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4-Hydroxy-5-nicotinoylcyclohepta-2,4,6-trien-1-one 3j. Yellow 1.27 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ = 200.5,
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solid, m.p. 236–238 °C. H NMR (400 MHz, CDCl3): δ = 15.79 186.4, 175.6, 145.8, 135.6, 135.1, 129.5, 114.2, 104.7, 64.7, 15.2.
(brs, 1H), 8.87–8.83 (m, 2H), 7.94 (d, J = 8.0 Hz, 1H), 7.50 (dd, J HRMS (ESI) m/z: [M + H]+ calcd for C13H17O5, 253.1076; found,
= 7.6, 4.8 Hz, 1H), 7.27 (d, J = 12.8 Hz, 1H), 7.21–7.16 (m, 2H), 253.1072.
6.53 (dd, J = 12.8, 2.0 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ =
4-(Cyclopropanecarbonyl)-5-hydroxycyclohepta-2,4,6-trien-1-
200.2, 186.1, 175.5, 152.9, 149.4, 146.2, 136.4, 135.1, 133.2, one 3r. Yellow oil.19b 1H NMR (400 MHz, CDCl3): δ = 16.30 (s,
129.3, 123.5, 115.8. HRMS (ESI) m/z: [M + H]+ calcd for 1H), 7.78 (d, J = 12.8 Hz, 1H), 7.12–7.06 (m, 2H), 6.64 (d, J =
C13H10NO3, 228.0661; found, 228.0664.
12.8 Hz, 1H), 2.58–2.51 (m, 1H), 1.39–1.33 (m, 2H), 1.24–1.18
(m, 2H). 13C NMR (100 MHz, CDCl3): δ = 206.6, 186.0, 173.5,
4-Hydroxy-5-(2-methoxybenzoyl)cyclohepta-2,4,6-trien-1-one
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3k. Yellow solid, m.p. 129–131 °C. H NMR (400 MHz, CDCl3): 145.0, 135.8, 135.0, 129.6, 116.7, 17.8, 13.3.
δ = 15.95 (s, 1H), 7.48–7.42 (m, 1H), 7.25 (dd, J = 7.4, 1.4 Hz,
4-(Cyclohexanecarbonyl)-5-hydroxycyclohepta-2,4,6-trien-1-
1H), 7.09–6.99 (m, 4H), 6.93 (d, J = 8.4 Hz, 1H), 6.37 (dd, J = one 3s. Yellow solid, m.p. 89–91 °C. 1H NMR (400 MHz,
12.8, 2.4 Hz, 1H), 3.72 (s, 3H). 13C NMR (100 MHz, CDCl3): δ = CDCl3): δ = 16.55 (s, 1H), 7.45 (d, J = 12.8 Hz, 1H), 7.07–6.99
203.1, 186.0, 174.2, 156.1, 145.7, 138.2, 135.4, 132.9, 129.0, (m, 2H), 6.56 (dd, J = 12.8, 2.0 Hz, 1H), 3.15–3.09 (m, 1H),
128.9, 126.9, 121.2, 117.3, 111.4, 55.7. HRMS (ESI) m/z: [M + 1.86–1.71 (m, 5H), 1.53–1.28 (m, 5H). 13C NMR (100 MHz,
H]+ calcd for C15H13O4, 257.0814; found, 257.0819.
CDCl3): δ = 210.9, 186.1, 175.1, 145.1, 136.0, 134.4, 129.5,
4-(1-Naphthoyl)-5-hydroxycyclohepta-2,4,6-trien-1-one 3l. Yellow 114.9, 45.9, 29.5, 25.7, 25.6. HRMS (ESI) m/z: [M + H]+ calcd for
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solid, m.p. 228–229 °C. H NMR (400 MHz, CDCl3): δ = 16.37 C14H17O3, 233.1178; found, 233.1179.
(s, 1H), 8.04 (d, J = 8.0 Hz, 1H), 7.97–7.94 (m, 1H), 7.78 (d, J =
2-Benzoyl-5-methylcyclohepta-2,4,6-trienone
5a.
