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Organic & Biomolecular Chemistry
192–194 °C. White solid. 1H NMR (400 MHz, chloroform-d) 126.0, 124.3, 121.7, 121.6, 119.1, 118.7, 114.6, 57.9. HRMS
δ 9.32 (s, 1H), 8.39 (dd, J = 1.6, 0.7 Hz, 1H), 8.00–7.93 (m, 2H), (ESI+) m/z calcd for C23H15BrN2NaOS+ [M + Na]+: 468.9981,
7.46 (ddd, J = 8.3, 7.1, 1.2 Hz, 1H), 7.39–7.34 (m, 2H), found: 468.9980.
7.34–7.25 (m, 4H), 7.17 (dd, J = 7.9, 1.5 Hz, 2H), 5.53 (s, 2H),
3-(Benzo[d]thiazol-2-yl)-1-benzyl-6-phenylquinolin-4(1H)-one
2.44 (s, 3H). 13C NMR (100 MHz, chloroform-d) δ 174.4, 162.2, (4f). Compound 4f was prepared (32.4 mg, 73% yield) accord-
150.9, 143.9, 136.8, 135.6, 135.4, 134.5, 134.0, 129.2, 128.4, ing to GP from quinolone derivative (0.1 mmol). mp
127.1, 126.7, 126.0, 126.0, 124.1, 121.7, 121.3, 116.8, 113.7, 283–284 °C. White solid. 1H NMR (400 MHz, chloroform-d)
57.7, 21.0. HRMS (ESI+) m/z calcd for C24H18N2NaOS+ δ 9.19 (s, 1H), 8.83 (d, J = 2.2 Hz, 1H), 8.01–7.96 (m, 1H),
[M + Na]+: 405.1032, found: 405.1042.
7.95–7.90 (m, 1H), 7.76 (dd, J = 8.8, 2.3 Hz, 1H), 7.67–7.61 (m,
3-(Benzo[d]thiazol-2-yl)-1-benzyl-6-methoxyquinolin-4(1H)-one 2H), 7.49–7.39 (m, 4H), 7.38–7.26 (m, 5H), 7.22–7.15 (m, 2H),
(4b). Compound 4b was prepared (30.3 mg, 76% yield) accord- 5.53 (s, 2H). 13C NMR (100 MHz, chloroform-d) δ 174.6, 162.2,
ing to GP from quinolone derivative (0.1 mmol). mp 144.3, 139.1, 138.1, 138.0, 135.4, 134.4, 131.5, 129.4, 129.0,
224–226 °C. White solid. 1H NMR (400 MHz, chloroform-d) 128.6, 128.0, 127.5, 127.1, 126.2, 126.1, 125.2, 124.4, 121.8,
δ 9.25 (s, 1H), 8.00 (d, J = 3.0 Hz, 1H), 7.99–7.93 (m, 2H), 7.46 121.2, 117.6, 57.9. HRMS (ESI+) m/z calcd for C29H20N2NaOS+
(ddd, J = 8.2, 7.1, 1.3 Hz, 1H), 7.38–7.25 (m, 5H), 7.19–7.12 (m, [M + Na]+: 467.1189, found: 467.1206.
3H), 5.53 (s, 2H), 3.91 (s, 3H). 13C NMR (100 MHz, chloroform-
3-(Benzo[d]thiazol-2-yl)-1-benzyl-8-methoxyquinolin-4(1H)-one
d) δ 174.0, 162.2, 157.2, 151.5, 143.0, 135.8, 134.5, 133.3, (4g). Compound 4g was prepared (28.7 mg, 72% yield) accord-
129.3, 128.6, 128.5, 125.9, 125.9, 124.0, 123.1, 121.7, 121.5, ing to GP from quinolone derivative (0.1 mmol). mp
1
118.5, 113.4, 106.5, 57.9, 55.8. HRMS (ESI+) m/z calcd for 256–258 °C. White solid. H NMR (400 MHz, chloroform-d) δ
C24H18N2NaO2S+ [M + Na]+: 421.0981, found: 421.0980.
