Molecules 2021, 26, 3617
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1H), 5.75 (dd, J = 9.9, 3.3 Hz, 1H). 13C NMR (75 MHz, CDCl3)
δ
(ppm) 148.59, 139.92, 134.89,
132.57, 129.64, 128.43, 127.71, 126.74 (q, J = 30 Hz), 126.59, 125.97 (q, J = 2.1 Hz), 125.68,
124.69, 124.65, 123.03, 122.14, 120.74, 115.10, 73.71. HRMS (ESI) calcd for [C20H13F3O + H]+:
327.0997, found: 327.0999.
2-(4-Methoxyphenyl)-2H-benzo[h]chromene (3h). The title compound was prepared
according to the general procedure: 17 h; red oil; 84% yield; 1H NMR (300 MHz, CDCl3)
δ
(ppm) 8.20–8.17 (m, 1H), 7.76–7.72 (m, 1H), 7.49–7.37 (m, 5H), 7.19 (d, J = 8.4 Hz,1H),
6.93–6.88 (m, 2H), 6.69 (dd, J = 9.8, 1.8 Hz, 1H), 6.10 (dd, J = 3.9, 1.8 Hz, 1H), 5.88 (dd,
J = 9.8, 3.6 Hz, 1H), 3.79 (s, 3H). 13C NMR (75 MHz, CDCl3)
(ppm) 159.82, 148.58, 134.73,
δ
133.23, 128.56, 127.68, 126.35, 125.48, 124.76, 124.67, 123.44, 122.13, 120.39, 115.85, 114.11,
77.02, 55.36. HRMS (ESI) calcd for [C20H16O2 + H]+: 289.1229, found: 289.1235.
2-(2-Methoxyphenyl)-2H-benzo[h]chromene (3i). The title compound was prepared
according to the general procedure: 24 h; red oil; 80% yield; 1H NMR (300 MHz, CDCl3)
δ
(ppm) 8.22–8.18 (m, 1H), 7.76–7.53 (m, 1H), 7.51 (dd, J = 7.5, 1.5 Hz, 1H), 7.45–7.39 (m,
2H), 7.37 (d, J = 8.1 Hz, 1H), 7.31–7.25 (m, 1H), 7.16 (d, J = 8.4 Hz, 1H), 6.95–6.89 (m, 2H),
6.58 (dd, J = 9.6, 1.8 Hz, 1H), 6.53 (dd, J = 3.6, 1.8 Hz, 1H), 5.90 (dd, J = 9.9, 3.6 Hz, 1H).
13C NMR (75 MHz, CDCl3)
δ (ppm) 155.82, 149.02, 134.71, 129.81, 129.14, 127.73, 127.52,
126.28, 125.50, 124.80, 124.62, 123.78, 123.73, 122.16, 120.94, 120.31, 115.66, 110.70, 72.54,
55.65. HRMS (ESI) calcd for [C20H16O2 + H]+: 289.1229, found: 289.1230.
4-(2H-Benzo[h]chromen-2-yl)-N,N-dimethylaniline (3j). The title compound was pre-
pared according to the general procedure, except that the mixture was stirred at room
temperature: 36 h; purple oil; 54% yield; 1H NMR (300 MHz, CDCl3)
δ
(ppm) 8.18–8.14 (m,
1H), 7.3–7.70 (m, 1H), 7.43–7.33 (m, 5H), 7.18 (d, J = 8.4 Hz, 1H), 6.73–6.66 (m, 3H), 6.06 (dd,
J = 3.9, 1.8 Hz, 1H), 5.87 (dd, J = 9.6, 3.6 Hz, 1H), 2.94 (s, 6H). 13C NMR (75 MHz, CDCl3)
δ
(ppm) 150.80, 148.73, 134.65, 128.56, 128.48, 127.61, 126.22, 125.33, 124.84, 124.72, 124.43,
123.73, 122.27, 120.13, 115.92, 112.43, 77.41, 40.59. HRMS (ESI) calcd for [C21H19NO + H]+:
302.1545, found: 302.1544.
