Molecules 2013, 18
1979
127.80, 129.69, 130.54, 130.85, 131.37, 132.36, 132.52, 132.56, 132.75, 134.14, 134.75, 134.91,
142.65, 144.43, 177.13, 178.22. ESI HRMS m/z 505.9741 ([M+Na]+ calcd 505.9730).
2-Bis-(2-chlorobenzoyl)amino-3-bromo-1,4-naphthoquinone (3e). Yellow crystal (34%). Mp: 232–234 °C.
IR (cm−1) 1728, 1688, 1671, 1588, 1468. 1H-NMR (CDCl3) 7.12–7.14 (d, 2H, J = 7.88 Hz), 7.19–7.23
(dd, 2H, J = 1.64, 7.56 Hz), 7.27–7.31 (dt, 2H, J = 1.28, 7.60 Hz), 7.80–7.85 (m, 2H), 7.93–7.94 (d,
2H, 5.2 Hz), 8.16–8.20 (m, 1H), 8.23–8.27 (m, 1H). 13C-NMR (CDCl3) 126.65, 127.66, 128.08,
129.63, 130.49, 130.81, 131.23, 132.25, 134.68, 134.80, 140.78, 145.81, 167.57, 177.26, 177.81. ESI
HRMS m/z 549.9240 ([M+Na]+ calcd 549.9224).
2-Bis-(2-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone (3f). Yellow solid. (64%) Mp: 195–200 °C.
1
IR (cm−1) 3090, 2959, 1718, 1673, 1658, 1620, 1590, 1263, 1218, 1234, H-NMR (CDCl3) 4.30
(s, 3H), 7.19–7.28 (m, 6H), 7.73–7.80 (m, 4H), 8.07–8.12 (m, 2H). 13C-NMR (CDCl3) 180.88, 179.74,
168.21, 155.31, 134.30, 133.61, 132.08, 131.67, 131.10, 130.57, 130.16, 129.32, 128.67, 126.46,
126.27, 115.41, 103.74, 102.58, 61.47. ESI HRMS m/z 502.0224 ([M+Na]+ calcd 502.0225).
2-Bis-(3-chlorobenzoyl)amino-3-chloro-1,4-naphthoquinone (3g). Yellow solid. (31%). Mp: 258–260 °C.
1
IR (cm−1) 3075, 1713, 1698, 1672, 1591, 1571. H-NMR (CDCl3) 7.27–7.31 (t, 2H, J = 7.85 Hz),
7.42–7.45 (ddd, 2H, J = 1.03, 2.09, 8.07 Hz), 7.60–7.63 (td, 2H, J = 1.07, 7.68 Hz), 7.70–7.71 (t, 2H,
13
J = 1.82), 7.80–7.85 (m, 2H), 8.11–8.14 (m, 1H), 8.21–8.23 (m, 1H). C-NMR (CDCl3) 127.02,
127.93, 128.03, 129.34, 130.21, 130.75, 131.55, 133.29, 135.14, 135.21, 136.06, 143.00, 143.84,
170.20, 177.25, 178.66. ESI HRMS m/z 505.9741 ([M+Na]+ calcd 505.9730).
2-Bis-(3-chlorobenzoyl)amino-3-bromo-1,4-naphthoquinone (3h). Yellow solid (26%) Mp: 204–206 °C.
IR (cm−1) 3074, 1698, 1671, 1589, 1566. 1H-NMR (CDCl3) 7.27–7.30 (t, 2H, J = 7.92 Hz), 7.41–7.44
(ddd, 2H, J = 1.04, 2.08, 8.04 Hz), 7.62–7.65 (td, 2H, J = 1.12, 7.72 Hz), 7.72–7.73 (t, 2H, J = 1.84 Hz),
13
7.78–7.85 (m, 2H), 8.10–8.14 (m, 1H), 8.20–8.24 (m, 1H). C-NMR (CDCl3) 127, 128.09, 128.40,
129.49, 130.25, 130.78, 131.49, 133.32, 135.15, 135.18, 135.24, 136.25, 139.56, 147.05, 170.21,
177.50, 178.43. ESI HRMS m/z 549.9236 ([M+Na]+ calcd 549.9224).
2-Bis-(3-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone (3i). Yellow solid. (37%) Mp: 182–184 °C.
1
IR (cm−1) 3107, 2960, 1707, 1689, 1670, 1657, 1604, 1572, 1283, 1266, 1239, 1218. H-NMR
(CDCl3) 4.19 (s, 3H), 7.26–7.30 (t, 2H, J = 7.984 Hz), 7.40–7.43 (ddd, 2H, J = 1.04, 2.08, 8.04 Hz),
7.58–7.61 (td, 2H, J = 1.16, 7.72 Hz), 7.68–7.69 (t, 2H, J = 1.84 Hz), 7.73–7.77 (m, 2H), 8.05–8.09
13
(m, 2H). C-NMR (CDCl3) 180.66, 179.85, 170.63, 154.37, 135.97, 134.53, 134.35, 133.83, 132.37,
131.06, 130.29, 130.21, 129.58, 128.60, 126.58, 126.51, 126.32, 61.53. ESI HRMS m/z 502.0219
([M+Na]+ calcd 502.0225).
2-Bis-(4-chlorobenzoyl)amino-3-chloro-1,4-naphthoquinone (3j). Yellow solid. (27%). Mp: 212–213 °C.
IR (cm−1) 1737, 1714, 1696, 1673, 1589, 1571. 1H-NMR (CDCl3) 7.33–7.36 (td, 4H, J = 2.34, 8.54 Hz),
7.68–7.72 (td, 4H, J = 2.40, 8.47 Hz), 7.79–7.85 (m, 2H), 8 09–8.11 (dd, 1H, J = 2.50, 6.56 Hz),
13
8.20–8.22 (dd, 1H, J = 2.40, 6.66 Hz). C-NMR (CDCl3) 127.72, 127.80, 129.18, 130.34, 130.50,