1940
S. Murru et al. / Tetrahedron 64 (2008) 1931e1942
HRMS (ESI): MHþ, found 357.4563, C22H16N2OS requires
357.4557.
128.7, 128.8, 129.2, 129.4, 129.7, 130.3, 132.8, 138.0, 152.2,
159.4. nmax (KBr): 3021, 2854, 1618, 1577, 1489, 1352, 1141,
760, 688 cmꢁ1. C22H18N2S (342.47): calcd C 77.16, H 5.30, N
8.18, S 9.36; found C 77.23, H 5.26, N 8.31, S 9.24.
4.6.11. 2-Benzoylimino-4,5-dimethyl-3-phenyl-3H-thiazole
(1c)
White solid, Rf (25% EtOAc/hexane) 0.46, mp 128e130 ꢀC.
dH (400 MHz, CDCl3): 1.95 (s, 3H), 2.28 (s, 3H), 7.31 (m, 5H),
7.54 (m, 3H), 8.01 (d, 2H, J¼7.2 Hz). dC (100 MHz, CDCl3):
12.1, 12.4, 115.0, 128.0, 128.2, 128.3, 129.0, 129.4, 129.6,
131.4, 137.1, 138.2, 168.4, 174.1. nmax (KBr): 3054, 2923,
1596, 1558, 1481, 1349, 905, 713 cmꢁ1. C18H16N2OS
(308.41): calcd C 70.10, H 5.23, N 9.08, S 10.40; found C
70.37, H 5.31, N 9.23, S 10.26.
4.6.16. 10a,12a-Dimethyl-8-phenylimino-7-phenyl-
l,2,3,3a,3b,4,5,5a,6,7,8,10,10a,10b,11,12,12a-
hexadecahydro-1H-9-thia-7-aza-dicyclopenta[a,h]-
phenanthren-1-ol (7f)
White amorphous solid, Rf (25% EtOAc/hexane) 0.25, mp
95e98 ꢀC. dH (400 MHz, CDCl3): 0.73 (s, 3H), 0.86 (s, 3H),
0.82e2.30 (m, 20H), 3.60 (t, 1H, J¼8.8 Hz), 4.18 (m, 1H),
7.03 (m, 2H), 7.37 (m, 8H). dC (100 MHz, CDCl3): 11.2,
12.0, 20.9, 23.5, 28.5, 28.9, 30.5, 31.2, 35.7, 36.7, 37.0,
38.2, 41.8, 42.9, 50.9, 53.8, 81.9, 106.3, 121.9, 123.2, 125.2,
126.8, 128.3, 128.8, 129.4, 129.5, 137.5, 152.2, 160.8. nmax
(KBr): 3133, 2928, 2886, 1609, 1577, 1378, 1149, 764,
695 cmꢁ1. m/z: 499 (Mþ1). C32H38 N2OS (498.74): calcd
C 77.07, H 7.68, N 5.62, S 6.43; found C 76.84, H 7.71, N
5.57, S 6.50.
4.6.12. 2-Benzoylimino-3,5-diphenyl-4-methyl-3H-thiazole
(1d)
White crystalline solid, Rf (25% EtOAc/hexane) 0.70, mp
168e170 ꢀC. dH (400 MHz, CDCl3): 2.11 (s, 3H), 7.41 (m,
13H), 8.03 (d, 2H, J¼6.8 Hz). dC (100 MHz, CDCl3): 13.7,
120.5, 128.0, 128.2, 128.3, 129.1, 129.2, 129.3, 129.4, 129.6,
131.5, 132.0, 136.9, 137.9, 168.7, 174.5. nmax (KBr): 3054,
2857, 1596, 1462, 1338, 1174, 902, 718, 691 cmꢁ1. C23H18
N2OS (370.48): calcd C 74.57, H 4.90, N 7.56, S 8.65; found
C 74.73, H 5.08, N 7.38, S 8.83.
4.6.17. 2-Benzoylimino-4,5-dihydro-1H-naphtho[1,2-d]-3-
(p-tolyl)-thiazole (3g)
White cubes, Rf (25% EtOAc/hexane) 0.62, mp 196e197 ꢀC.
dH (400 MHz, CDCl3): 2.49 (s, 3H), 2.81 (t, 2H, J¼7.2 Hz), 3.03
(t, 2H, J¼7.2 Hz), 6.35 (d, 1H, J¼8 Hz), 6.88 (t, 1H, J¼7.2 Hz),
7.09 (t, 1H, J¼7.2 Hz), 7.23 (t, 2H, J¼6.8 Hz), 7.36 (m, 6H),
8.11 (d, 2H, J¼7.2 Hz). dC (100 MHz, CDCl3): 21.6, 23.0,
30.0, 122.3, 123.2, 126.5, 126.6, 127.5, 128.0, 128.1, 128.5,
129.5, 130.0, 131.3, 131.5, 136.3, 136.4, 137.1, 139.0, 169.0,
174.5. nmax (KBr): 3025, 3002, 2927, 2837, 1651, 1597, 1563,
1470, 1340, 1316, 1163, 905, 758, 714 cmꢁ1. C25H20N2OS
(396.51): calcd C 75.73, H 5.08, N 7.06, S 8.09; found C
75.79, H 5.18, N 7.18, S 8.23.
