1680
M. I. Naumov et al.
PAPER
13C NMR (50 MHz, CDCl3): d = 14.1, 22.6, 27.6, 52.2, 55.3, 56.4,
61.4, 62.9, 96.8, 100.7, 101.7, 114.3, 121.0, 122.7, 133.0, 136.1,
137.5, 148.4, 149.0, 150.3, 157.3, 159.8, 162.3, 162.4.
Anal. Calcd for C24H23N3O4: C, 69.05; H, 5.55; N, 10.07. Found: C,
69.21; H, 5.57; N, 10.06.
4-{4¢-Methoxy-2¢-[(4¢¢-propyl-1H-1¢¢,2¢¢,3¢¢-triazol-1¢¢-yl)meth-
yl]phenyl}chromen-2-one (18c)
CC (eluent: EtOAc–PE, 3:2); polycrystalline colorless solid (86%);
Anal. Calcd for C25H27N3O7: C, 62.36; H, 5.65; N, 8.73. Found: C,
62.19; H, 5.67; N, 8.74.
mp 74–76 °C.
4-Hydroxy-3-(2¢-{[4¢¢-(1¢¢¢-hydroxycyclopentyl)-1H-1¢¢,2¢¢,3¢¢-
triazol-1¢¢-yl]methyl}-4¢-methoxyphenyl)-5,6,7-trimethoxy-
chromen-2-one (17b)
CC (eluent: EtOAc–EtOH, 9:1); polycrystalline colorless solid
(48%); mp 184 °C.
1H NMR (200 MHz, CDCl3): d = 1.74–2.00 (m, 8 H), 3.80 (s, 3 H),
3.87 (s, 3 H), 3.94 (s, 3 H), 4.18 (s, 3 H), 5.40 (d, J = 15.0 Hz, 1 H),
5.50 (d, J = 15.0 Hz, 1 H), 6.68 (s, 1 H), 6.85 (d, J = 2.7 Hz, 1 H),
6.98 (dd, J = 8.4, 2.7 Hz, 1 H), 7.23 (d, J = 8.4 Hz, 1 H), 7.39 (s, 1
H), 10.11 (s, 1 H).
13C NMR (50 MHz, CDCl3): d = 23.5, 23.6, 41.0, 41.3, 52.6, 55.4,
56.5, 61.4, 62.9, 78.8, 96.8, 100.7, 101.6, 114.3, 114.9, 119.9,
122.9, 133.3, 135.8, 137.5, 149.0, 150.3, 154.2, 157.3, 159.8, 162.2,
162.4.
1H NMR (200 MHz, CDCl3): d = 0.91 (t, J = 7.4 Hz, 3 H), 1.50–
1.69 (m, 2 H), 2.58 (t, J = 7.4 Hz, 2 H), 3.83 (s, 3 H), 5.24 (d,
J = 15.6 Hz, 1 H), 5.38 (d, J = 15.6 Hz, 1 H), 6.31 (s, 1 H), 6.81 (d,
J = 2.6 Hz, 1 H), 6.98–7.07 (m, 3 H), 7.16–7.23 (m, 2 H), 7.41 (d,
J = 7.4 Hz, 1 H), 7.50–7.57 (m, 1 H).
13C NMR (50 MHz, CDCl3): d = 13.7, 22.5, 27.5, 51.3, 55.5, 114.4,
114.6, 116.5, 117.3, 119.6, 120.7, 124.5, 126.0, 126.5, 130.5, 132.4,
134.4, 148.6, 153.7, 153.9, 160.2, 160.7.
Anal. Calcd for C22H21N3O3: C, 70.38; H, 5.64; N, 11.19. Found: C,
70.55; H, 5.60; N, 11.21.
4-{2¢-[(4¢¢-Acetyloxymethyl-1H-1¢¢,2¢¢,3¢¢-triazol-1¢¢-yl)methyl]-
4¢-methoxyphenyl}-5,7-dimethoxychromen-2-one (19a)
CC (eluent: EtOAc–PE, 7:3); polycrystalline colorless solid (91%);
mp 83 °C.