9.12 (s, 1H), 8.28 (dd, J = 8.1, 1.4 Hz, 1H), 8.00–7.92 (m, 2H),
3-(Benzo[d]thiazol-2-yl)-1-benzyl-6-fluoroquinolin-4(1H)-one 7.45 (ddd, J = 8.2, 7.2, 1.3 Hz, 1H), 7.38 (t, J = 8.0 Hz, 1H), 7.34
(4c). Compound 4c was prepared (30.1 mg, 78% yield) accord- (ddd, J = 8.1, 7.2, 1.2 Hz, 1H), 7.31–7.25 (m, 2H), 7.23–7.19
ing to GP from quinolone derivative (0.1 mmol). mp (m, 1H), 7.07 (ddd, J = 9.2, 8.0, 1.3 Hz, 3H), 5.90 (s, 2H), 3.69
244–246 °C. White solid. 1H NMR (400 MHz, chloroform-d) (s, 3H). 13C NMR (100 MHz, chloroform-d) δ 173.9, 161.9,
δ 9.25 (s, 1H), 8.22 (dd, J = 8.7, 3.0 Hz, 1H), 7.99–7.95 (m, 1H), 150.1, 146.7, 137.3, 135.8, 130.3, 129.8, 128.7, 127.6, 125.8,
7.95–7.91 (m, 1H), 7.46 (ddd, J = 8.3, 7.2, 1.3 Hz, 1H), 125.5, 125.5, 124.0, 121.6, 121.4, 119.7, 114.8, 113.9, 62.1, 56.2.
7.40–7.30 (m, 5H), 7.29–7.24 (m, 1H), 7.16 (dd, J = 8.0, 1.5 Hz, HRMS (ESI+) m/z calcd for C24H18N2NaO2S+ [M + Na]+:
2H), 5.53 (s, 2H). 13C NMR (100 MHz, chloroform-d) δ 173.7, 421.0981, found: 421.0991.
161.6, 161.1, 158.6, 151.1, 144.1, 135.6, 135.3, 134.1, 129.4,
3-(Benzo[d]thiazol-2-yl)-1-benzyl-8-fluoroquinolin-4(1H)-one
129.0, 128.9, 128.7, 126.1, 125.9, 124.3, 121.7, 121.6, 121.2, (4h). Compound 4h was prepared (25.1 mg, 65% yield) accord-
121.0, 119.3, 119.2, 113.7, 112.3, 112.1, 58.1. HRMS (ESI+) m/z ing to GP from quinolone derivative (0.1 mmol). mp
1
calcd for C23H15FN2NaOS+ [M
409.0774.
+
Na]+: 409.0781, found: 245–247 °C. White solid. H NMR (400 MHz, DMSO-d6) δ 9.36
(s, 1H), 8.29 (dd, J = 8.0, 1.6 Hz, 1H), 8.10 (dd, J = 7.9, 1.1 Hz,
3-(Benzo[d]thiazol-2-yl)-1-benzyl-6-chloroquinolin-4(1H)-one 1H), 7.96 (dd, J = 8.2, 1.0 Hz, 1H), 7.60 (ddd, J = 14.8, 7.9,
(4d). Compound 4d was prepared (33.4 mg, 83% yield) accord- 1.7 Hz, 1H), 7.56–7.45 (m, 2H), 7.43–7.36 (m, 1H), 7.40–7.30
ing to GP from quinolone derivative (0.1 mmol). mp (m, 2H), 7.28 (t, J = 7.3 Hz, 1H), 7.20 (dd, J = 7.5, 1.5 Hz, 2H),
268–270 °C. White solid. 1H NMR (400 MHz, chloroform-d) 5.91 (d, J = 2.9 Hz, 2H). 13C NMR (100 MHz, DMSO-d6) δ 172.8,
δ 9.12 (s, 1H), 8.47 (d, J = 2.5 Hz, 1H), 7.95 (dd, J = 7.8, 1.0 Hz, 172.8, 161.3, 153.4, 151.8, 150.9, 147.3, 137.5, 135.7, 129.8,
1H), 7.87 (dd, J = 8.1, 1.0 Hz, 1H), 7.44 (ddd, J = 8.3, 7.1, 129.2, 128.9, 128.8, 128.1, 126.5, 126.3, 126.2, 126.1, 124.6,
1.2 Hz, 1H), 7.39 (dd, J = 9.1, 2.5 Hz, 1H), 7.35 (dd, J = 8.1, 1.1 123.1, 123.0, 122.2, 122.0, 120.4, 120.2, 113.9, 60.5, 60.4.
