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LETTER
DMSO-d6): d = 176.1, 173.9, 173.5, 164.5, 164.0, 136.8,
134.8, 133.1, 129.0, 128.6, 115.5, 40.7, 37.1, 28.5, 27.2 ppm.
Compound 7: mp 183–188 °C. 1H NMR (300 MHz, DMSO-
d6): d = 7.51 (d, 1 H, J = 7.03 Hz), 7.00 (s, 2 H), 5.76 (m, 1
H), 5.61 (d, 1 H, J = 7.33 Hz), 4.94 (m, 2 H), 3.57 (t, 2 H,
J = 7.04 Hz), 1.93 (q, 2 H, J = 7.04 Hz), 1.59 (pent, 2 H,
J = 7.03 Hz) ppm. 13C NMR (75 MHz, DMSO-d6): d =
166.5, 156.4, 146.6, 138.3, 115.7, 93.7, 48.8, 40.9, 30.7, 28.3
ppm.
+ H].
Compound 12: mp 236–240 °C. 1H NMR (300 MHz,
DMSO-d6): d = 10.70 (s, 2 H), 10.19 (s, 2 H), 8.41 (d, 4 H,
J = 7.16 Hz), 7.54 (m, 6 H), 5.57 (s, 2 H), 2.84 (m, 4 H), 2.30
(s, 4 H), 1.25 (s, 18 H) ppm. 13C NMR (75 MHz, DMSO-d6):
d = 176.1, 172.5, 172.0, 135.2, 132.6, 129.3, 128.6, 128.4,
36.8, 27.3, 26.5 ppm.
Compound 13: 1H NMR (300 MHz, DMSO-d6): d = 9.67 (s,
2 H), 8.87 (s, 2 H), 7.80 (d, 2 H, J = 6.9 Hz), 6.09 (s, 2 H),
5.34 (s, 2 H), 3.63 (s, 4 H), 3.08 (d, 4 H, J = 5.7 Hz), 1.91 (m,
4 H), 1.26 (m, 12 H), 0.80 (t, 6 H, J = 6.9 Hz) ppm. 13C NMR
(75 MHz, DMSO-d6): d = 162.4, 153.7, 148.5, 137.6, 115.3,
94.1, 49.0, 42.2, 31.5, 30.0, 27.3, 19.5, 13.6 ppm. HRMS: m/
z calcd 679.3469 [M + H]; found: 679.3397 [M + H].
Compound 14: mp 184–187 °C. 1H NMR (300 MHz,
DMSO-d6): d = 11.03 (s, 2 H), 9.62 (s, 2 H), 7.26 (m, 12 H),
5.23 (s, 2 H), 4.51 (s, 2 H), 3.99 (s, 4 H), 3.74 (s, 4 H), 3.06
(m, 4 H), 1.86 (s, 4 H), 1.65 (m, 10 H), 1.23 (s, 10 H), 0.81
(s, 6 H) ppm. 13C NMR (75 MHz, DMSO-d6): d = 172.0,
164.5, 157.0, 154.3, 146.9, 137.5, 129.8, 129.2, 128.2,
126.5, 97.3, 64.2, 55.5, 50.7, 37.2, 28.5, 22.2, 13.8, 0.96
ppm. HRMS: m/z calcd 529.3245 [M + H]; found: 529.3257
[M + H].
Compound 8: 1H NMR (300 MHz, DMSO-d6): d = 10.92 (s,
1 H), 8.99 (s, 1 H), 7.56 (s, 1 H), 7.42 (d, 1 H, J = 7.18 Hz),
5.79 (m, 1 H), 5.05, (m, 2 H), 3.83 (t, 2 H, J = 7.18 Hz), 3.25
(q, 2 H, J = 5.64 Hz), 2.12 (q, 2 H, J = 7.18 Hz), 1.86 (pent,
2 H, J = 7.44 Hz), 1.56 (pent, 2 H, J = 7.18 Hz), 1.38 (sext,
2 H, J = 7.95 Hz), 0.92 (t, 3 H, J = 7.43 Hz) ppm. 13C NMR
(75 MHz, DMSO-d6): d = 154.3, 149.9, 146.7, 136.8, 115.9,
97.3, 50.2, 39.7, 31.5, 30.4, 27.7, 20.1, 13.8 ppm. HRMS
(LSIMS+): m/z calcd: 278.1743; found: 279.1812 [M + H].
Compound 9: 1H NMR (300 MHz, DMSO-d6): d = 11.03 (s,
1 H), 9.72 (s, 1 H), 7.41 (s, 1 H), 7.40 (d, 1 H, J = 7.30 Hz),
7.26 (m, 5 H), 5.74 (m, 1 H), 4.96 (m, 2 H), 4.59 (q, 1 H,
J = 6.43 Hz), 4.09 (t, 2 H, J = 6.57 Hz), 3.15 (m, 2 H), 2.02
(q, 2 H, J = 7.89, 6.43 Hz), 1.67 (m, 5 H), 1.31 (m, 5 H), 0.88
(t, 3 H, J = 6.72 Hz) ppm. 13C NMR (75 MHz, DMSO-d6): d
= 172.2, 164.7, 154.3, 146.7, 137.5, 129.2, 128.3, 126.6,
115.1, 97.3, 64.4, 55.3, 50.8, 37.3, 29.9, 27.7, 22.3, 13.9
ppm.
Compound 15: mp 230–235 °C. 1H NMR (300 MHz,
CDCl3): d = 10.89 (br s, 1 H), 9.04 (s, 1 H), 8.81 (s, 2 H),
8.43 (d, 2 H, J = 7.31 Hz), 5.53 (m 3 H), 3.80 (m, 2 H), 3.09
(t, 2 H, J = 7.01 Hz), 2.48 (q, 2 H, J = 7.16 Hz), 2.05 (m, 2
H), 1.81 (p, 2 H, J = 7.02), 1.52 (m, 1 H), 1.36 (s, 9 H), 1.26–
1.16 (m, 5 H), 0.90 (t, 3 H, J = 7.46) ppm. 13C NMR (75
MHz, CDCl3): d = 176.6, 174.2, 173.7, 164.8, 154.1, 147.1,
135.1, 133.3, 130.1, 130.0, 129.2, 128.8, 66.1, 54.2, 50.4,
47.8, 40.9, 37.9, 29.6, 28.4, 27.8, 27.4, 24.5, 20.5, 15.5, 10.9
ppm.
Compound 11: [a]20 –59.0; mp 110–112 °C. 1H NMR (300
MHz, DMSO-d6): d = 11.03 (s, 2 H), 9.62 (s, 2 H), 7.26 (m,
12 H), 5.23 (s, 2 H), 4.51 (s, 2 H), 3.99 (s, 4 H), 3.74 (s, 4 H),
3.06 (m, 4 H), 1.86 (s, 4 H), 1.65 (m, 10 H), 1.23 (s, 10 H),
0.81 (s, 6 H) ppm. 13C NMR (75 MHz, DMSO-d6): d =
172.0, 164.5, 157.0, 154.3, 146.9, 137.5, 129.8, 129.2,
128.2, 126.5, 97.3, 64.2, 55.5, 50.7, 37.2, 28.5, 22.2, 13.8,
0.96 ppm. HRMS: m/z calcd: 440.2424; found: 441.2502 [M
(11) Shie, J.-J.; Fang, J.-F. J. Org. Chem. 2002, 68, 1158.
Synlett 2008, No. 2, 203–206 © Thieme Stuttgart · New York