2-Acylimino-3-aryl-thiazoline
2459
2-[5-(3-Nitrophenyl)-2-furoylimino]-3-phenyl-4-methyl-1,3-thiazoline 4i:
Mp 235–236 8C. IR (KBr): 3106, 1611, 1512, 1476, 1344, 1272,
1
1221 cm21. H NMR (CDCl3): d ¼ 8.45 (d, 2H, J ¼ 2.0 Hz, ArH), 8.09–
8.06 (m, 1H, ArH), 8.00–7.98 (m, 1H, ArH), 7.62–7.48 (m, 6H, ArH),
6.94–6.93 (m, 1H, FuH), 6.76–6.75 (m, 1H, FuH), 6.40 (s, 1H, C55CH),
2.07 (d, 3H, J ¼ 0.8 Hz, CH3). 13C NMR (CDCl3): d ¼ 169.6, 165.5, 153.1,
151.9, 148.6, 136.9, 134.5, 131.7, 129.9, 129.6, 129.5, 129.4, 127.9, 122.3,
119.1, 117.3, 108.8, 104.8, 15.0. Anal. calcd. for C21H15N3O4S: C, 62.21;
H, 3.73; N, 10.36. Found: C, 62.29; H, 3.70; N, 10.41.
2-[5-(3-Nitrophenyl)-2-furoylimino]-3-(4-chlorophenyl)-4-methyl-1,3-
thia-zoline 4j: Mp 217–218 8C. IR (KBr): 3106, 1620, 1533, 1461, 1353,
1
1260 cm21. H NMR (CDCl3): d ¼ 8.46 (s, 1H, ArH), 8.10–8.00 (m, 2H,
ArH), 7.55–7.38 (m, 4H, ArH), 7.30–7.24 (m, 1H, ArH), 6.92–6.88
(m, 1H, FuH), 6.77–6.74 (m, 1H, FuH), 6.40 (d, 1H, J ¼ 0.8 Hz, C55CH),
2.07 (d, 3H, J ¼ 0.8 Hz, CH3). 13C NMR (CDCl3): d ¼ 169.3, 165.6, 153.1,
151.8, 148.6, 136.9, 136.7, 134.5, 131.7, 131.4, 129.6, 129.5, 129.4, 127.9,
127.4, 122.3, 119.3, 117.3, 109.1, 104.9, 15.0. Anal. calcd. for
C21H14ClN3O4S: C, 57.34; H, 3.21; N, 9.55. Found: C, 57.40; H, 3.16; N,
10.01.
2-[5-(3-Nitrophenyl)-2-furoylimino]-3-phenyl-4-phenyl-1,3-thiazoline 4 k:
The previous described method for the reaction of 2-benzofuroyl chloride
(1b) with ammonium thiocyanate (1.5 mmol), aniline (1.0 mmol), and
phenacyl bromide (1.0 mmol) was used to prepare the product. It was
purified by recrystallization from DMF-EtOH. Mp 194–195 8C. IR (KBr):
1
3088, 1599, 1521, 1452, 1344 cm21. H NMR (CDCl3): d ¼8.53 (d, 1H,
J ¼ 2.0 Hz, ArH), 8.13–8.05 (m, 2H, ArH), 7.57–7.53 (m, 1H, ArH),
7.33–7.24 (m, 10H, ArH), 7.07 (d, 1H, J ¼ 3.6 Hz, FuH), 6.80 (d, 1H,
J ¼ 3.2 Hz, FuH), 6.70 (d, 1H, J ¼ 2.0 Hz, C55CH). 13C NMR (CDCl3):
d ¼169.6, 165.6, 153.2, 151.9, 148.6, 137.4, 136.8, 134.6, 131.7, 130.1,
129.8, 129.6, 129.5, 128.8, 128.6, 128.3, 128.1, 122.4, 119.0, 117.4, 108.8,
107.6. Anal. calcd. for C26H17N3O4S: C, 66.80; H, 3.67; N, 8.99. Found: C,
66.72; H, 3.73; N, 8.93.
2-[5-(3-Nitrophenyl)-2-furoylimino]-3-(4-chlorophenyl)-4-phenyl-1,3-thi-
azoline 4l: Mp 236–2378C. IR (KBr): 3100, 1584, 1521, 1461, 1338 cm21. 1H
NMR (CDCl3): d ¼ 8.53 (d, 1H, J ¼ 2.0 Hz, ArH), 8.16–8.07 (m, 2H, ArH),
7.59–7.54 (m, 1H, ArH), 7.32–7.19 (m, 9H, ArH), 6.95 (d, 1H, J ¼ 3.6 Hz,
FuH), 6.81 (d, 1H, J ¼ 3.2 Hz, FuH), 6.72 (d, 1H, J ¼ 2.0 Hz, C55CH). 13C
NMR (CDCl3): d ¼169.4, 165.7, 153.3, 152.0, 148.5, 139.2, 138.8, 134.9,
131.5, 130.4, 129.7, 129.4, 128.7, 128.5, 128.2, 122.5, 120.2, 117.8, 109.2,
108.1. Anal. calcd. for C26H16ClN3O4S: C, 62.21; H, 3.21; N, 8.37. Found:
C, 62.14; H, 3.19; N, 8.34.