Organic & Biomolecular Chemistry
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CH(5)), 7.51 (1H, s, NH(1)), 7.31 (2H, d, J = 8.1 Hz, CH(10 + (1)), 6.75 (1H, dd, 3J = 8.2 Hz, 4J = 1.1 Hz, CH(8)), 6.62 (1H, ddd,
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14)), 7.25 (1H, ddd, J = 8.4 Hz, J = 7.2 Hz, J = 1.6 Hz, CH(7)), 3J = 8.1 Hz, J = 7.1 Hz, J = 1.2 Hz, CH(6)), 4.41–4.37 (1H, m,
7.17 (2H, d, 3J = 8.0 Hz, CH(11 + 13)), 6.74 (1H, dd, 3J = 8.2 Hz, CH(2)), 2.03–1.90 (1H, m, CH(9)), 0.93 (3H, d, 3J = 6.9 Hz, CH3),
4J = 0.7 Hz, CH(8)), 6.65 (1H, ddd, J = 8.1 Hz, J = 7.2 Hz, J = 0.89 (3H, d, J = 6.8 Hz, CH3) ppm; 13C-NMR (63 MHz, DMSO-
1.1 Hz, CH(6)), 5.74–5.67 (1H, m, CH(2)), 2.27 (3H, s, CH3(15)) d6): δ = 189.3 (CvS(4)), 4.2 (Cquart(8a)), 133.9 (CH(7)), 131.5
ppm; 13C-NMR (126 MHz, DMSO-d6): δ = 189.1 (CvS(4)), 143.4 (CH(5)), 119.5 (Cquart(4a)), 116.8 (CH(6)), 114.5 (CH(8)), 69.2
(Cquart(8a)), 138.0 (Cquart(9)), 137.7 (Cquart(12)), 134.0 (CH(7)), (CH(2)), 32.17 (CH(9)), 17.08 (CH3(Me)), 16.66 (CH3(Me)) ppm;
131.4 (CH(5)), 128.9 (CH(11 + 13)), 126.4 (CH(10 + 14)), 119.5 GC/MS: (EI, 70 eV) m/z (%) = 206 ([M]+, 6), 164 (10), 163 (100),
(Cquart(4a)), 117.3 (CH(6)), 114.8 (CH(8)), 65.4 (CH(2)), 20.7 136 (6), 129 (12), 108 (5), 41 (6); IR: (ATR) ˜ν = 3279 (m), 3139
(CH3(15)) ppm; GC/MS: (EI, 70 eV) m/z (%) = 254 ([M]+, 63), (m), 3057 (w), 2997 (w), 2955 (m), 2909 (w), 2865 (w), 1612 (m),
253 (19), 221 (100), 219 (38), 206 (17), 163 (28), 136 (30), 129 1535 (m), 1474 (m), 1279 (m), 1216 (s), 1146 (s), 981 (m), 766
(24), 102 (17), 77 (17), 44 (17), 32 (22); IR: (ATR) ˜ν = 3270 (m), (s), 749 (s), 689 (m), 435 (s) cm−1; HRMS (ESI-TOF) m/z: Calcd
3144 (m), 3029 (w), 2974 (w), 2911 (w), 2842 (w), 16.12 (m), for C11H14N2S1, 206.08722, found mass: 206.08683.
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1529 (s), 1209 (s), 1198 (s), 1147 (s), 1007 (m), 817 (s), 586 (s);
2-(Cyclohexyl)-2,3-dihydroquinazoline-4(1H)-thione
(2j).
493 (s) cm−1; HRMS (ESI-TOF) m/z: Calcd for C15H14N2S1, MP.: 182–183 °C; 1H-NMR (300 MHz, DMSO-d6): δ = 10.11 (1H,
254.08722, found mass: 254.08698.
