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A. Alizadeh et al. / Tetrahedron 67 (2011) 1709e1715
(KBr) (nmax, cmꢀ1): 3205 (OH), 1641 (C]O), 1620 (C]C), 1554 and
1442 (Ar), 1048 (C]S). Anal. Calcd for C24H18ClNO2S2 (451.98): C,
63.78; H, 4.01; N, 3.10%. Found: C, 63.81; H, 4.03; N, 3.13%. MS (EI,
70 eV): m/z (%)¼451 (Mþ, 5), 430 (9), 416 (17), 400 (37), 310 (18),
268 (7),163 (18),125 (44),105 (100), 89 (6), 77 (91), 51 (19). 1H NMR
(500.13 MHz, CDCl3): dH¼3.61e4.42 (1H, br, OH), 4.84 (1H, d,
2JHH¼16.2 Hz, CH2N), 5.31 (1H, d, 2JHH¼16.2 Hz, CH2N), 7.06 (1H, s,
7.13e7.23 (4H, m, 4CH of Ar), 7.32e7.39 (4H, m, 4CH of Ar),
3
7.43e7.49 (3H, m, 3CH of Ar), 7.52 (2H, t, JHH¼7.4 Hz, 2CH of Ar),
7.77 (2H, d, 3JHH¼8.1 Hz, 2CH of Ar). 13C NMR (125.75 MHz, CDCl3):
dC¼17.0 (CHCH3), 57.0 (CHCH3), 103.2 (COH), 113.0 (C]CH), 125.6
(2CH of Ar), 127.9 (2CH of Ar), 128.2 (2CH of Ar), 128.3 (2CH of Ar),
128.7 (2CH of Ar), 128.7 (2CH of Ar), 128.8 (CH of Ar), 133.2 (CH of
Ar), 136.9 (CipsoeCOH), 138.7 (CipsoeCHN), 138.9 (CipsoeCO), 162.4
(C]CH), 188.5 (CO), 192.0 (CS).
3
C]CH), 7.10 (2H, d, JHH¼7.9 Hz, 2CH of Ar), 7.18 (1H, t,
3
3JHH¼6.30 Hz, CH of Ar), 7.28 (2H, t, JHH¼6.7 Hz, 2CH of Ar), 7.30
(2H, d, 3JHH¼6.5 Hz, 2CH of Ar), 7.32 (2H, d, 3JHH¼7.8 Hz, 2CH of Ar),
4.2.6. 2-(4-Hydroxy-3-methyl-4-phenyl-2-thioxo-1,3-thiazolan-5-
yliden)-1-phenyl-1-ethanone (5f). Yellow oil, 0.22 g, yield: 66%. Rf
(12% EtOAc/n-hexane): 0.22; IR (KBr) (nmax, cmꢀ1): 3240 (OH),
1677 (C]O), 1596 (C]C), 1555 and 1447 (Ar), 1055 (C]S). Anal.
Calcd for C18H15NO2S2 (341.44): C, 63.32; H, 4.43; N, 4.10%.
Found: C, 63.36; H, 4.42; N, 4.13%. MS (EI, 70 eV): m/z (%)¼341
(Mþ, 43), 325 (7), 268 (26), 220 (6), 163 (100), 135 (10), 105 (93),
85 (28), 77 (81), 72 (66), 51 (26). 1H NMR (500.13 MHz, CDCl3):
dH¼3.09 (3H, s, NMe), 5.31e5.80 (1H, br, OH), 7.08 (1H, s, C]CH),
7.28 (2H, t, 3JHH¼7.5 Hz, 2CH of Ar), 7.34 (1H, t, 3JHH¼7.2 Hz, CH of
3
3
7.41 (1H, t, JHH¼7.3 Hz, CH of Ar), 7.50 (2H, t, JHH¼6.9 Hz, 2CH of
Ar), 7.76 (2H, d, JHH¼7.4 Hz, 2CH of Ar). 13C NMR (125.7 MHz,
3
CDCl3): dC¼45.8 (CH2N), 101.9 (COH), 113.9 (C]CH), 125.5 (2CH of
Ar), 126.5 (2CH of Ar), 128.3 (2CH of Ar), 128.4 (2CH of Ar), 128.7
(2CH of Ar), 128.8 (2CH of Ar), 128.8 (CH of Ar), 129.2 (CH of Ar),
132.5 (CipsoeCl), 136.5 (CipsoeCOH), 136.5 (CipsoeCH2N), 138.3
(CipsoeCO), 161.3 (C]CH), 188.7 (CO), 194.1 (CS).