Yellow
7.6 Hz, 1H), 7.62–7.48 (m, 4H), 7.24 (d, J = 13.2 Hz, 1H), 7.16 solid, m.p. 74–75 °C (ref. 19b m.p. 75–76 °C). 1H NMR
(dd, J = 13.2, 2.4 Hz, 1H), 7.07 (d, J = 12.8 Hz, 1H), 6.32 (dd, J = (400 MHz, CDCl3): δ = 7.83 (d, J = 7.6 Hz, 2H), 7.52 (t, J = 7.4
13.0, 2.6 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ = 204.8, 186.0, Hz, 1H), 7.40 (t, J = 7.6 Hz, 2H), 7.18 (d, J = 8.8 Hz, 1H), 7.12
175.5, 146.2, 137.5, 135.4, 134.9, 133.5, 131.5, 129.7, 129.2, (dd, J = 12.4, 1.6 Hz, 1H), 7.04 (d, J = 12.4 Hz, 1H), 6.93 (d, J =
128.8, 127.8, 127.0, 126.1, 124.7, 117.2, 116.1. HRMS (ESI) m/z: 9.2 Hz, 1H), 2.35 (s, 3H). 13C NMR (100 MHz, CDCl3): δ =
[M + H]+ calcd for C18H13O3, 277.0865; found, 277.0867.
196.4, 185.4, 148.9, 148.1, 142.1, 140.0, 135.9, 135.7, 133.4,
4-Hydroxy-5-pentanoylcyclohepta-2,4,6-trien-1-one
3m. 132.0, 129.3, 128.6, 26.5.
Yellow oil.19b 1H NMR (400 MHz, CDCl3): δ = 16.23 (s, 1H),
2-Benzoyl-5-phenylcyclohepta-2,4,6-trien-1-one 5b. Yellow
7.41 (d, J = 12.8 Hz, 1H), 6.98–6.91 (m, 2H), 6.48 (dd, J = 13.0, solid, m.p. 131–132 °C (ref. 19b m.p. 130–132 °C). 1H NMR
2.2 Hz, 1H), 2.86 (t, J = 7.4 Hz, 2H), 1.65–1.57 (m, 2H), (400 MHz, CDCl3): δ = 7.91–7.87 (m, 2H), 7.58–7.40 (m, 10H),
1.36–1.28 (m, 2H), 0.87 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, 7.27–7.22 (m, 2H). 13C NMR (100 MHz, CDCl3): δ = 196.2,
CDCl3): δ = 207.9, 185.8, 174.0, 145.0, 135.6, 134.6, 129.5, 185.2, 149.9, 149.6, 142.9, 141.4, 138.2, 135.9, 135.6, 133.6,
115.8, 39.1, 26.5, 22.2, 13.7.
131.9, 129.4, 129.3, 129.2, 128.7, 127.5.
4-Hydroxy-5-(4-phenylbutanoyl)cyclohepta-2,4,6-trien-1-one
2-Benzoyl-4-chloro-5-methylcyclohepta-2,4,6-trienone
5c.
3n. Brown oil. 1H NMR (400 MHz, CDCl3): δ = 16.29 (s, 1H), Colorless oil. 1H NMR (400 MHz, CDCl3): δ = 7.85–7.82 (m,
7.38–7.31 (m, 3H), 7.26–7.21 (m, 3H), 7.10 (s, 2H), 6.57 (d, J = 2H), 7.57 (t, J = 7.6 Hz, 1H), 7.47–7.41 (m, 3H), 7.20 (d, J = 12.8
13.2 Hz, 1H), 2.94 (t, J = 7.4 Hz, 2H), 2.76 (t, J = 7.4 Hz, 2H), Hz, 1H), 6.99 (d, J = 12.8 Hz, 1H), 2.49 (s, 3H). 13C NMR
2.15–2.06 (m, 2H). 13C NMR (100 MHz, CDCl3): δ = 207.5, (100 MHz, CDCl3): δ = 194.9, 183.9, 147.3, 143.6, 139.8, 139.5,
186.0, 174.1, 145.2, 140.9, 135.7, 134.5, 129.6, 128.6, 128.5, 138.6, 138.3, 135.4, 133.8, 129.4, 128.7, 26.1. HRMS (ESI) m/z:
126.3, 115.9, 38.5, 34.9, 25.9. HRMS (ESI) m/z: [M + H]+ calcd [M + H]+ calcd for C15H12ClO2, 259.0526; found, 259.0525.
for C17H17O3, 269.1178; found, 269.1177.
