编辑: 252276522 2019-07-13
Supporting Information General remarks: All Chemicals were commercial available and were used without further purification.

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 +

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