January 2014
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129.49, 130.87, 130.90, 131.05, 131.14, 133.09, 134.22, 134.66, Yield 83%. mp 274–275°C. 1H-NMR (DMSO-d6) δ: 4.85
135.03, 162.81, 164.23, 166.74, 181.33, 182.39, 192.42 (C=O). (s, 2H, OCH2), 6.92 (dd, J=8.8, 2.0Hz, 1H-C(3)), 7.07 (d,
Anal. Calcd for C22H13FO4: C 73.33, H 3.64. Found: C 73.25, J=2.0Hz, 1H-C(1)), 7.10–7.13 (m, 1H, Ar-H), 7.27–7.31
H 3.69.
(m, 1H, Ar-H), 7.41–7.50 (m, 3H, Ar-H), 7.70–7.73 (m, 1H,
2-(2-(4-Methoxyphenyl)-2-oxoethoxy)anthracene-9,10-dione Ar-H), 7.82–7.86 (m, 2H, Ar-H), 7.89 (d, J=8.8Hz, 1H-C(4)),
1
(10c): Yield 89%. mp 186–187°C. H-NMR (DMSO-d6) δ: 7.80–8.03 (m, 2H, Ar-H), 8.33–8.36 (m, 1H, Ar-H), 10.36 (s,
3.89 (s, 3H, MeO), 5.85 (s, 2H, OCH2), 7.12–7.15 (m, 2H, 1H, CONH), 11.18 (s, 1H, NH). 13C-NMR (DMSO-d6) δ: 67.79
Ar-H), 7.50 (dd, J=8.8, 2.8Hz, 1H-C(3)), 7.60 (d, J=2.8Hz, (CH2O), 95.75, 108.15, 110.63, 115.98, 116.83, 118.59, 119.37,
1H-C(1)), 7.88–7.95 (m, 2H, Ar-H), 8.03–8.06 (m, 2H, Ar-H), 120.33, 120.93, 122.51, 124.33, 124.80, 126.47, 127.33, 127.46,
8.15–8.22 (m, 2H, Ar-H), 8.18 (d, J=8.8Hz, 1H-C(4)). 128.36, 129.96, 133.31, 136.01, 139.80, 140.85, 156.95, 167.09
13C-NMR (DMSO-d6) δ: 55.66 (MeO), 70.33 (CH2O), 111.09, (C=O). Anal. Calcd for C23H17N2O2·0.2 H2O: C 77.90, H 5.02,
114.14, 121.29, 126.65, 126.71, 126.98, 129.46, 130.33, 133.07, N 7.57. Found: C 77.76, H 5.02, N 7.54.
134.19, 134.63, 134.98, 162.94, 163.78, 181.30, 182.37, 191.99
(C=O). Anal. Calcd for C23H16O5: C 74.19, H 4.33. Found: C acetamide (16a): Yield 92%. mp 204–205°C. 1H-NMR
74.12, H 4.33. (DMSO-d6) δ: 4.98 (s, 2H, OCH2), 7.09–7.12 (m, 1H, Ar-H),
2-(9,10-Dioxo-9,10-dihydroanthracen-2-yloxy)-N-phenyl-
2-(2-(Biphenyl-4-yl)-2-oxoethoxy)anthracene-9,10-dione 7.33–7.37 (m, 2H, Ar-H), 7.54 (dd, J=8.8, 2.4Hz, 1H-C(3)),
(10d): Yield 92%. mp 195–196°C. 1H-NMR (DMSO-d6) 7.63–7.65 (m, 2H, Ar-H), 7.70 (d, J=2.4Hz, 1H-C(1)),
δ: 5.96 (s, 2H, OCH2), 7.45–7.48 (m, 1H, Ar-H), 7.52–7.54 7.89–7.95 (m, 2H, Ar-H), 8.18–8.22 (m, 2H, Ar-H), 8.21 (d,
(m, 2H, Ar-H), 7.55 (dd, J=8.8, 2.8Hz, 1H-C(3)), 7.65 (d, J=8.8Hz, 1H-C(4)), 10.27 (s, 1H, NH). 13C-NMR (DMSO-
J=2.8Hz, 1H-C(1)), 7.79–7.81 (m, 2H, Ar-H), 7.89–7.96 (m, d6) δ: 67.83 (CH2O), 111.86, 120.42, 121.96, 124.56, 127.38,
4H, Ar-H), 8.15–8.20 (m, 3H, Ar-H), 8.20 (d, J=8.8Hz, 127.45, 127.55, 129.50, 130.23, 133.73, 134.94, 135.37, 135.67,
1H-C(4)), 8.21–8.22 (m, 1H, Ar-H). 13C-NMR (DMSO-d6) δ: 138.90, 163.27, 166.40 (C=O), 182.05, 183.07. Anal. Calcd for
70.71 (CH2O), 111.21, 121.36, 126.73, 126.78, 127.11, 128.63, C22H15NO4: C 73.94, H 4.23, N 3.92. Found: C 73.91, H 4.25,
128.77, 129.20, 129.56, 132.91, 133.13, 134.28, 134.71, 135.07, N 3.92.