(11-Hydroxydibenzo[b,f]oxepin-10-yl)(phenyl)methanone
4-Hydroxy-5-(2-methoxyacetyl)cyclohepta-2,4,6-trien-1-one
5d. Yellow solid, m.p. 169–171 °C (ref. 19b m.p. 170–172 °C).
3o. Yellow oil.19b 1H NMR (400 MHz, C6D6): δ = 15.93 (s, 1H), 1H NMR (400 MHz, CDCl3): δ = 7.95 (dd, J = 8.0, 1.6 Hz, 1H),
6.68 (d, J = 13.2 Hz, 1H), 6.45–6.37 (m, 3H), 3.71 (s, 2H), 3.01 7.54–7.45 (m, 3H), 7.37 (t, J = 7.4 Hz, 1H), 7.31–7.22 (m, 5H),
(s, 3H). 13C NMR (100 MHz, C6D6): δ = 202.9, 185.0, 173.8, 7.14–7.09 (m, 1H), 6.77–6.73 (m, 1H), 6.65 (dd, J = 7.8, 1.4 Hz,
145.3, 134.0, 132.0, 129.8, 114.1, 74.3, 58.6.
1H). 13C NMR (100 MHz, CDCl3): δ = 193.5, 178.8, 161.2, 158.2,
4-(2-(Benzyloxy)acetyl)-5-hydroxycyclohepta-2,4,6-trien-1-one
3p. Yellow oil. H NMR (400 MHz, CDCl3): δ = 15.70 (brs, 1H), 127.9, 125.3, 124.6, 120.9, 120.8, 111.4.
137.4, 134.2, 132.9, 131.4, 130.4, 129.8, 128.8, 128.2, 128.1,
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7.38–7.31 (m, 5H), 7.29 (d, J = 13.2 Hz, 1H), 7.09 (s, 2H), 6.56
10-Benzoyl-11-hydroxy-10,11-dihydro-5H-dibenzo[a,d][7]
(d, J = 12.8 Hz, 1H), 4.67 (s, 2H), 4.63 (s, 2H). 13C NMR annulen-5-one 5e. Yellow solid, m.p. 125–127 °C (ref. 19b
(100 MHz, CDCl3): δ = 202.9, 186.1, 174.3, 145.6, 136.5, 135.5, m.p. 126–128 °C). 1H NMR (400 MHz, CDCl3): δ = 16.75 (s,
133.7, 130.0, 128.7, 128.4, 128.2, 116.2, 73.8, 72.5. HRMS (ESI) 1H), 8.26–8.23 (m, 1H), 7.79–7.76 (m, 1H), 7.70–7.62 (m, 3H),
m/z: [M + H]+ calcd for C16H15O4, 271.0970; found, 271.0967.
4-(2,2-Diethoxyacetyl)-5-hydroxycyclohepta-2,4,6-trien-1-one
7.34–7.28 (m, 3H), 7.26–7.18 (m, 3H), 7.01 (t, J = 7.0 Hz, 1H),
6.83 (d, J = 7.6 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ = 197.7,
3q. Yellow oil. 1H NMR (400 MHz, CDCl3): δ = 15.49 (s, 1H), 197.1, 174.9, 142.4, 141.5, 138.1, 132.7, 132.5, 132.2, 131.9,
8.01 (d, J = 13.2 Hz, 1H), 7.13–7.06 (m, 2H), 6.60 (dd, J = 13.0, 131.7, 131.5, 129.7, 129.6, 129.5, 128.0, 127.3, 127.1, 126.7,
1.0 Hz, 1H), 5.10 (s, 1H), 3.87–3.78 (m, 2H), 3.69–3.60 (m, 2H), 112.3.
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Dalton Trans.