1H NMR (200 MHz, CDCl3): d = 2.05 (s, 3 H), 3.39 (s, 3 H), 3.81
(s, 3 H), 3.87 (s, 3 H), 5.11 (s, 2 H), 5.25 (d, J = 15.47 Hz, 1 H), 5.36
(d, J = 15.47 Hz, 1 H), 5.90 (s, 1 H), 6.20 (d, J = 2.0 Hz, 1 H), 6.52
(d, J = 2.0 Hz, 1 H), 6.70 (d, J = 2.0 Hz, 1 H), 6.89 (dd, J = 8.4, 1.8
Hz, 1 H), 7.09 (d, J = 8.4 Hz, 1 H), 7.31 (s, 1 H).
Anal. Calcd for C27H29N3O8: C, 61.94; H, 5.58; N, 8.03. Found: C,
61.89; H, 5.59; N, 8.00.
3-{2¢-[(4¢¢-Ethoxy-1H-1¢¢,2¢¢,3¢¢-triazol-1¢¢-yl)methyl]-4¢-meth-
oxyphenyl}-4-hydroxy-5,6,7-trimethoxychromen-2-one (17c)
CC (eluent: EtOAc); polycrystalline colorless solid (97%); mp
180 °C.
1H NMR (200 MHz, CDCl3): d = 1.34 (t, J = 7.1 Hz, 3 H), 3.77 (s,
3 H), 3.87 (s, 3 H), 3.94 (s, 3 H), 4.15 (q, J = 7.1 Hz, 2 H), 4.18 (s,
3 H), 5.28 (d, J = 15.2 Hz, 1 H), 5.42 (d, J = 15.2 Hz, 1 H), 6.69 (d,
J = 2.7 Hz, 1 H), 6.77 (s, 1 H), 6.93–6.95 (m, 2 H), 7.23 (d, J = 8.3
Hz, 1 H), 10.11 (s, 1 H).
13C NMR (50 MHz, CDCl3): d = 14.7, 53.1, 55.3, 56.4, 61.3, 62.9,
66.2, 96.7, 100.7, 101.6, 106.2, 114.3, 122.7, 133.0, 135.8, 137.5,
149.0, 150.3, 157.3, 159.8, 161.0, 162.3, 162.4.
13C NMR (50 MHz, CDCl3): d = 20.8, 51.7, 55.4, 55.8, 55.8, 57.5,
93.8, 95.8, 103.7, 113.0, 113.3, 113.6, 128.9, 131.5, 132.7, 153.1,
156.9, 157.9, 159.6, 160.3, 163.8, 170.8.
Anal. Calcd for C24H23N3O7: C, 61.93; H, 4.98; N, 9.03. Found: C,
61.77; H, 5.00; N, 8.99.
4-(2¢-{[4¢¢-(1¢¢¢-Hydroxycyclopentyl)-1H-1¢¢,2¢¢,3¢¢-triazol-1¢¢-
yl]methyl}-4¢-methoxyphenyl)-5,7-dimethoxychromen-2-one
(19b)
Anal. Calcd for C24H25N3O8: C, 59.62; H, 5.21; N, 8.69. Found: C,
59.80; H, 5.21; N, 8.66.
CC (eluent: EtOAc); polycrystalline colorless solid (47%); mp 88
°C.
4-{2¢-[(4¢¢-Acetyloxymethyl-1H-1¢¢,2¢¢,3¢¢-triazol-1¢¢-yl)methyl]-
4¢-methoxyphenyl}chromen-2-one (18a)
CC (eluent: EtOAc–PE, 7:3); polycrystalline colorless solid (71%);
mp 100 °C.
1H NMR (200 MHz, CDCl3): d = 2.05 (s, 3 H), 3.85 (s, 3 H), 5.08
(s, 2 H), 5.29 (d, J = 15.2 Hz, 1 H), 5.42 (d, J = 15.2 Hz, 1 H), 6.28
(s, 1 H), 6.86 (d, J = 2.2 Hz, 1 H), 7.00–7.04 (m, 2 H), 7.16–7.28
(m, 2 H), 7.35–7.42 (m, 2 H), 7.56 (dt, J = 7.9, 1.3 Hz, 1 H).
