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tion with 3,5-di-tert-butyl-4-hydroxybenzyl alcohol. Flash
column chromatography: eluent cyclohexane/ethyl acetate
(6:4, v/v).Yield 38%; m.p. 153–155 °C (trituration with petrol
ether 40–60 °C). 1H NMR (d6-DMSO) d 7.97 (dd, 1H, J = 1.4,
7.9 Hz, H-5), 7.85 (ddd, 1H, J = 1.4, 7.3, 8.1 Hz, H-7), 7.69
(dd, 1H, J = 1.0, 8.1 Hz, H-8), 7.52 (ddd, 1H, J = 1.0, 7.9,
8.1 Hz, H-6), 7.29 (m, 5H, aromatic), 6.99 (s*, 1H, OH), 6.69
(s, 2H, aromatic), 4.94 (s, 2H, NCH2Ph), 4.59 (s, 2H,
NCH2Ph), 1.23 (s, 18H, tert-butyl). IR(Nujol) 3563, 1679,
1603, 1326, 1177, 1052 cm−1. Anal. (C29H34N2O4S): C, H,
N.
1H, OH), 6.74 (s, 2H, aromatic), 5.01 (s, 2H, NCH2Ph), 4.69
(s, 2H, NCH2Ph), 1.23 (s, 18H, tert-butyl). IR(Nujol) 3600,
1677, 1596, 1292, 1186 cm−1. Anal. (C29H33Cl2N2O4S): C,
H, N.
4.1.12. 3-(4-Chlorobenzyl)-1-(3,5-di-tert-butyl-4-hydroxy-
benzyl)-6,7-dimethoxy-1H-2,1,3-benzothiadiazin-4(3H)-one
2,2-dioxide (14)
This compound was obtained starting from 3-(4-
chlorobenzyl)-6,7-dimethoxy-1H-2,1,3-benzothiadiazin-
4(3H)-one 2,2-dioxide (43) by reaction with 3,5-di-tert-butyl-
4-hydroxybenzyl alcohol. Flash column chromatography:
eluent cyclohexane/ethyl acetate (6:4, v/v). Yield 25%; m.p.
151–152 °C (DMF/water). 1H NMR (d6-DMSO) d 7.40 (bd,
2H, J = 8.5 Hz, 4-chlorobenzyl H-3 and H-5), 7.35 (s, 1H,
H-5), 7.27 (bd, 2H, J = 8.5 Hz, 4-chlorobenzyl H-2 and H-6),
7.12 (s, 1H, H-8), 7.02 (s*, 1H, OH), 6.73 (s, 2H, aromatic),
4.89 (s, 2H, NCH2Ph), 4.62 (s, 2H, NCH2Ph), 3.89 (s, 3H,
OCH3), 3.23 (s, 3H, OCH3), 1.27 (s, 18H, tert-butyl). IR(Nu-
jol) 3565, 1666, 1609, 1281, 1176 cm−1. Anal.
(C31H37ClN2O6S): C, H, N.
4.1.9. 3-Benzyl-1-(3,5-di-tert-butyl-4-hydroxybenzyl)-6,7-
dimethoxy-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-
dioxide (8)
This compound was obtained starting from 3-benzyl-6,7-
dimethoxy-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide
(37) by reaction with 3,5-di-tert-butyl-4-hydroxybenzyl alco-
hol. Flash column chromatography: eluent cyclohexane/ethyl
acetate (6:4, v/v). Yield 57%; m.p. 140–142 °C (methanol/
1
water). H NMR (d6-DMSO) d 7.33 (s, 1H, H-5), 7.30 (m,
5H, aromatic), 7.10 (s, 1H, H-8), 6.98 (s*, 1H, OH), 6.70 (s,
2H, aromatic), 4.85 (s, 2H, NCH2Ph), 4.58 (s, 2H, NCH2Ph),
3.86 (s, 3H, OCH3), 3.80 (s, 3H, OCH3), 1.24 (s, 18H, tert-
butyl). IR(Nujol) 3621, 1678, 1603, 1259, 1175, 1007 cm−1.
Anal. (C31H38N2O6S): C, H, N.