138.82, 145.43, 162.91, 181.39, 182.46, 193.37 (C=O). Anal.
Calcd for C28H18O4: C 80.37, H 4.34. Found: C 80.29, H 4.37.
2-(9,10-Dioxo-9,10-dihydroanthracen-2-yloxy)-N-(4-
fluorophenyl)acetamide (16b): Yield 98%. mp 215–216°C.
Production of 13–15, 16a–d, 17a–d, and 18a–d. General 1H-NMR (DMSO-d6) δ: 4.97 (s, 2H, OCH2), 7.16–7.21 (m, 2H,
Procedure A solution of 7/8/9/10a–d/11a–d/12a–d (1mmol) Ar-H), 7.54 (dd, J=8.8, 2.4Hz, 1H-C(3)), 7.64–7.68 (m, 2H,
in H2SO4 (3mL) was stirred at r.t. for 10min. To this solution, Ar-H), 7.70 (d, J=2.4Hz, 1H-C(1)), 7.91–7.94 (m, 2H, Ar-H),
was added sodium azide (2mmol) in one portion. The mixture 8.19–8.22 (m, 2H, Ar-H), 8.21 (d, J=8.8Hz, 1H-C(4)), 10.30
was stirred continuously at r.t. for 1h (TLC monitoring) and (s, 1H, NH). 13C-NMR (DMSO-d6) δ: 67.05 (CH2O), 111.18,
then poured into ice-water (100mL). The white solid thus 115.18, 115.41, 121.13, 121.49, 121.57, 126.60, 126.66, 126.81,
obtained was collected and purified by flash column chroma- 129.46, 132.97, 134.15, 134.51, 134.53, 134.59, 134.90, 157.04,
tography on silica gel using CH2Cl2/MeOH 10:1. The proper 159.43, 162.44, 165.58 (C=O), 181.26, 182.29. Anal. Calcd for
fractions were combined and evaporated to furnish a residual C22H14FNO4: C 70.40, H 3.76, N 3.73. Found: C 70.37, H 3.88,
solid which was crystallized from Et2O and CH2Cl2.
2-(9,10-Dioxo-9,10-dihydroanthracen-2-yloxy)-N-
N 3.76.
2-(9,10-Dioxo-9,10-dihydroanthracen-2-yloxy)-N-(4-
(naphthalen-2-yl)acetamide (13): Yield 86%. mp 229–230°C. methoxyphenyl)acetamide (16c): Yield 82%. mp 204–205°C.