s, NH(3)), 8.02 (1H, dd, 3J = 8.0 Hz, 4J = 1.3 Hz, CH(5)), 7.23
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(E)-2-(1-Phenylprop-1-en-2-yl)-2,3-dihydroquinazoline-4(1H)-
(1H, ddd, J = 8.4 Hz, J = 7.1 Hz, J = 1.5 Hz, CH(7)), 6.97 (1H,
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thione (2g). MP.: 198–199 °C; H-NMR (300 MHz, DMSO-d6): δ s, NH(1)), 6.74 (1H, dd, 3J = 8.2 Hz, 3J = 0.8 Hz, CH(8)), 6.61
= 10.27 (1H, s, NH(3)), 8.07 (1H, d, 3J = 6.9 Hz, CH(5)), (1H, ddd, J = 8.1 Hz, J = 5.8 Hz, J = 1.1 Hz, CH(6)), 4.36 (1H,
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7.42–7.21 (7H, m, NH(1), CH(7 + 12 + 13 + 14 + 15 + 16)), 6.75 s, CH(2)), 1.79–0.99 (11H, m, CH2(Cy)) ppm; 13C-NMR
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(1H, d, J = 8.1 Hz, CH(8)), 6.69–6.62 (1H, m, CH(6)), 6.59 (1H, (63 MHz, DMSO-d6): δ = 189.0 (CvS(4)), 144.0 (Cquart(8a)),
s, CH(10)), 5.27 (1H, s, CH(2)), 1.91 (3H, s, CH3(17)) ppm; 133.9 (CH(7)), 131.5 (CH(5)), 119.5 (Cquart(4a)), 116.7 (CH(6)),
13C-NMR (63 MHz, DMSO-d6): δ = 189.7 (CvS(4)), 144.1 114.5 (CH(8)), 68.38 (CH(2)), 42.0 (CH2(Cy)), 27.0 (CH2(Cy)),
(Cquart(8a)), 136.3 (Cquart(11)), 135.6 (Cquart(9)), 134.0 (CH(7)), 26.8 (CH2(Cy)), 25.8 CH2(Cy)), 25.4 (CH2(Cy)), 25.3 (CH(Cy))
131.5 (CH(5)), 128.9 (CH(13 + 15)), 128.5 (CH(14)), 128.3 ppm; MS: (EI, 70 eV) m/z (%) = 246 ([M]+, 16), 189 (10), 164
(CH(12 + 16)), 127.1 (CH(10)), 119.0 (Cquart(4a)), 117.1 (CH(6)), (19), 163 (100), 129 (10); IR: (ATR) ˜ν = 3338 (w), 3150 (w), 3041
114.5 (CH(8)), 70.8 (CH(2)), 13.5 (CH3(17)) ppm; MS: (EI, 70 (w), 2992 (w), 2927 (m), 2848 (w), 1610 (m), 1576 27 (m), 1536
eV) m/z (%) = 280 ([M]+, 55), 279 (53), 278 (23), 277 (33), 263 (s), 1213 (s), 1148 (m), 1162 (m), 1003 (m), 989 (m), 956 (m),
(23), 247 (100), 246 (33), 245 (86), 232 (26), 231 (28), 163 (92), 761 (s), 743 (s), 530 (s), 524 (s) cm−1; HRMS (ESI-TOF) m/z:
129 (23), 115 (23); IR: (ATR) ˜ν = 3317 (w), 3130 (w), 2977 (w), Calcd for C14H18N2S1, 246.11852, found mass: 246.11846.
1608 (m), 1573 (m), 1518 (m), 1208 (s), 1155 (m), 1126 (m), 993
2-(Benzo[b]thiophen-2-yl)-2,3-dihydroquinazoline-4(1H)-
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(m), 756 (s), 699 (s), 516 (s), 443 (s), 427 (m) cm−1; HRMS thione (2k). M.P.: 253–255 °C; H-NMR (300 MHz, DMSO-d6):
(ESI-TOF; M + H)+ m/z: Calcd for C17H16N2S1, 281.11070, found δ = 10.57 (1H, br s, (NH(3)), 8.20–8.14 (1H, m, CH(12)), 8.11
mass: 281.11077.