4.6.13. N-(1-Hydroxy-10a,12a-dimethyl-7-phenyl-
1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-
hexadecahydro-9-thia-7-aza-dicyclopenta[a,h]-
phenanthren-8-ylidene)-benzamide (1f)
Dark red gummy liquid, Rf (25% EtOAc/hexane) 0.21. dH
(400 MHz, CDCl3): 0.76 (s, 3H), 0.86 (s, 3H), 0.80e2.00 (m,
19H), 2.31 (d, 1H, J¼8 Hz), 2.60 (d, 1H, J¼16 Hz), 3.65 (t,
1H, J¼8.4 Hz), 4.15 (m, 1H), 7.42 (m, 7H), 7.81 (d, 1H,
J¼7.2 Hz), 8.03 (d, 2H, J¼7.2 Hz). dC (100 MHz, CDCl3):
11.2, 12.0, 21.0, 23.5, 28.5, 30.5, 31.2, 34.1, 35.7, 36.5, 36.7,
37.0, 37.8, 42.0, 43.0, 51.0, 53.8, 81.9, 117.2, 127.6, 128.0,
128.7, 129.1, 129.3, 129.4, 130.1, 131.3, 132.1, 137.2, 137.3,
168.6, 169.7, 174.2. nmax (KBr): 3131, 2923, 2878, 1654,
1608, 1580, 1376, 1243, 1149, 764, 695 cmꢁ1. C33H38 N2O2S
(526.75): calcd C 75.25, H 7.27, N 5.32, S 6.09; found C
75.41, H 7.36, N 5.26, S 6.18.
4.6.18. 2-Benzoylimino-4,5-dihydro-7-methoxy-1H-
naphtho[1,2-d]-3-(p-tolyl)-thiazole (3h)
White crystalline solid, Rf (25% EtOAc/hexane) 0.53, mp
197e199 ꢀC. dH (400 MHz, CDCl3): 2.50 (s, 3H), 2.80 (t, 2H,
J¼6.8 Hz), 3.02 (t, 2H, J¼6.8 Hz), 3.74 (s, 3H), 6.25 (d, 1H,
J¼8.8 Hz), 6.41 (d, 1H, J¼8.8 Hz), 6.79 (s, 1H), 7.34 (m, 7H),
8.09 (d, 2H, J¼8.8 Hz). dC (100 MHz, CDCl3): 21.6, 22.9,
30.2, 55.4, 111, 114.9, 124.6, 127.8, 128.1, 129.4, 129.7,
130.0, 131.5, 136.4, 137.1, 138.6, 139.0, 159.9, 168.9, 174.4.
nmax (KBr): 3021, 2924, 2841, 1649, 1602, 1563, 1468, 1339,
1318, 1268, 1165, 905, 756, 694 cmꢁ1. C26H22 N2O2S
(426.54): calcd C 73.21, H 5.20, N 6.57, S 7.52; found C
73.14, H 5.09, N 7.58, S 7.67.
4.6.14. 3,4-Diphenyl-2-phenylimino-3H-thiazole (7b)
White needles, Rf (25% EtOAc/hexane) 0.69, mp 189e
192 ꢀC. dH (400 MHz, CDCl3): 5.94 (s, 1H), 6.95e7.40 (m,
15H). dC (100 MHz, CDCl3): 97.4, 121.8, 123.4, 127.7, 128.3,
128.4, 128.5, 129.0, 129.1, 129.6, 131.8, 138.1, 140.1, 152.1,
160.4. nmax (KBr): 3049, 2923, 1618, 1577, 1486, 1360, 1138,
710, 694 cmꢁ1. C21H16 N2S (328.44): calcd C 76.80, H 4.91,
N 8.53, S 9.76; found C 76.68, H 5.04, N 8.62, S 9.58.
4.6.19. 5,50-Bis-[2-benzoylimino-4-methyl-3-(p-tolyl)-3H-
thiazole] (3i)
4.6.15. 4-Methyl-3,5-diphenyl-2-phenylimino-3H-thiazole
(7d)
White crystalline solid, Rf (25% EtOAc/hexane) 0.74, mp
177e179 ꢀC. dH (400 MHz, CDCl3): 1.93 (s, 3H), 7.01 (m,
2H), 7.26 (m, 3H), 7.33 (m, 3H), 7.43 (m, 2H), 7.54 (m, 2H).
dC (100 MHz, CDCl3): 14.2, 109.6, 121.8, 123.2, 127.3,
White amorphous solid, Rf (25% EtOAc/hexane) 0.65, mp
335e338 ꢀC. dH (400 MHz, CDCl3): 2.13 (s, 6H), 2.51 (s,
6H), 7.30 (m, 8H), 7.41 (m, 6H), 8.05 (d, 4H, J¼8 Hz). dC
(100 MHz, CDCl3): 14.1, 21.6, 109.5, 127.9, 128.1, 129.6,
130.5, 131.8, 134.6, 135.1, 136.7, 139.7, 169.1, 174.9. nmax
(KBr): 3063, 2909, 1602, 1572, 1475, 1242, 818 cmꢁ1. m/z: