7.38‒7.39 (m, 1H), 7.49 (s, 1H), 7.48‒7.53 (m, 1H), 8.09 (d, J =
12.4 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ (ppm) 55.4,
106.1, 116.3, 117.8, 123.8, 130.3, 133.0, 149.5, 152.8, 160.1,
171.9; MS (EI) m/z 107 (100%), 256 (M+); HRMS Calcd. for
C14H12N2O3: 256.0849, Found 256.0846, Anal. Calcd. for
C14H12N2O3: C 65.61, H 4.72, N 10.93 Found: C 65.36, H 4.71,
N 10.93
133.0, 148.4, 149.6, 162.6, 165.1, 171.9; MS (EI) m/z 95 (100%),
244 (M+); HRMS Calcd. for C13H9FN2O2: 244.0648, Found:
244.0655; Anal. Calcd. for C13H9FN2O2 · 0.1 H2O: C 63.46, H
3.77, N 11.39, Found: C 63.36, H 3.77, N 11.33.
4.1.13. (E)-5-(4-Methoxyphenyl)-2-
hydroxycyclohepta-2,4,6-trienone (1m)
Compound 1m was prepared by the same method as
described for the synthesis of 1a using p-anisidine (247 mg, 2.0
mmol) instead of aniline; 77 mg (15% yield); brown needles
4.1.9. (E)-5-(3-Cyanophenyl)-2-hydroxycyclohepta-
2,4,6-trienone (1i)
1
(AcOEt); mp 170‒174 °C; H NMR (400 MHz, DMSO-d6) δ
(ppm) 3.86 (s, 3H) 7.13 (d, J = 9.1 Hz, 2H), 7.35 (d, J = 12.2 Hz,
2H), 7.87 (d, J = 9.1 Hz, 2H), 8.05 (d, J = 12.0 Hz, 2H); 13C
NMR (100 MHz, DMSO-d6) δ (ppm) 55.7, 114.7, 123.9, 124.7,
132.4, 145.9, 149.7, 162.1, 171.7; MS (EI) m/z 107 (100%), 256
(M+); HRMS Calcd. for C14H12N2O3: 256.0848, Found:
256.0846; Anal. Calcd. for C14H12N2O3: C 65.62, H 4.72, N
10.93, Found: C 65.34, H 4.65, N 10.80.
Compound 1i was prepared by the same method as described
for the synthesis of 1a using 3-aminobenzonitrile (236 mg, 2.0
mmol) instead of aniline; 63 mg (13% yield); red needles
1
(AcOEt); mp 199‒201 °C; H NMR (400 MHz, DMSO-d6) δ
(ppm) 7.36 (d, J = 12.2 Hz, 2H), 7.79 (t, J = 8.0 Hz, 1H), 8.01 (d,
J = 7.6 Hz, 1H), 8.12 (d, J = 12.0 Hz, 2H), 8.16 (d, J = 1.9 Hz,
1H), 8.26 (t, J = 1.7 Hz, 1H), 13C NMR (100 MHz, DMSO-d6) δ
(ppm) 112.6, 118.1, 123.8, 126.0, 127.1, 131.0, 133.5, 134.5,
149.3, 151.5, 172.4; MS (EI) m/z 251 (M+, 100%); HRMS Calcd.
for C14H9N3O2: 251.0695, Found: 251.0691; Anal. Calcd. for
C14H9N3O2: C 66.93, H 3.61, N 16.73, Found: C 66.63, H 3.68,
N 16.64.
4.1.14. (E)-5-(4-Nitrophenyl)-2-hydroxycyclohepta-
2,4,6-trienone (1n)
Compound 1n was prepared by the same method as described
for the synthesis of 1a using 4-nitroaniline (558 mg, 4.0 mmol)
instead of aniline; 55 mg (10% yield); brown needles (AcOEt);
1
mp 250‒254 °C; H NMR (270 MHz, DMSO-d6) δ (ppm) 7.26
4.1.10. (E)-5-(3-Nitrophenyl)-2-hydroxycyclohepta-
2,4,6-trienone (1j)
(d, J = 12.0 Hz, 2H), 8.01 (d, J = 9.1 Hz, 2H), 8.1 (d, J = 9.1 Hz,
2H), 8.41 (d, J = 12.0 Hz, 2H); 13C NMR (100 MHz, DMSO-d6)
δ (ppm) 122.9, 123.8, 125.2, 133.8, 147.8, 154.5, 173.8; MS (EI)
m/z 271 (M+, 100%); HRMS Calcd. for C13H9N3O4: 271.0593,
Found: 271.0596; Anal. Calcd. for C13H9N3O4: C 57.57, H 3.34,
N 15.49, Found: C 57.46, H 3.35, N 15.23.