Hz, 1H), 7.30 (ddd, J = 7.8, 7.0, 0.9 Hz, 3H), 7.24 (dd, J = 5.0, HRMS (ESI+) m/z calcd for C23H15FN2NaOS+ [M + Na]+:
4.1 Hz, 1H), 7.16–7.07 (m, 2H), 5.47 (s, 2H). 13C NMR (100 MHz, 409.0781, found: 409.0776.
chloroform-d) δ 173.3, 161.2, 151.4, 144.1, 137.1, 135.7, 134.0,
3-(Benzo[d]thiazol-2-yl)-1-methylquinolin-4(1H)-one
(4i).
132.7, 131.4, 129.4, 128.6, 128.2, 126.7, 126.0, 125.9, 124.2, Compound 4i was prepared (21.6 mg, 74% yield) according to
121.7, 121.6, 118.5, 114.6, 57.9. HRMS (ESI+) m/z calcd for GP from quinolone derivative (0.1 mmol). mp 302–304 °C.
C23H15ClN2NaOS+ [M + Na]+: 425.0486, found: 425.0479.
White solid. 1H NMR (400 MHz, DMSO-d6) δ 9.25 (s, 1H),
3-(Benzo[d]thiazol-2-yl)-1-benzyl-6-bromoquinolin-4(1H)-one 8.45–8.40 (m, 1H), 8.06 (ddd, J = 7.9, 1.3, 0.7 Hz, 1H), 7.95
(4e). Compound 4e was prepared (22.8 mg, 51% yield) accord- (ddd, J = 8.1, 1.1, 0.6 Hz, 1H), 7.87–7.83 (m, 2H), 7.57 (ddd, J =
ing to GP from quinolone derivative (0.1 mmol). mp 8.0, 4.6, 3.4 Hz, 1H), 7.48 (ddd, J = 8.2, 7.2, 1.3 Hz, 1H), 7.36
254–256 °C. White solid. 1H NMR (400 MHz, chloroform-d) (ddd, J = 8.1, 7.2, 1.1 Hz, 1H), 4.10 (s, 3H). 13C NMR (100 MHz,
δ 9.22 (s, 1H), 8.71 (d, J = 2.3 Hz, 1H), 7.97 (ddd, J = 7.9, 1.3, DMSO-d6) δ 173.7, 162.1, 151.9, 145.5, 140.1, 135.6, 133.1,
0.6 Hz, 1H), 7.95–7.89 (m, 1H), 7.60 (dd, J = 9.0, 2.4 Hz, 1H), 126.9, 126.5, 126.3, 125.4, 124.3, 122.1, 121.8, 117.9, 113.2,
7.46 (ddd, J = 8.2, 7.1, 1.3 Hz, 1H), 7.39–7.28 (m, 4H), 41.6. HRMS (ESI+) m/z calcd for C17H12N2NaOS+ [M + Na]+:
7.27–7.22 (m, 1H), 7.15 (dd, J = 7.9, 1.5 Hz, 2H), 5.51 (s, 2H). 315.0563, found: 315.0548.
13C NMR (100 MHz, chloroform-d) δ 173.2, 161.3, 151.1, 144.3,
137.6, 135.6, 135.5, 134.0, 130.0, 129.4, 128.7, 128.5, 126.1, pound 4j was prepared (16.6 mg, 52% yield) according to GP
3-(Benzo[d]thiazol-2-yl)-1-benzylpyridin-4(1H)-one (4j). Com-
5724 | Org. Biomol. Chem., 2014, 12, 5719–5726
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