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070
M.-W. Ding et al.
PAPER
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IR (KBr): 3274 (NH), 1700 (C=O), 1636 (C=C), 1585, 1260 cm–1.
C NMR (400 MHz, DMSO-d ): d = 165.4 (C = O), 159.9 (C ),
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8
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52.7 (C ), 141.6, 137.1, 133.7, 132.0, 130.5, 129.6, 128.9, 125.6,
23.9, 118.1, 114.8 (ArC), 20.5 (CH3).
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H NMR (400 MHz, DMSO-d ): d = 10.53 (s, 1 H, NH), 8.26–6.91
6
(
m, 8 H, ArH), 7.10 (s, 1 H, =CH), 2.33 (s, 3 H, CH3).
+
MS: m/z (%) = 334 (53) [M ], 306 (61), 204 (22), 131 (100).
13
C NMR (400 MHz, DMSO-d ): d = 165.7 (C=O), 159.9 (C ),
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Anal. Calcd for C H N OS: C, 64.65; H, 4.22; N, 16.75. Found:
152.5 (C ), 141.7, 139.6, 138.0, 133.4, 132.7, 130.1, 129.4, 128.9,
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14
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2
C, 64.57; H, 4.12; N, 16.86.
125.7, 123.3, 119.8, 114.0 (ArC), 21.9 (CH3).
+
MS: m/z (%) = 368 (6) [M ], 340 (11), 253 (6), 150 (100).
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g
Anal. Calcd for C H ClN OS: C, 58.62; H, 3.55; N, 15.19. Found:
Yellow crystals; mp 277–278 °C.
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4
C, 58.52; H, 3.39; N, 15.29.
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IR (KBr): 3290 (NH), 1696 (C=O), 1636 (C=C), 1588, 1116 cm .
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H NMR (400 MHz, DMSO-d ): d = 10.59 (s, 1 H, NH), 8.22–7.12
7l
6
(
m, 10 H, ArH), 7.09 (s, 1 H, =CH).
Yellow crystals; mp 242–244 °C.
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3
IR (KBr): 3265 (NH), 1694 (C=O), 1638 (C=C), 1596, 1242 cm–1.
C NMR (400 MHz, DMSO-d ): d = 165.1 (C=O), 159.8 (C ),
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52.4 (C ), 141.8, 139.2, 138.7, 133.5, 132.2, 130.2, 129.1, 128.8,
24.8, 122.6, 118.0, 115.1 (ArC).
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H NMR (400 MHz, DMSO-d ): d = 10.99 (s, 1 H, NH), 8.26–7.38
6
(
m, 9 H, ArH), 7.09 (s, 1 H, =CH).
+
MS: m/z (%) = 320 (72) [M ], 292 (77), 204 (6), 118 (100).
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C NMR (400 MHz, DMSO-d ): d = 165.8 (C=O), 159.8 (C ),
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Anal. Calcd for C H N OS: C, 63.73; H, 3.78; N, 17.49. Found:
152.8 (C ), 142.0, 139.9, 135.0, 133.6, 132.7, 130.3, 129.3, 128.7,
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C, 63.78; H, 3.71; N, 17.63.
125.8, 123.6, 118.3, 114.0 (ArC).
+
MS: m/z (%): 356 (22), 354 (63) [M ], 326 (68), 150 (46), 118
7
h
(
100).
Yellow crystals, mp 254-256 °C.
Anal. Calcd for C H ClN OS: C, 57.55; H, 3.12; N, 15.79. Found:
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IR (KBr): 3269 (NH), 1694 (C=O), 1659 (C=C), 1581, 1114 cm .
C, 57.48; H, 3.25; N, 15.98.
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H NMR (400 MHz, DMSO-d ): d = 10.73 (s, 1 H, NH), 8.22–7.35
m, 9 H, ArH), 7.10 (s, 1 H, =CH).
6
(
7m
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3
Yellow crystals; mp 235–236 °C.
C NMR (400 MHz, DMSO-d ): d = 165.4 (C=O), 159.9 (C ),
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52.6 (C ), 141.2, 139.6, 138.5, 133.7, 132.3, 130.3, 129.8, 127.8,
25.3, 123.4, 118.0, 115.2 (ArC).
IR (KBr): 3270 (NH), 1693 (C=O), 1631 (C=C), 1595, 1239 cm .
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H NMR (400 MHz, DMSO-d ): d = 10.77 (s, 1 H, NH), 8.25–7.29
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+
MS: m/z (%) = 354 (5) [M ], 326 (8), 152 (52), 116 (100).
(m, 8 H, ArH), 7.11 (s, 1 H, =CH).