Compound 1j was prepared by the same method as described
for the synthesis of 1a using 3-nitroaniline (277 mg, 2.0 mmol)
instead of aniline; 301 mg (55% yield); red/brown needles
1
(AcOEt); mp 231–232 °C; H NMR (400 MHz, DMSO-d6) δ
(ppm) 7.35 (d, J = 11.6 Hz, 2H), 7.89 (t, J = 8.0 Hz, 1H), 8.15 (d,
J = 11.6 Hz, 2H), 8.31 (d, J = 7.6 Hz, 1H), 8.39 (d, J = 7.2 Hz,
1H), 8.52 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ (ppm)
115.5, 123.7, 125.2, 129.6, 131.1, 133.6, 148.7, 151.8, 152.4,
172.4; MS (EI) m/z 271 (M+, 100%); HRMS Calcd. for
C13H9N3O4: 271.0594, Found: 271.0597; Anal. Calcd. for
C13H9N3O4 · 0.1 H2O: C 57.18, H 3.40, N 15.39, Found: C 57.10,
H 3.24, N 15.78.
4.1.15. (E)-5-(4-Ethoxycarbonylphenyl)-2-
hydroxycyclohepta-2,4,6-trienone (1o)
Compound 1o was prepared by the same method as described
for the synthesis of 1a using ethyl 4-amionobenzoate (331 mg,
2.0 mmol) instead of aniline; 11 mg (2% yield); red needles
1
(AcOEt); mp 208‒210 °C; H NMR (400 MHz, DMSO-d6) δ
(ppm) 1.34 (t, J = 7.1 Hz, 3H), 4.34 (q, J = 7.1 Hz, 2H), 7.33 (d,
J = 11.9 Hz, 2H), 7.95 (d, J = 8.5 Hz, 2H), 8.12 (d, J = 12.0 Hz,
2H), 8.14 (d, J = 8.3 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ
(ppm) 14.1, 61.1, 122.6, 123.8, 130.5, 131.5, 133.5, 149.4, 153.9,
165.1, 172.5; MS (EI) m/z 149 (100%), 298 (M+); HRMS Calcd.
for C16H14N2O4: 298.0954, Found: 298.0958; Anal. Calcd. for
C16H14N2O4: C 64.42, H 4.73, N 9.39, Found: C 64.35, H 4.72, N
9.28.
4.1.11. (E)-5-(3-Methoxycarbonylphenyl)-2-
hydroxycyclohepta-2,4, 6-trienone (1k)
Compound 1k was prepared by the same method as described
for the synthesis of 1a using methyl 3-aminobanzoate (604 mg,
4.0 mmol) instead of aniline; 203 mg (36% yield): brown thin
needles (AcOEt); mp 202‒206 °C; 1H NMR (400 MHz, DMSO-
d6) δ (ppm) 3.88 (s, 3H), 7.36 (d, J = 12.0 Hz, 2H), 7.74 (t, J =
7.8 Hz, 1H), 8.11‒8.15 (m, 4H), 8.33 (d, J = 1.7 Hz, 1H), 13C
NMR (100 MHz, DMSO-d6) δ (ppm) 52.5, 122.5, 123.8, 127.8,
130.3, 131.0, 131.6, 133.3, 149.5, 151.5, 165.6, 172.1; MS (EI)
m/z 135 (100%), 284 (M+); HRMS Calcd. for C15H12N2O4:
284.0797, Found: 284.0798; Anal. Calcd. for C15H12N2O4: C
63.38, H 4.25, N 9.85, Found: C 62.75, H 4.24, N 9.73.
4.1.16. (E)-5-(2-Methyl-3-nitrophenyl)diazenyl)-2-
hydroxycyclohepta-2,4,6-trienone (1p)
Compound 1p was prepared by the same method as described
for the synthesis of 1a using 2-methyl-3-nitroaniline (312 mg,
2.1 mmol) instead of aniline; 34 mg (6% yield); brown prisms
1
(AcOEt); mp 176–178 °C; H NMR (400 MHz, DMSO-d6) δ
(ppm) 2.78 (s, 3H), 7.38 (d, J = 11.6 Hz, 2H), 7.58 (t, J = 7.6 Hz,
8.4 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 8.08 (d, J = 8.4 Hz, 1H),
8.15 (d, J = 12.0 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ
(ppm) 12.7, 119.9, 123.8, 126.3, 127.5, 131.3, 133.7, 149.9,
150.5, 151.1, 172.2; MS (EI) m/z 121 (100%), 285 (M+); HRMS
Calcd. for C14H11N3O4: 285.0750, Found: 285.0754; Anal. Calcd.
for C14H11N3O4 · 0.1 H2O: C 58.57, H 3.93, N 14.64, Found: C
58.18, H 3.81, N 14.51.
4.1.12. (E)-5-(4-Fluorophenyl)-2-
hydroxycyclohepta-2,4, 6-trienone (1l)
Compound 1l was prepared by the same method as described
for the synthesis of 1a using 4-fluoroaniline (243 mg, 2.2 mmol)
instead of aniline; 152 mg (33% yield); yellow/brown plates
1
(AcOEt); mp 201‒202 °C; H NMR (400 MHz, DMSO-d6) δ
(ppm) 7.36 (d, J = 12.0 Hz, 2H), 7.43 (t, J = 8.8 Hz, 2H), 7.94
(dt, J = 5.4 Hz, 9.0 Hz, 2H), 8.08 (d, J = 12.0 Hz, 2H); 13C NMR
(100 MHz, DMSO-d6) δ (ppm) 116.4, 116.7, 123.9, 124.9, 125.0,