The Journal of Organic Chemistry
Page 16 of 23
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.7 Hz, 1H), 4.08 (t, J = 4.8 Hz, 1H), 3.98 (d, J = 7.5 Hz, 3H), 3.79 (d, J = 11.7 Hz), 3.68 (d, J
12.3 Hz, 1H); 13C{ H} NMR (100 MHz, DMSO-d
1
) δ 162.4, 162.0, 161.3, 159.6, 159.0,
=
6
1
1
49.6, 148.9, 148.8, 139.1, 136.6, 136.6, 133.1, 133.0, 119.5, 119.4, 113.6, 113.41, 113.1,
12.9, 108.1, 88.9, 84.9, 74.3, 69.7, 60.5, 32.4; HR-ESI MS (m/z): [M + H]+ calcd for
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C
19
H
17FN
3
O
6
S 434.0817, found 434.0840.
5
-(6-Methoxy-8H-indeno[1,2-d]thiazol-2-yl)-1-(β-D-ribofuranosyl)–uracil (7d).
Compound 7d (258 mg, 75%) was obtained as a light yellow solid. TLC (silica gel, CH
2
Cl
2
/MeOH,
1
5
1
:1) R
f
0.54; UV (MeOH): λmax 351 nm (15100); H NMR (400 MHz, DMSO-d
6
) δ 11.98 (br s,
H), 9.08 (s, 1H), 7.65 (d, J = 8.3 Hz, 1H), 7.20 (d, J = 2.3 Hz, 1H), 6.96 (dd, J = 8.3 Hz, 2.4
Hz, 1H), 5.92 (d, J = 4.7 Hz, 1H), 5.51 (br s, 1H), 5.26 (t, J = 4.5 Hz, 1H), 5.17 (br s, 1H), 4.20
(
d, J = 5.1 Hz, 1H), 4.08 (t, J = 4.8 Hz, 1H), 3.98 (dd, J = 4.8 Hz, 2.8 Hz, 1H), 3.90 (s, 2H),
3 6
.83 – 3.74 (m, 4H, CH ) δ 161.8,
), 3.72 – 3.64 (m, 1H); 13C{ H} NMR (100 MHz, DMSO-d
1
3
161.19, 159.9, 157.9, 149.5, 148.3, 138.7, 134.8, 129.6, 119.1, 112.3, 111. 7, 108.3, 88.8, 84.9,
+
74.2, 69.8, 60.6, 55.3, 32.2; HR-ESI MS (m/z): [M + H] calcd for C20
H
20
N
3
O
7
S 446.1016,
found 446.1029.
5-(5-Methoxy-8H-indeno[1,2-d]thiazol-2-yl)-1-(β-D-ribofuranosyl)–uracil (7e).
Compound 7e (265 mg, 77%) was obtained as a white solid. TLC (silica gel, CH
2
Cl
2 f
/MeOH, 5:1) R
1
0
9
1
.59; UV (MeOH): λmax 358 nm (12000); H NMR (400 MHz, DMSO-d
6
) δ 12.00 (br s, 1H),
.13 (s, 1H), 7.45 (d, J = 8.3 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 6.83 (dd, J = 8.3 Hz, 2.5 Hz,
H), 5.93 (d, J = 4.7 Hz, 1H), 5.52 (br s, 1H), 5.31 (t, J = 4.3 Hz, 1H), 5.17 (br s, 1H), 4.22 (t, J
=
3 2
4.8 Hz, 1H), 4.09 (t, J = 4.8 Hz, 1H), 4.01 – 3.95 (m, 1H), 3.90 – 3.75 (m, 6H, CH , CH ),
.72 – 3.65 (m, 1H); 13C{ H} NMR (100 MHz, DMSO-d
1
) δ 162.1, 161.3, 159.8, 158.8, 149.6,
3
1
3
5
6
39.0, 138.3, 138.2, 137.78, 125.7, 110.837, 108.2, 104.7, 88.8, 84.9, 74.2, 69.7, 60.5, 55.3,
+
1.4; HR-ESI MS (m/z): [M + H] calcd for C20
H
20
N
3
O
7
S 446.1016, found 446.1032.
-(5,6-Dimethoxy-8H-indeno[1,2-d]thiazol-2-yl)-1-(β-D-ribofuranosyl)-uracil (7f).
Compound 7f (240 mg, 65%) was obtained as a bright yellow solid. TLC (silica gel,
1
CH
2
Cl
2
/MeOH, 5:1) R
f
0.54; UV (MeOH): λmax 371 nm (21200); H NMR (400 MHz, DMSO-
d
6
) δ 11.99 (br s, 1H), 9.08 (s, 1H), 7.34 (s, 1H), 7.25 (s, 1H), 5.92 (d, J = 4.9 Hz, 1H), 5.51 (d,
J = 5.4 Hz, 1H), 5.29 (t, J = 4.4 Hz, 1H), 5.16 (d, J = 5.3 Hz, 1H), 4.22 (dd, J = 10.1 Hz, 5.0 Hz,
1
H), 4.09 (dd, J = 9.8 Hz, 4.9 Hz, 1H), 4.00 – 4.95 (m, 1H), 3.86 (s, 3H), 3.84 (s, 2H), 3.81 (s,
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