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Anal. Calcd for C H ClN OS: C, 57.55; H, 3.12; N, 15.79. Found:
C, 57.41; H, 3.06; N, 15.80.
C NMR (400 MHz, DMSO-d ): d = 165.9 (C=O), 159.8 (C ),
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1
7
11
4
152.9 (C ), 142.4, 139.6, 135.4, 133.5, 132.7, 130.7, 129.5, 128.5,
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25.8, 123.8, 118.4, 114.5 (ArC).
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i
+
MS: m/z (%) = 388 (6) [M ], 360 (10), 185 (12), 153 (100).
Yellow crystals; mp 251–252 °C.
Anal. Calcd for C H Cl N OS: C, 52.46; H, 2.59; N, 14.39.
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17 10
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4
IR (KBr): 3270 (NH), 1692 (C=O), 1632 (C=C), 1593, 1117 cm .
Found: C, 52.31; H, 2.44; N, 14.57.
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H NMR (400 MHz, DMSO-d ): d = 10.73 (s, 1 H, NH), 8.22–7.43
m, 9 H, ArH), 7.10 (s, 1 H, =CH).
6
(
Acknowledgment
1
3
C NMR (400 MHz, DMSO-d ): d = 164.7 (C=O), 159.8 (C ),
52.6 (C ), 141.2, 138.9, 138.5, 133.6, 132.0, 130.4, 129.0, 128.7,
25.9, 123.7, 120.2, 114.6 (ArC).
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We gratefully acknowledge financial support of this work by the
National Natural Science Foundation of China (Project
No.20102001).
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+
MS: m/z (%) = 400 (25) [M ], 398 (24), 372 (23), 370 (23), 196 (47),
1
16 (100).
Anal. Calcd for C H BrN OS: C, 51.14; H, 2.78; N, 14.03. Found: References
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C, 51.23; H, 2.64; N, 14.07.
(
(
1) Sulkowski, T. S.; Strike, D. P.; Elockdah, H. M. US
599829, 1997; Chem. Abstr. 1997, 126, 195251h.
2) Pilkington, B. L.; Russell, S. E.; Whittle, A. J.; Mound, W.
R.; Turnbull, M. D.; Kozakiewicz, A. M.; Whittingham, W.
G. GB 2329180, 1999; Chem. Abstr. 1999, 131, 44817z.
5
7
j
Yellow crystals; mp 246–247 °C.
–
1
IR (KBr): 3291 (NH), 1697 (C=O), 1638 (C=C), 1595, 1243 cm .
1
H NMR (400 MHz, DMSO-d ): d = 10.50 (s, 1 H, NH), 8.25–7.20
m, 8 H, ArH), 7.10 (s, 1 H, =CH), 2.28 (s, 3 H, CH ).
(3) Khodair, A. I.; El-Subbagh, H. I.; Al-Obaid, A. M.
6
(
Phosphorus, Sulfur Silicon Relat. Elem. 1998, 140, 159.
3
(
(
(
4) Kiec-Kononowicz, K.; Szymanska, E.; Motyl, M.; Holzer,
W.; Bialecka, A.; Kasprowicz, A. Pharmazie 1998, 53, 680.
5) Trivedi, S. D.; Kubawat, H. T.; Parekh, H. H. J. Indian
Chem. Soc. 2002, 79, 282.
6) Okazaki, T.; Kikuchi, K.; Watanable, T.; Suga, A.;
Shibasaki, M.; Fujimori, A.; Inagaki, O.; Yanagisawa, I.
Chem. Pharm. Bull. 1998, 46, 777.
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3
C NMR (400 MHz, DMSO-d ): d = 165.3 (C=O), 159.8 (C ),
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52.7 (C ), 141.9, 139.9, 138.1, 133.4, 132.7, 130.3, 129.2, 128.7,
25.7, 123.8, 119.5, 114.3 (ArC), 21.4 (CH3).
2
+
MS: m/z (%) = 370 (9), 368 (24) [M ], 340 (31), 253 (14), 132 (100).
Anal. Calcd for C H ClN OS: C, 58.62; H, 3.55; N, 15.19. Found:
C, 58.48; H, 3.65; N, 15.13.
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(7) Loukaci, A.; Guyot, M.; Chiaroni, A.; Riche, C. J. Nat. Prod.
1
998, 61, 519.
7
k
(
8) Sato, H.; Tsuda, M.; Watanabe, K.; Kobayashi, J.
Yellow crystals; mp 232–234 °C.
Tetrahedron 1998, 54, 8687.
Synthesis 2004, No. 7, 1067–1071 © Thieme Stuttgart · New York