4.2.3. 2-[4-Hydroxy-3-(4-methoxybenzyl)-4-phenyl-2-thioxo-1,3-
thiazolan-5-yliden]-1-phenyl-1-ethanone (5c). Pale yellow powder,
mp 179e181 ꢁC, 0.10 g, yield: 22%. Rf (12% EtOAc/n-hexane): 0.28; IR
(KBr) (nmax, cmꢀ1): 3265 (OH), 1638 (C]O), 1610 (C]C), 1551 and
1459 (Ar), 1043 (C]S). Anal. Calcd for C25H21NO3S2 (447.56): C,
67.09; H, 4.73; N, 3.13%. Found: C, 67.14; H, 4.75; N, 3.14%. MS (EI,
70 eV): m/z (%)¼355 (15), 307 (9), 264 (27), 250 (34), 183 (43), 167
(18), 146 (39), 105 (100), 91 (56), 77 (77), 57 (60), 43 (57). 1H NMR
(500.13 MHz, CDCl3): dH¼2.48e2.60 (1H, br, OH), 3.76 (3H, s, OMe),
4.38 (1H, d, 2JHH¼14.7 Hz, CH2N), 5.28 (1H, d, 2JHH¼14.7 Hz, CH2N),
6.73 (2H, d, 3JHH¼8.7 Hz, 2CH of Ar), 7.08 (1H, s, C]CH), 7.29 (1H, t,
3JHH¼7.1 Hz, 1CH of Ar), 7.36e7.39 (5H, m, 5CH of Ar), 7.40e7.42
(1H, m, CH of Ar), 7.46 (1H, t, 3JHH¼7.4 Hz, CH of Ar), 7.50e7.52 (2H,
3
3
Ar), 7.38 (1H, t, JHH¼7.4 Hz, CH of Ar), 7.41 (2H, t, JHH¼7.6 Hz,
3
2CH of Ar), 7.49 (2H, d, JHH¼7.6 Hz, 2CH of Ar), 7.74 (2H, d,
3JHH¼7.8 Hz, 2CH of Ar). 13C NMR (125.7 MHz, CDCl3): dC¼31.9
(NCH3), 101.5 (COH), 113.9 (C]CH), 128.3 (2CH of Ar), 128.5 (2CH
of Ar), 129.0 (2CH of Ar), 129.7 (2CH of Ar), 130.9 (CH of Ar), 133.4
(CH of Ar), 136.5 (CipsoeOH), 138.7 (CipsoeCO), 161.4 (C]CH), 188.7
(CO), 192.5 (CS).
4.2.7. 2-((4-Hydroxy)-4-phenyl-3-propyl-2-thioxo-1,3-thiazolan-5-
yliden)-1-phenyl-1-ethanone (5g). Yellow powder, mp 198e200 ꢁC,
0.05 g, yield: 13%. Rf (12% EtOAc/n-hexane): 0.35; IR (KBr) (nmax
,
cmꢀ1): 3250 (OH), 1640 (C]O), 1595 (C]C), 1552 and 1447 (Ar),
1048 (C]S). Anal. Calcd for C20H19NO2S2 (369.49): C, 65.01; H, 5.18;
N, 3.79%. Found: C, 65.04; H, 5.20; N, 3.82%. MS (EI, 70 eV): m/z (%)¼
369 (Mþ, 14), 355 (10), 269 (19), 264 (16), 211 (11), 163 (37), 105
(100), 91 (10), 85 (18), 77 (79), 58 (24), 43 (65), 41 (16). 1H NMR
3
m, 2CH of Ar), 7.82 (2H, t, JHH¼7.3 Hz, 2CH of Ar). 13C NMR
(125.75 MHz, CDCl3): dC¼48.2 (CH2N), 55.3 (OMe), 102.0 (COH),
113.4 (C]CH), 125.3 (2CH of Ar), 128.3 (2CH of Ar), 128.7 (2CH of
Ar), 128.9 (2CH of Ar), 129.0 (2CH of Ar),129.6 (2CH of Ar), 130.3 (CH
of Ar), 133.3 (CH of Ar), 134.1 (CipsoeCH2N), 136.5 (CipsoeCOH), 138.9
(CipsoeCO), 154.9 (CipsoeOMe), 161.1 (C]CH), 181.3 (CO), 188.2 (CS).