4-(2H-Benzo[h]chromen-2-yl)-2-methoxyphenyl acetate (3k). The title compound was
prepared according to the general procedure: 46 h; red oil; 99% yield; 1H NMR (300 MHz,
CDCl3)
7.10–7.00 (m, 2H), 6.66 (dd, J = 9.9, 1.8 Hz, 1H), 6.10 (dd, J = 3.6, 1.8 Hz, 1H), 5.87 (dd,
J = 9.6, 3.6 Hz, 1H), 3.79 (s, 3H), 2.31 (s, 3H). 13C NMR (75 MHz, CDCl3)
(ppm) 169.15,
δ (ppm) 8.20–8.17 (m, 1H), 7.75–7.72 (m, 1H), 7.44–7.36 (m, 3H), 7.19–7.16 (m, 2H),
δ
151.28, 148.54, 140.16, 139.70, 134.76, 127.78, 126.50, 125.67, 124.91, 124.68, 124.62, 123.25,
122.93, 122.01, 120.71, 119.16, 115.85, 111.09, 76.97, 55.99, 20.81. HRMS (ESI) calcd for
[C22H18O4 + H]+: 347.1283, found: 347.1283.
4-(2H-benzo[h]chromen-2-yl)-2-methoxyphenol (3l). The title compound was pre-
1
pared according to the general procedure: 68 h; red oil; 77% yield; H NMR (300 MHz,
CDCl3)
δ (ppm) 8.19–8.16 (m, 1H), 7.76–7.72 (m, 1H), 7.45–7.36 (m, 3H), 7.19 (d, J = 8.1 Hz,
1H), 7.09–7.01 (m, 2H), 6.91 (d, J = 8.1 Hz, 1H), 6.68 (dd, J = 9.9, 1.8 Hz, 1H), 6.06 (dd,
J = 3.3, 1.5 Hz, 1H), 5.87 (dd, J = 9.9, 3.6 Hz, 1H), 5.68 (s, 1H), 3.84 (s, 3H). 13C NMR
(75 MHz, CDCl3)
δ 148.56, 146.69, 145.90, 134.70, 133.05, 127.71, 126.38, 125.50, 124.79,
124.67, 123.53, 122.06, 120.46, 120.42, 115.88, 114.39, 109.82, 77.32, 55.99. HRMS (ESI) calcd
for [C20H16O3 + H]+: 305.1178, found: 305.1177.
6-Chloro-2-phenyl-2H-benzo[h]chromene (3m). The title compound was prepared
according to the general procedure: 46 h; red oil; 81% yield; 1H NMR (300 MHz, CDCl3)
δ
(ppm) 1H NMR (300 MHz, CDCl3)
δ
8.22–8.13 (m, 2H), 7.57–7.45 (m, 5H), 7.41–7.33 (m,
3H), 7.29 (s, 1H), 6.60 (dd, J = 9.9, 1.8 Hz, 1H), 6.13 (dd, J = 3.6, 1.8 Hz, 1H), 5.91 (dd, J = 9.9,
3.6 Hz, 1H). 13C NMR (75 MHz, CDCl3)
(ppm) 147.64, 140.68, 131.40, 128.81, 128.58,
δ
127.47, 126.93, 126.29, 125.74, 124.48, 124.17, 123.75, 123.43, 122.47, 116.09, 77.46. HRMS
(ESI) calcd for [C19H13ClO + H]+: 293.0733, found: 293.0735.
6-Bromo-2-phenyl-2H-benzo[h]chromene (3n). The title compound was prepared
according to the general procedure, except that 50-mg 4Å MS powder was added: 72 h;
red oil; 60% yield; 1H NMR (300 MHz, CDCl3)
δ
(ppm) 8.21–8.09 (m, 2H), 7.57–7.43 (m,
5H), 7.41–7.30 (m, 3H), 6.60 (dd, J = 9.9, 1.5 Hz, 1H), 6.14 (dd, J = 3.3, 1.5 Hz, 1H), 5.90