1H NMR (200 MHz, CDCl3): d = 1.76–2.08 (m, 8 H), 3.39 (s, 3 H),
3.82 (s, 3 H), 3.86 (s, 3 H), 5.23 (d, J = 15.1 Hz, 1 H), 5.34 (d,
J = 15.1 Hz, 1 H), 5.85 (s, 1 H), 6.19 (d, J = 2.4 Hz, 1 H), 6.52 (d,
J = 2.4 Hz, 1 H), 6.76 (d, J = 2.4 Hz, 1 H), 6.89 (dd, J = 8.3, 2.4 Hz,
1 H), 7.07 (d, J = 8.4 Hz, 1 H), 7.15 (s, 1 H).
13C NMR (50 MHz, CDCl3): d = 23.5, 23.5, 41.0, 41.1, 51.9, 55.4,
55.8, 55.8, 78.7, 93.8, 95.8, 103.8, 112.9, 113.1, 114.0, 120.0,
128.9, 131.6, 132.9, 153.2, 154.3, 156.9, 157.9, 159.6, 160.5, 163.7.
13C NMR (50 MHz, CDCl3): d = 20.8, 51.5, 57.8, 57.3, 114.4,
115.0, 116.5, 117.3, 119.4, 123.8, 124.5, 126.2, 126.4, 130.7, 132.1,
133.7, 143.1, 153.6, 153.7, 160.0, 160.7, 170.8.
Anal. Calcd for C26H27N3O6: C, 65.40; H, 5.70; N, 8.80. Found: C,
65.62; H, 5.72; N, 8.83.
4-{2¢-[(4¢¢-Acetyloxymethyl-1H-1¢¢,2¢¢,3¢¢-triazol-1¢¢-yl)methyl]-
4¢-methoxyphenyl}-5,6,7-trimethoxychromen-2-one (20a)
CC (eluent: EtOAc–PE, 7:3); polycrystalline colorless solid (85%);
mp 71–72 °C.
1H NMR (200 MHz, CDCl3): d = 2.05 (s, 3 H), 3.22 (s, 3 H), 3.80
(s, 6 H), 3.94 (s, 3 H), 5.14 (s, 2 H), 5.36 (s, 2 H), 5.95 (s, 1 H), 6.15
(m, 1 H), 6.59–6.79 (m, 2 H), 6.91 (dd, J = 8.4, 1.9 Hz, 1 H), 7.17
(d, J = 8.4 Hz, 1 H), 7.43 (s, 1 H).
Anal. Calcd for C22H19N3O5: C, 65.18; H, 4.72; N, 10.37. Found: C,
65.02; H, 4.70; N, 10.39.
4-(2¢-{[4¢¢-(1¢¢¢-Hydroxycyclopentyl)-1H-1¢¢,2¢¢,3¢¢-triazol-1¢¢-
yl]methyl}-4¢-methoxyphenyl)chromen-2-one (18b)
CC (eluent: EtOAc–PE, 7:3); polycrystalline colorless solid (85%);
mp 74 °C.
1H NMR (200 MHz, CDCl3): d = 1.78–1.93 (m, 8 H), 3.85 (s, 3 H),
5.26 (d, J = 15.4 Hz, 1 H), 5.38 (d, J = 15.4 Hz, 1 H), 6.24 (s, 1 H),
6.89 (d, J = 2.0 Hz, 1 H), 7.00–7.04 (m, 2 H), 7.15–7.23 (m, 3 H),
7.40 (d, J = 7.8 Hz, 1 H), 7.59 (dt, J = 8.5, 1.5 Hz, 1 H).
13C NMR (50 MHz, CDCl3): d = 20.8, 29.7, 51.9, 55.4, 56.3, 57.5,
61.1, 96.7, 107.4, 112.9, 113.7, 114.8, 123.9, 129.0, 130.5, 134.0,
139.6, 150.5, 151.4, 152.8, 157.3, 159.5, 160.0, 170.8.
13C NMR (50 MHz, CDCl3): d = 23.6, 23.7, 41.2, 41.3, 51.6, 55.5,
78.7, 114.4, 115.3, 116.5, 117.4, 119.6, 119.8, 124.5, 126.3, 126.5,
130.7, 132.4, 134.0, 153.7, 153.8, 160.2, 160.7.
Anal. Calcd for C25H25N3O8: C, 60.60; H, 5.09; N, 8.48. Found: C,
60.70; H, 5.08; N, 8.50.
Synthesis 2009, No. 10, 1673–1682 © Thieme Stuttgart · New York