(1H, dd, 3J = 8.0 Hz, 4J = 1.4 Hz, CH(15)), 8.04–7.99 (1H, m,
2-(4-Hydroxyphenyl)-2,3-dihydroquinazoline-4(1H)-thione CH(5)), 7.66 (1H, s, CH(10)), 7.55 (1H, s, NH(1)), 7.49–7.37 (2H,
(2h). M.P.: 214–216 °C; 1H-NMR (300 MHz, DMSO-d6): δ = m, CH(13 + 14)), 7.29 (1H, m, CH(7)), 6.80–6.66 (1H, m, (CH(6 +
10.36 (1H, d, 3J = 2.9 Hz, NH(3)), 9.52 (1H, s, OH), 8.05 (1H, dd, 8)), 6.18 (1H, m, CH(2)) ppm; 13C-NMR (75 MHz, DMSO-d6): δ =
3J = 8.0 Hz, 4J = 1.6 Hz, CH(5)), 7.41–7.36 (1H, m, NH(2)), 189.7 (CvS(4)), 143.7 (Cquart(8a)), 140.3 (Cquart(9), 136.6
7.30–7.20 (3H, m, CH(7 + 10 + 14), 6.75–6.69 (3H, m, CH(8 + 11 (Cquart(11a)), 134.5 (Cquart(15a)), 134.1 (CH(7)), 131.6 (CH(5)),
+ 13), 6.65 (1H, ddd, 3J = 8.1 Hz, 3J = 7.1 Hz, 4J = 1.1 Hz, CH(6)), 126.9 (CH(13)), 124.7 (CH(14)), 124.2 (CH(15)), 123.1 (CH(10)),
5.63 (1H, dd, 3J = 3.3 Hz, 3J = 1.7 Hz, CH(2)) ppm; 13C-NMR 123.1 (CH(12)), 119.7 (Cquart(4a)), 117.6 (CH(6)), 114.9 (CH(8)),
(75 MHz, DMSO-d6): δ = 189.1 (CvS(4)), 157.7 (Cquart(10)), 62.0 (CH(2)) ppm; GC/MS: (EI, 70 eV) m/z (%) = 297 (10), 296
143.7 (Cquart(8)), 134.0 (CH(7)), 131.5 (CH(5)), 131.0 (Cquart(9)), ([M]+, 54), 264 (21), 263 (100), 262 (36), 261 (28), 178 (10), 129
128.0 (CH(11 + 13)), 119.4 (Cquart(4a)), 117.2 (CH(6)), 115.0 (CH (11), 44 (11); IR: (ATR) ˜ν = 3274 (w), 3105 (w), 2960 (w), 1607
(10 + 14)), 114.7 (CH(8)), 65.8 (CH(2)) ppm; MS: (EI, 70 eV) m/z (w), 1579 (m), 1521 (m), 1460 (m), 1425 (m), 1343 (m), 1240
(%) = 256 ([M]+, 37), 255 (10), 254 (16), 224 (15), 223 (81), 222 (m), 1208 (s), 1146 (m), 1125 (m), 1002 (S), 936 (m), 848 (m),
(100), 221 (50), 195 (17), 129 (10), 119 (13); IR: (ATR) ˜ν = 3149 754 (s), 733 (S), 600 (s), 522 (s), 453 (S), 424 (s) cm−1; HRMS
(br, m), 1608 (m), 1575 (w), 1530 (m), 1511 (s), 1480 (m), 1365 (ESI-TOF) m/z: Calcd for C16H12N2S2, 296.04364, found mass:
(m), 1297 (w), 1242 (m), 1196 (s), 1168 (s), 1154 (s), 1125 (s), 296.04315.
1015 (m), 999 (s), 829 (s), 760 (s). 750 (s), 706 (s), 526 (s),
501 (s), 466 (s) cm−1 HRMS (ESI-TOF) m/z: Calcd for 138–139 °C; 1H-NMR (300 MHz, DMSO-d6): δ = 10.12 (1H, d,
C14H12O1N2S1, 256.06649, found mass: 256.06662.
3J = 2.5 Hz, NH(3)), 8.03 (1H, dd, 3J = 8.0 Hz, 4J = 1.6 Hz,
2-(Isopropyl)-2,3-dihydroquinazoline-4(1H)-thione (2i). MP.: CH(5)), 7.25 (1H, ddd, J = 8.5 Hz, J = 7.1 Hz, J = 1.6 Hz, CH
2-Pentyl-2,3-dihydroquinazoline-4(1H)-thione
(2l). M.P.:
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185–186 °C; 1H-NMR (300 MHz, DMSO-d6): δ = 10.09 (1H, s, (7)), 6.90 (1H, s, NH(1)), 6.73 (1H, dd, J = 8.3 Hz, J = 1.1 Hz,
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NH(3)), 8.03 (1H, dd, J = 8.0 Hz, J = 1.6 Hz, CH(5)), 7.24 (1H, CH(8)), 6.66 (1H, ddd, 3J = 8.1 Hz, 3J = 7.1 Hz, 4J = 1.1 Hz,
ddd, 3J = 8.4 Hz, 3J = 7.1 Hz, 4J = 1.6 Hz, CH(7)), 6.92 (1H, s, NH CH(6)), 4.62 (1H, tdd, 3J = 5.4 Hz, 3J = 2.5 Hz, 3J = 1.2 Hz,
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