4.1.13. 1-(3,5-Di-tert-butylbenzyl)-3-isopropyl-1H-2,1,3-
benzothiadiazin-4(3H)-one 2,2-dioxide (15)
This compound was obtained starting from 3-isopropyl-
1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide (33) by
reaction with 3,5-di-tert-butylbenzyl alcohol. Flash column
chromatography: eluent cyclohexane/ethyl acetate (8.5:1.5,
v/v). Yield 68%; m.p. 75–77 °C (DMF/water). 1H NMR (d6-
DMSO) d 8.02 (dd, 1H, J = 1.6, 7.8 Hz, H-5), 7.79 (ddd, 1H,
J = 1.6, 7.5, 8.2 Hz, H-7), 7.62 (dd, 1H, J = 1.1, 8.2 Hz, H-8),
7.47 (ddd, 1H, J = 1.1, 7.5, 7.8 Hz, H-6), 7.26 (t, 1H,
J = 1.7 Hz, H-4′ di-tert-butylbenzyl), 6.80 (d, 2H, J = 1.7 Hz,
H-2′ and H-6′ di-tert-butylbenzyl), 5.08 (s, 2H, NCH2Ph),
4.57 (sep, 1H, J = 6.9 Hz, NCH), 1.17 (d, 6H, J = 6.9 Hz,
CH3). 1.13 (s, 18H, tert-butyl), IR(Nujol) 1679, 1600, 1316,
1251, 1194, 1171, 1138, 1100, 1046, 977, 890, 855, 696,
610 cm−1. Anal.(C25H34N2O3S): C, H, N.
4.1.10. 3-(2-Chlorobenzyl)-1-(3,5-di-tert-butyl-4-hydroxy-
benzyl)-6,7-dimethoxy-1H-2,1,3-benzothiadiazin-4(3H)-one
2,2-dioxide (11)
This compound was obtained starting from 3-(2-
chlorobenzyl)-6,7-dimethoxy-1H-2,1,3-benzothiadiazin-
4(3H)-one 2,2-dioxide (40) by reaction with 3,5-di-tert-butyl-
4-hydroxybenzyl alcohol. Flash column chromatography:
eluent cyclohexane/ethyl acetate (8:2, v/v). Yield 42%; m.p.
157–160 °C (trituration with petrol ether 40–60 °C). 1H NMR
(d6-DMSO) d 7.49 (m, 1H, aromatic), 7.36 (s, 1H, H-5), 7.31
(m, 2H, aromatic), 7.27 (s, 1H, H-8), 7.15 (m, 1H, aromatic),
7.01 (s*, 1H, OH), 6.70 (s, 2H, aromatic), 4.91 (s, 2H,
NCH2Ph), 4.65 (s, 2H, NCH2Ph), 3.95 (s, 3H, OCH3), 3.84
(s, 3H, OCH3), 1.27 (s, 18H, tert-butyl). IR(Nujol) 3590, 1677,
1605, 1284, 1183, 1010 cm−1. Anal. (C31H37ClN2O6S): C,
H, N.
4.1.14. 1-(3-Iodobenzyl)-3-isopropyl-1H-2,1,3-benzothiadi-
azin-4(3H)-one 2,2-dioxide (16)
This compound was obtained starting from 3-isopropyl-
1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide (33) by
reaction with (3-iodophenyl)methanol. Flash column chro-
matography: eluent cyclohexane/ethyl acetate (7:3, v/v).Yield
67%; m.p. 97–100 °C. 1H NMR (d6-DMSO) d 8.00 (dd, 1H,
J = 1.6, 7.7 Hz, H-5), 7.76 (ddd, 1H, J = 1.6, 7.4, 8.0 Hz,
H-7 aromatic), 7.66–7.54 (m, 3H, aromatic), 7.44 (ddd, 1H,
J = 1.2, 7.7, 8.0 Hz, H-6 aromatic), 7.14–7.03 (m, 2H, aro-
matic), 5.10 (s, 2H, NCH2Ph), 4.80 (sep, 1H, J = 6.9 Hz,
NCH), 1.39 (d, 6H, J = 6.9 Hz, CH3). IR(Nujol) 1682, 1603,
1567, 1319, 1301, 1248, 1170, 1046, 996, 859, 793, 743 cm−1.
Anal. (C17H17IN2O3S): C, H, N.
4.1.11. 7-Chloro-3-(4-chlorobenzyl)-1-(3,5-di-tert-butyl-4-
hydroxybenzyl)-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-
dioxide (13)
This compound was obtained starting from 7-chloro-3-(4-
chlorobenzyl)-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-
dioxide (42) by reaction with 3,5-di-tert-butyl-4-hydroxy-
benzyl alcohol. Flash column chromatography: eluent
chloroform. Yield 40%; m.p. 138–142 °C (methanol/water).
1H NMR (d6-DMSO) d 7.95 (d, 1H, J = 8.5 Hz, H-5), 7.88
(d, 1H, J = 2.0 Hz, H-8), 7.56 (dd, 1H J = 2.0, 8.5 Hz, H-6),
7.38 (bd, 2H, J = 8.5 Hz, 4-chlorobenzyl H-3 and H-5), 7.27
(bd, 2H, J = 8.5 Hz, 4-chlorobenzyl H-2 and H-6), 7.02 (s*,