编辑: 252276522 | 2019-07-13 |
NMR-data was recorded by a Bruker ARX
300 and Bruker ARX
400 spectrometers.
13 C- and
1 H-spectra were referenced to deuterated solvent signals. Peaks were characterized as singlet (s), doublet (d), doublet of doublet (dd), triplet (t), doublet of triplets (dt), quartet (q) and multiplet (m). Gas-chromatographie-mass-analysis was measured by an Agilent HP-5890 with Agilent HP-5973 Mass Selective Detector (EI) and HP-5-capillary column using helium as carrier gas. Column-chromatographie was carried out using Merck
60 Silica-Gel (0.043 - 0.06 mm) and distilled solvents were used. General experimental procedure: 2-Phenyl-2,3-dihydroquinazolin-4(1H)-one
1 H-NMR (250 MHz, DMSO-d6): δ = 8.28 (s, 1H, NH(3)), 7.61 (dd, 1H,
3 J = 7.8 Hz,
4 J = 1.6 Hz, (CH(5)), 7.49 (dd, 2H,
3 J = 7.9 Hz,
4 J = 1.9 Hz, CH(10 + 14)), 7.45 - 7.29 (m, 3H, CH(11 +
12 + 13)), 7.24 (ddd, 1H,
3 J = 8.1 Hz,
3 J = 7.2 Hz,
3 J = 1.6 Hz, CH(7)), 7.11 (s, 1H, NH(1)), 6.78 - 6.72 (m, 1H, CH(8)), 6.71 - 6.63 (m, 1H, CH(6)), 5.75 (t, 1H,
3 J = 1.9 Hz, CH(2));
13 C-NMR (63 MHz, DMSO-d6): δ = 163.6 (C=O(4)), 147.8 (Cquart(8a)), 141.6 (Cquart(9)), 133.3 (CH(7)), 128.4 (CH(12)), 128.3 (CH(11 + 13)), 127.3 (CH(5)), 126.8 (CH(10 + 14)), 117.1 (CH(6)), 114.9 (Cquart(4a)), 114.4 (CH(8)), 66.5 (CH(2)) ppm;
MS: (EI,
70 eV) m/z (%) =
224 ([M] + , 19),
223 (27),
147 (100),
120 (42),
119 (15),
104 (10),
92 (29),
77 (20),
65 (14),
64 (10),
51 (15). 2-Phenyl-7-chloro-2,3-dihydroquinazolin-4(1H)-one
1 H-NMR (300 MHz, DMSO-d6): δ = 8.47 (s, 1H, NH(3)), 7.54 (d, 1H,
4 J = 2.6 Hz, CH(8)), 7.50 C 7.45 (m, 2H, CH(10 +14)), 7.44 C 7.34 (m, 3H, CH(11 +
12 + 13)), 7.34 C 7.32 (m, 1H, NH(1)), 7.28 (dd, 1H,
3 J = 8.7 Hz,
4 J = 2.7 Hz, CH(6))), 6.78 (d, 1H,
3 J = 8.7 Hz, CH(8)), 5.78 (dd, 1H,
3 J = 1.9 Hz,
3 J = 1.9 Hz, CH(2)) ppm;
13 C-NMR (75 MHz, DMSO-d6): δ = 162.4 (C=O(4)), 146.6 (Cquart(8a)), 141.2 (Cquart(9)), 133.1 (Cquart(7)), 128.6 CH(12)), 128.4 (CH(11 + 13)), 126.8 (CH(10 + 14)), 126.4 (CH(5)), 120.7 (CH(6)), 116.4 CH(8)), 116.0 (Cquart(4a)), 66.4 (CH(2)) ppm;
MS: (EI,
70 eV) m/z (%) =
259 ([M] + , 10),
258 (20),
257 (27),
183 (37),
182 (14),
181 (100),
156 (18),
155 (11),
154 (46),
153 (15),
126 (26),
104 (17),
90 (10),
77 (27),
63 (18),
51 (19). 2-Phenyl-6-chloro-2,3-dihydroquinazolin-4(1H)-one
1 H-NMR (300 MHz, DMSO-d6): δ = 8.49 (s, 1H, NH(3)), 7.54 (d, 1H,
4 J = 2.6 Hz, CH(5)), 7.50 C 7.45 (m, 2H, CH(10 + 14)), 7.44 C 7.35 (m, 3H, (CH(11 +
12 + 13)), 7.34 (s, 1H, NH(1)), 7.28 (dd, 1H,
3 J = 8.7 Hz,
4 J = 2.6 Hz, CH(7)), 6.78 (d, 1H,
3 J = 8.7 Hz, CH(8)), 5.78 (dd, 1H,
3 J = 1.8 Hz,
3 J = 1.8 Hz, CH(2)) ppm;
13 C-NMR (75 MHz, DMSO-d6): δ = 162.4 (C=O), 146.6 (Cquart(8a)), 141.2 (Cquart(9)), 133.1 (Cquart(6)), 128.6 (CH(12)), 128.4 (CH(11 + 13)), 126.8 (CH (10 + 14)), 126.4 CH(5)), 120.7 (CH(7)), 116.4 (CH(8)), 116.0 (Cquart(4a)), 66.4 (CH(2)) ppm;
MS: (EI,
70 eV) m/z (%) =
259 ([M] + , 10),
258 (23),
257 (27),
183 (30),
182 (11),
181 (100),
156 (12),
155 (10),
154 (34),
153 (18),
126 (22),
125 (10),
104 (12),
99 (10),
90 (11),
77 (24),
75 (10),
63 (16),
51 (15). 2-Phenyl-5-fluoro-2,3-dihydroquinazolin-4(1H)-one
1 H-NMR (300 MHz, DMSO-d6): δ = 8.33 (s, 1H, NH(3)), 7.51 C 7.45 (m, 3H, CH(10 + 14) + NH(1)), 7.44 C 7.34 (m, 3H, CH(11 +