1H-NMR (DMSO-d6) δ: 5.06 (s, 2H, OCH2), 7.41–7.50 (m, 2H, 1H-NMR (DMSO-d6) δ: 3.73 (s, 3H, MeO), 4.95 (s, 2H,
Ar-H), 7.57 (dd, J=8.8, 2.4Hz, 1H-C(3)), 7.67–7.69 (m, 1H, OCH2), 6.90–6.92 (m, 2H, Ar-H), 7.53 (dd, J=8.8, 2.8Hz,
Ar-H), 7.74 (d, J=2.4Hz, 1H-C(1)), 7.82–7.92 (m, 5H, Ar-H), 1H-C(3)), 7.54–7.56 (m, 2H, Ar-H), 7.70 (d, J=2.8Hz,
8.19–8.32 (m, 3H, Ar-H), 8.22 (d, J=8.8Hz, 1H-C(4)), 10.48 1H-C(1)), 7.91–7.94 (m, 2H, Ar-H), 8.18–8.21 (m, 2H, Ar-H),
(s, 1H, NH). 13C-NMR (DMSO-d6) δ: 67.18 (CH2O), 111.23, 8.20 (d, J=8.8Hz, 1H-C(4)), 10.30 (s, 1H, NH). 13C-NMR
115.94, 120.15, 121.24, 124.84, 126.49, 126.66, 126.72, 126.85, (DMSO-d6) δ: 55.86 (MeO), 67.88 (CH2O); 111.97, 114.58,
127.31, 127.44, 128.43, 129.52, 129.95, 133.03, 133.25, 134.21, 121.92, 122.06, 127.38, 127.45, 127.55, 130.22, 132.00, 133.76,
134.64, 134.97, 135.81, 162.58, 165.96 (C=O), 181.32, 181,35. 134.92, 135.35, 135.68, 156.30, 163.28, 165.90 (C=O), 182.03,
Anal. Calcd for C26H17NO4: C 76.65, H 4.21, N 3.44. Found: C 183.07. Anal. Calcd for C23H17NO5: C 71.31, H 4.42, N 3.62.
76.45, H 4.28, N 3.42.
Found: C 71.14, H 4.42, N 3.62.
N-(Naphthalen-2-yl)-2-(9-oxo-9H-xanthen-3-yloxy)-
N-(Diphenyl-4-yl)-2-(9,10-dioxo-9,10-dihydroanthracen-2-
1
1
acetamide (14): Yield 89%. mp 234–235°C. H-NMR (DMSO- yloxy)acetamide (16d). Yield 87%. mp 254–255°C. H-NMR
d6) δ: 5.02 (s, 2H, OCH2), 7.21 (dd, J=8.8, 2.4Hz, 1H-C(2)), (DMSO-d6) δ: 5.02 (s, 2H, OCH2), 7.32–7.36 (m, 1H, Ar-H),
7.24 (d, J=2.4Hz, 1H-C(4)), 7.42–7.50 (m, 3H, Ar-H), 7.43–7.47 (m, 2H, Ar-H), 7.55 (dd, J=8.8, 2.8Hz, 1H-C(3)),
7.63–7.69 (m, 2H, Ar-H), 7.83–7.88 (m, 3H, Ar-H), 7.91 (d, 7.65–7.67 (m, 4H, Ar-H), 7.72 (d, J=2.8Hz, 1H-C(1)), 7.74–7.76
J=8.8Hz, 1H-C(1)), 8.16–8.20 (m, 2H, Ar-H), 8.33–8.34 (m, (m, 2H, Ar-H), 7.90–7.95 (m, 2H, Ar-H), 8.19–8.22 (m,
1H, Ar-H), 10.44 (s, 1H, NH). 13C-NMR (DMSO-d6) δ: 67.44 2H, Ar-H), 8.22 (d, J=8.8Hz, 1H-C(4)), 10.35 (s, 1H, NH).
(CH2O), 101.62, 114.06, 115.44, 115.93, 118.00, 120.19, 121.22, 13C-NMR (DMSO-d6) δ: 67.91 (CH2O), 111.91, 120.76, 121.98,
124.44, 124.90, 125.95, 126.56, 127.39, 127.52, 127.76, 128.51, 126.98, 127.39, 127.45, 127.59, 127.68, 127.82, 129.61, 130.25,
130.01, 133.34, 135.19, 135.93, 155.67, 157.37, 163.58, 166.01 133.76, 134.94, 135.37, 135.70, 136.18, 138.41, 140.27, 163.29,
(C=O), 175.00. Anal. Calcd for C25H17NO4·0.25 H2O: C 75.09, 166.46 (C=O), 182.05, 183.08. Anal. Calcd. for C28H19NO4: C
H 4.41, N 3.50. Found: C 74.97, H 4.40, N 3.49.
77.59, H 4.42, N 3.23. Found: C 77.39, H 4.48, N 3.27.
2-(9H-Carbazol-2-yloxy)-N-(naphthalen-2-yl)acetamide (15):
2-(9-Oxo-9H-xanthen-3-yloxy)-N-phenylacetamide
(17a):