Journal of Sulfur Chemistry 535
4.2.4. 7-(4-Ethoxyphenyl)-5,6-bis-hydroxycarbonyl-tetrahydrothiopyrano-7H[2,3-d]thiazole-
2-thione-N-phenylimide (5d)
Pale violet crystals, yield 0.34 g (75%), mp. 235◦C; νmax/cm−1 (KBr) 3077 (NH), 1784 and 1721
(imide CO); 1H NMR (DMSO-d6) δ = 1.27 (t, 3H, J = 6.7 Hz, CH3), 4.04–4.11(dd, 1H, J = 6,
8.7 Hz, H-6), 4.23 (q, 2H, J = 6.3 Hz, CH2), 4.68 (d, 1H, J = 6 Hz, H-5), 5.30 (d, 1H, J = 9 Hz,
H-7), 6.81–7.42 (m, 9H, Ar.), 13.76 (s, 1H, NH); m/z = 454.58. Anal. Calcd. C22H18N2O3S3: C,
58.13; H, 3.99; N, 6.16; S, 21.16. Found: C, 58.41; H, 3.79; N, 6.40; S, 21.34.
4.2.5. 7-(Benzo[d][1,3]dioxo)-5,6-bis-hydroxycarbonyl-tetrahydrothiopyrano-7H[2,3-
d]thiazole-2-thione-N-phenylimide (5e)
Pale violet crystals, yield 0.37 g (82%), mp. 248◦C; νmax/cm−1 (KBr) 3086 (NH), 1780 and 1720
(imide CO); 1H NMR (DMSO-d6) 4.10–4.15 (dd, 1H, J = 6, 9 Hz, H-6), 4.78 (d, 1H, J = 6 Hz,
H-5), 5.38 (d, 1H, J = 9 Hz, H-7), 6.23 (s, 2H, CH2), 6.76–7.68 (m, 8H, Ar.), 13.84 (s, 1H, NH);
m/z = 454.54.Anal. Calcd. C21H14N2O4S3: C, 55.49; H, 3.18; N, 6.16; S, 21.16. Found: C, 55.31;
H, 3.29; N, 6.40; S, 21.34.
4.2.6. 7-(Furan-2yl)-5,6-bis-hydroxycarbonyl-tetrahydrothiopyrano-7H[2,3-d]thiazole-2-
thione-N-phenylimide (5f)
Pale brown crystals, yield 0.3 g (76%), mp. 224◦C; νmax/cm−1 (KBr) 3069 (NH), 1780 and
1
1719 (imide CO); H NMR (DMSO-d6) δ = 3.98–4.01 (dd, 1H, J = 6, 8.7 Hz, H-6), 4.71 (d,
1H, J = 5.7 Hz, H-5), 5.28 (d, 1H, J = 9.3 Hz, H-7), 6.13 (d, 1H, J = 6.6 Hz, furan), 6.34 (m,
1H, furan), 7.28–7.68 (m, 5H, Ar.), 8.11 (d, 1H, J = 6 Hz, furan), 13.81 (s, 1H, NH).13C NMR
(DMSO-d6) δ = 35.1, 37.2, 44.1, 89.5, 106.3, 113.1, 128.1, 128.8, 129.2, 133.1, 143.3, 152.2,
157.1, 172.9, 177.8, 189.4. m/z = 400.49. Anal. Calcd. C18H12N2O3S3: C, 53.98; H, 3.02; N,
6.99; S, 24.02. Found: C, 53.79; H, 3.20; N, 6.76; S, 24.20.
4.2.7. 7-(Thiophen-2-yl)-5,6-bis-hydroxycarbonyl-tetrahydrothiopyrano-7H[2,3-d]thiazole-2-
thione-N-phenylimide (5g)
Pale brown crystals, yield 0.32 g (78%), mp. 178◦C [lit. 175◦C](24); νmax/cm−1 (KBr) 3210 (NH),
1780 and 1754 (imide CO); 1H NMR (DMSO-d6) δ = 3.88–3.86 (d, 1H, J = 6, 9 Hz, H-6), 4.74
(d, 1H, J = 6 Hz, H-5), 5.18 (d, 1H, J = 9 Hz, H-7), 6.78 (d, 1H, J = 7.5 Hz, thiophene), 6.94 (m,
1H, thiophene), 7.21–7.58 (m, 6H, Ar and thiophene), 13.78 (s, 1H, NH); m/z = 416.56. Anal.
Calcd. C18H12N2O2S4: C, 51.90; H, 2.90; N, 6.72; S, 30.79. Found: C, 51.73; H, 3.08; N, 6.96;
S, 30.60.
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