3
(500.13 MHz, CDCl3): dH¼0.79 (3H, t, JHH¼7.4 Hz, NCH2CH2CH3),
1.37e1.41 (1H, m, NCH2CH2CH3), 1.64e1.68 (1H, m, NCH2CH2CH3),
3.28e3.33 (1H, m, NCH2CH2CH3), 3.70e3.76 (1H, m, NCH2CH2CH3),
4.19 (1H, br, OH), 7.04 (1H, s, C]CH), 7.35 (2H, t, 3JHH¼7.4 Hz, 2CH of
4.2.4. 2-(3-Benzyl-4-hydroxy-4-phenyl-2-thioxo-1,3-thiazolan-5-yli-
den)-1-phenyl-1-ethanone(5d). Pale yellow powder, mp 195e197 ꢁC,
3
Ar), 7.39e7.44 (4H, m, 4CH of Ar), 7.52 (2H, d, JHH¼8.1 Hz, 2CH of
3
0.11 g, yield: 25%. Rf (12% EtOAc/n-hexane): 0.27; IR (KBr) (nmax
,
Ar), 7.78 (2H, d, JHH¼7.5 Hz, 2CH of Ar). 13C NMR (125.75 MHz,
cmꢀ1): 3225 (OH), 1640 (C]O), 1596 (C]C), 1555 and 1447 (Ar),
1050 (C]S). Anal. Calcd for C24H19NO2S2 (417.54): C, 69.04; H, 4.59;
N, 3.35%. Found: C, 69.03; H, 4.60; N, 3.33%. MS (EI, 70 eV): m/z (%)¼
417 (Mþ, 8), 401 (5), 312 (10), 269 (31), 223 (12), 163 (84), 149 (37),
105 (91), 91 (100), 77 (68), 65 (19), 51 (22). 1H NMR (500.13 MHz,
CDCl3): dC¼10.98 (NCH2CH2CH3), 20.4 (NCH2CH2CH3), 47.5
(NCH2CH2CH3), 101.4 (COH), 113.1 (C]CH), 125.4 (2CH of Ar), 128.4
(2CH of Ar), 128.6 (CH of Ar), 128.9 (2CH of Ar), 129.6 (CH of Ar),
133.3 (2CH of Ar), 133.7 (CipsoeOH), 134.8 (CH of Ar), 138.3
(CipsoeCO), 162.1 (C]CH), 189.2 (CO), 191.9 (CS).
2
CDCl3): dH¼4.21e4.33 (1H, br, OH), 4.67 (1H, d, JHH¼15 Hz, CH2N),
5.20 (1H, d, 2JHH¼15 Hz, CH2N), 7.01 (1H, s, C]CH), 7.12e7.17 (3H, m,
3CH of Ar), 7.23e7.32 (7H, m, 7CH of Ar), 7.37 (1H, t, 3JHH¼7.0 Hz, CH
of Ar), 7.45e7.49 (2H, m, 2CH of Ar), 7.72 (2H, d, 3JHH¼7.4 Hz, 2CH of
Ar). 13C NMR (125.7 MHz, CDCl3): dC¼48.8 (CH2N), 102.1 (COH), 113.5
(C]CH), 125.5 (2CH of Ar), 127.0 (2CH of Ar), 128.1 (2CH of Ar), 128.3
(2CH of Ar), 128.5 (2CH of Ar), 128.7 (2CH of Ar), 129.0 (CH of Ar),
129.5 (CH of Ar), 133.3 (CH of Ar), 136. 5 (CipsoeCOH), 136.5 (Cipsoe
CH2N), 138.7 (CipsoeCO), 161.5 (C]CH), 188.6 (CO), 193.9 (CS).
