1
76
Salehi and Guo
51.9, 56.0, 59.4, 102.9, 115.0, 127.2, 134.6, 149.9, 153.1, 156.6, 165.6. Anal.
Calcd. For C H N O : C, 62.05; H, 6.24; N, 9.64; Found: C, 61.93; H, 6.27;
1
5 18 2 4
þ
N, 9.44. MS: m/z ¼ 290.1 (M ), 275, 261, 217, 197, 169, 151, 94, 56.
21 1
4
g. m.p. 2068C. IR (KBr): n ¼ 3245, 3118, 2978, 1725, 1701,
1
649 cm . HNMR (DMSO-d ): d ¼ 1.06 (t, 3H, J ¼ 6.84, CH ), 2.24 (s,
6
3
3
H, CH ), 3.94 (q, 2H, J ¼ 6.75, CH ), 5.13 (d, 1H, J ¼ 3.06, H-4), 7.21–7.37
3
2
(
m, 5H, H
M ), 232, 231, 213, 187, 183, 155, 137, 115, 102, 77.
), 7.73 (brs, 1H, NH), 9.19 (brs, 1H, NH). MS: m/z ¼ 260.1
arom
þ
(
4
h. m.p. 198–2008C. IR (KBr): n ¼ 3436, 3247, 3113, 2929, 1724,
2
1 1
1
705, 1649 cm . HNMR (DMSO-d ): d ¼ 1.10 (t, 3H, J ¼ 7.08 CH ), 2.17
6
3
(
s, 3H, CH ), 3.71 (s, 3H, CH ), 3.96 (q, 2H, J ¼ 7.14, CH ), 5.07 (d, 1H,
3
3
2
J ¼ 2.97, H-4), 6.85 (d, 2H, J ¼ 8.49, H
), 7.12 (d, 2H, J ¼ 8.55, H
),
arom
arom
7
.67 (brs, 1H, NH), 9.15 (brs, 1H, NH).
4
i. m.p. 206–2088C. IR (KBr): n ¼ 3342, 3242, 3117, 2985, 1700,
2
1 1
1
645 cm . HNMR (DMSO-d ): d ¼ 1.05 (t, 3H, J ¼ 7.08, CH ), 2.22 (s,
6
3
3
H, CH ), 3.98 (q, 2H, J ¼ 6.99, CH ), 5.19 (d, 1H, J ¼ 3.0, H-4), 6.08 (d, 1H,
3
2
J ¼ 2.94, H
), 6.35 (s, 1H, H
), 7.55 (s, 1H, H
), 7.76 (brs, 1H, NH),
arom
arom
arom
þ
9
.25 (brs, 1H, NH). MS: m/z ¼ 250.09 (M ), 233, 221, 205, 177, 176, 124.
4
j. m.p. 226–2288C. IR (KBr): n ¼ 3422, 3104, 2964, 1708, 1690, 1630,
2
1 1
1
3
526 cm . HNMR (DMSO-d ): d ¼ 1.08 (t, 3H, J ¼ 7.02, CH ), 2.27 (s,
6 3
H, CH ), 3.98 (q, 2H, J ¼ 4.57, CH ) 5.30 (d, 1H, J ¼ 2.69, H-4), 7.63-7.72
3
2
(
m, 2H, H
), 7.93 (brs, 1H, NH), 8.09–8.16 (m, 2H, H
), 9.40 (brs, 1H,
arom
arom
þ
NH). MS: m/z ¼ 305.1 (M ), 289, 288, 276, 260, 232, 183, 155, 137, 110.
4
k. m.p. 2328C. IR (KBr): n ¼ 3511, 3278, 3123, 2975, 1686,
2
1 1
1
3
2
647 cm . HNMR (DMSO-d ): d ¼ 1.07 (t, 3H, J ¼ 6.90, CH ), 2.22 (s,
6
3
H, CH ), 3.93 (q, 2H, J ¼ 6.98, CH ) 5.03 (d, 1H, J ¼ 2.76, H-4), 6.67 (d,
3
2
H, J ¼ 8.25, H
), 7.01 (d, 2H, J ¼ 8.32, H
), 7.62 (brs, 1H, NH), 9.12
arom
arom
(
brs, 1H, NH), 9.32 (brs, 1H, OH).
4
l. m.p. 248–2508C. IR (KBr): n ¼ 3359, 3220, 3105, 2971, 1698, 1644,
2
1 1
1
590 cm . HNMR (DMSO-d ): d ¼ 1.04 (t, 3H, J ¼ 7.04, CH ), 2.28 (s,
6
3
3
H, CH ), 3.87 (q, 2H, J ¼ 6.99, CH ), 5.59 (brs, 1H, H-4), 7.29 (d, 1H,
3
2
J ¼ 8.26, H
), 7.39 (d, 1H, J ¼ 8.27, H
), 7.55 (brs, 1H, H
), 7.77
arom
arom
arom
(
brs, 1H, NH), 9.33 (brs, 1H, NH). MS: m/z ¼ 300, 299, 293, 263, 257, 255,
1
83, 155, 137, 110, 58, 43.
4
m. m.p. 240–2428C. IR (KBr): n ¼ 3247, 3115, 2928, 1720, 1701,
2
1 1
1
3
652 cm . HNMR (DMSO-d ): d ¼ 1.17 (t, 3H, J ¼ 7.05, CH ), 2.19 (s,
3 2
6
3
H, CH ), 4.06 (q, 2H, J ¼ 7.17, CH ) 4.72 (brs, 1H, H-4), 6.20 (dd, 1H,
J ¼ 5.86, J ¼ 6, 55 CH), 6.33 (d, 1H, J ¼ 15.86, 55 CH), 7.22–7.41 (m, 5H,
þ
H
), 7.56 (brs, 1H, NH), 9.15 (brs, 1H, NH). MS: m/z ¼ 286.1 (M ), 258,
arom
2
57, 240, 213, 211, 183, 155, 137, 104, 103, 91, 78.
n. m.p. 206–2088C. IR (KBr): n ¼ 3328, 3173, 3104, 2979, 1670,
4
2
1 1
1
573, 1465 cm . HNMR (DMSO-d ): d ¼ 1.07 (t, 3H, J ¼ 7.08, CH ), 2.28
6
3