H), 8.13 (d, J = 8.4 Hz, 1H),
7.94−8.01 (m, 2H), 7.82−7.85 (m, 1H), 7.70 (t, J = 8.0, 7.2 Hz, 1H),
7.53−7.57 (m, 1H), 7.39−7.46 (m, 2H); 13C NMR (100 MHz,
CDCl3) δ 161.8, 160.1, 150.2, 138.2, 134.2, 132.8, 131.7, 130.4, 130.2,
128.5, 127.9, 127.0, 126.7, 123.1; MS m/z (relative intensity) 242
(22.4), 240 (66.3), 213 (16.9), 205 (100), 178 (31.0), 177 (11.0), 151
(10.6), 120 (9.8), 102 (19.3), 76 (13.4); ESI-HRMS m/z calcd for
C14H9ClN2 + H+ 241.0527, found 241.0527.
6-Methyl-2-(pyridin-3-yl)quinazoline (3r): yellow solid; mp 140−
1
142 °C; H NMR (400 MHz, CDCl3) δ 9.79 (s, 1H), 9.38 (s, 1H),
8.83 (m, 1H), 8.73 (dd, J = 4.8, 1.2 Hz, 1H), 7.99 (d, J = 8.8 Hz, 1H),
7.77 (dd, J = 8.8, 1.6 Hz, 1H), 7.70 (s, 1H), 7.45 (dd, J = 8.0, 4.8 Hz,
1H), 2.51 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 159.9, 158.5,
151.0, 150.1, 149.2, 138.0, 136.7, 135.6, 133.6, 128.3, 125.8, 123.8,
123.3, 21.7; MS m/z (relative intensity) 221 (100), 220 (46.6), 194
(18.8), 179 (6.6), 110 (7.6), 89 (17.7), 78 (3.3), 40 (8.7); ESI-HRMS
m/z calcd for C14H11N3 + H+ 222.1026, found: 222.1023.
(E)-2-Styrylquinazoline (3j): white solid; mp 120−121 °C (lit.9 mp
120−121 °C); 1H NMR (400 MHz, CDCl3) 9.37 (s, 1H), 8.17 (d, J =
15.6 Hz, 1H), 8.00 (d, J = 8.0 Hz, 1H), 7.86−7.90 (m, 2H), 7.68 (d,
J = 7.2 Hz, 2H), 7.56−7.60 (m, 1H), 7.34−7.44 (m, 4H); 13C NMR
(100 MHz, CDCl3) δ 161.3, 160.2, 150.6, 138.5, 136.2, 134.2, 129.0,
128.8, 128.2, 128.0, 127.7, 127.2, 127.1, 123.4; MS m/z (relative
2-(4-Chlorophenyl)-4H-benzo[d][1,3]oxazine (7a): white solid; mp
132−133 °C; 1H NMR (400 MHz, CDCl3) δ 8.08 (d, J = 8.8 Hz, 2H),
7.40 (d, J = 8.8 Hz, 2H), 7.29−7.33 (m, 1H), 7.26 (m, 1H), 7.18 (m,
1H), 7.00 (d, J = 7.2 Hz, 1H), 5.38 (s, 2H); 13C NMR (100 MHz,
CDCl3) δ 156.7, 139.4, 137.6, 130.9, 129.0, 129.3, 129.0, 126.6, 124.7,
1140
dx.doi.org/10.1021/jo2020399 | J. Org. Chem. 2012, 77, 1136−1142