4.2.8. 2-(4-Hydroxy-3-isobutyl-4-phenyl-2-thioxo-1,3-thiazolan-5-
yliden)-1-phenyl-1-ethanone (5h). Orange powder, mp 141e143 ꢁC,
0.14 g, yield: 38%. Rf (12% EtOAc/n-hexane): 0.37; IR (KBr) (nmax
,
cmꢀ1): 3285 (OH), 1623 (C]O), 1595 (C]C), 1540 and 1446 (Ar),
1051 (C]S).Anal. Calcd for C21H21NO2S2 (383.52): C, 65.77; H,
5.52; N, 3.65%. Found: C, 65.83; H, 5.55; N, 3.66%. MS (EI, 70 eV):
m/z (%)¼327 (4), 300 (12), 290 (16), 268 (35), 262 (9), 163 (41), 146
(17), 115 (20), 105 (100), 91 (38), 77 (95), 57 (28), 43 (37), 41 (39).
1H NMR (500.1 MHz, CDCl3): dH¼0.81 (3H, d, 3JHH¼6.7 Hz, NCH2CH
3
4.2.5. 2-[4-Hydroxy-4-phenyl-3-(1-phenylethyl)-2-thioxo-1,3-thia-
zolan-5-yliden]-1-phenyl-1-ethanone (5e). Pale yellow powder, mp
163e165 ꢁC, 0.03 g, yield: 7%. Rf (12% EtOAc/n-hexane): 0.30; IR
(KBr) (nmax, cmꢀ1): 3220 (OH), 1636 (C]O), 1594 (C]C), 1529 and
1443 (Ar), 1056 (C]S). Anal. Calcd for C25H21NO2S2 (431.56): C,
69.58; H, 4.90; N, 3.25%. Found: C, 69.60; H, 4.95; N, 3.27%. MS (EI,
70 eV): m/z (%)¼422 (6), 322 (10), 268 (43), 236 (29), 167 (17), 149
(51), 105 (100), 91 (38), 77 (71), 57 (44), 43 (41). 1H NMR
(500.13 MHz, CDCl3): dH¼1.74 (3H, d, 3JHH¼7.2 Hz, CHCH3), 4.61 (1H,
(CH3)2), 0.88 (3H, d, JHH¼6.9 Hz, NCH2CH(CH3)2), 2.09e2.16 (1H,
2
3
m, NCH2CH(CH3)2), 3.13 (1H, dd, JHH¼13.7 Hz, JHH¼8.0 Hz,
2
3
NCH2CH2CH3), 3.79 (1H, dd, JHH¼13.7 Hz, JHH¼6.8 Hz,
NCH2CH2CH3), 3.80e3.98 (1H, br, OH), 7.04 (1H, s, C]CH), 7.31
(2H, t, 3JHH¼7.4 Hz, 2CH of Ar), 7.37e7.41 (4H, m, 4CH of Ar), 7.52
(2H, d, 3JHH¼7.5 Hz, 2CH of Ar), 7.76 (2H, d, 3JHH¼7.2 Hz, 2CH of Ar).
13C NMR (125.75 MHz, CDCl3): dC¼20.6 (NCH2CH(CH3)2), 20.8
(NCH2CH(CH3)2), 27.5 (NCH2CH(CH3)2), 53.5 (NCH2CH(CH3)2),
102.2 (COH), 113.3 (C]CH), 125.3 (2CH of Ar), 128.3 (2CH of Ar),
128.6 (2CH of Ar), 129.0 (2CH of Ar), 129.5 (CH of Ar), 133.2 (CH of
3
br, OH), 5.39 (1H, q, JHH¼7.2 Hz, CHCH3), 6.96 (1H, s, C]CH),