1826 Farhat et al.
Asian J. Chem.
CH3
NC
S
NC
N
CH3
O
NC
H
NH2
Ph
N
PhHN
Ph
O
N
Ac2O
N
H
S
H
N
H3C
N
S
Ac2O
O
AcOH
H3C
(5)
O
O
CH3
O
O
N
NC
(10a)
N
H
N
N
NH
NH2
NH
H
PhHN
S
NC
CH3
OH
HN
O
NC
O
(12)
Ph
N
NC
NC
N
S
N
CH3
H
N
Ph
PhHN
CHOCH2CH3
N
H3C
S
(10a)
PhHN
H
N
N
O
O
S
O
HC(OEt)3
S
H3C
(13)
N
H
O
O
O
N
H
NC
(5)
N
PhHN
Fig. 4
N
S
(14)
O
NH
Scheme-IV
TABLE-1
PHYSICAL AND SPECTRAL DATA OF SYNTHESIZED COMPOUNDS
Compd.
No.
m.p. (°C),
yield (%)
1H NMR (ppm)
13C NMR (ppm)
IR (νmax, cm–1)
10.30 (s, 1H, NH), 7.50-7.15 (m, 5H,
Ph), 6.80 (br, 2H, NH2), 3.65 (s, 3H,
CH3)
163.10 (CO), 162.76, 154.14, 140.06,
129.42, 125.00, 121.22, 81.60, 80.71, (Ar-
C), 113.67 (CN), 50.69 (CH3)
244-246,
(80)
3441-3338 (NH2, NH), 2206
3a
3b
3c
(CN), 1661 (COester
)
3420-3325 (NH2), 3270
(NH), 2206 (CN), 1654
10.30 (s, 1H, NH), 7.46-7.15 (m, 5H,
Ph), 6.75 (br, 2H, NH2), 4.13 (q, 2H,
CH2), 1.18 (t, 3H, CH3)
162.81 (CO), 162.81, 154.16, 140.16,
129.45, 125.02, 120.20, 81.78, 80.70, (Ar-
C), 113.73 (CN), 59.20 (CH2), 14.42 (CH3)
212-214,
(82)
(COester
)
3420, 3325 (NH2), 3277
(NH), 2206 (CN),
10.00 (s, 1H, NH), 7.45-7.30 (m, 5H,
Ph), 6.73 (br, 2H, NH2), 4.98 (heptet,
1H, CH), 1.20 (d, 6H, 2CH3)
162.85 (CO), 162.45, 154.30, 140.12,
129.45, 125.07, 121.43, 81.70, 81.00 (Ar-
C), 113.69 (CN), 66.50 (CH), 22.00 (2CH3)
202-204,
(69)
1654 (COester
)
10.30 (s, 1H, NH), 7.507.15 (m, 5H,
3420-3325 (NH2), 3277 (NH) Ph), 6.75 (br, 2H, NH2), 4.10 (t, 2H,
162.83 (CO), 162.80, 154.16, 140.10,
129.44, 125.04, 121.34, 81.72, 80.71, (Ar-
C), 113.68 (CN), 59.18, (CH2), 30.42 (CH2),
18.58 (CH2), 13.48 (CH3)
124-126,
(57)
3d
5
2200 (CN) 1654 (COester
)
CH2), 1.50 (pentet, 2H, CH2), 1.30
(six., 2H, CH2), 0.85 (q, 3H, CH3)
294-296
Lit. [17],
296-298,
(59)
171.30 (CO, oxazinone), 166.16 (CON),
157.06, 154.54, 154.39, 138.53, 131.26,
130.25, 128.22, 107.18, 91.40, , (Ar-C),
109.39 (CN), 23.319 (CH3), 20.93 (CH3)
2207 (CN), 1758 (CO), 1690 7.73-7.58 (m, 5H, Ph), 4.40 (s, 3H,
(CO) CH3), 2.05 (s, 3H, CH3)
171.76 (CO), 171.66 (CO), 160.86 (CO),
153.39 (CO), 141.28, 139.93, 139.92,
OCH2), 2.22 (s, 6H, 2COCH3), 2.09 (s, 132.07, 131.39, 130.76, 120.80, 98.27
3434 (NH), 3344 (NH), 3257 7.727.59 (m, 5H, Ph), 4.30 (q, 2H,
(NH), 2221 (CN), 1719 br.,
(3CON, 1684 (COester
153-155,
(67)
6
)
3H, COCH3), 1.30 (t, 3H, CH3)
(Ar-C), 110.50 (CN), 62.33 (OCH2), 25.95,
25.57, 23.48, 14.41 (4 CH3)
164.74 (CO), 161.69 (CO), 160.18, 140.18,
129.65, 125.22, 121.11, 112.50, 102.64,
88.64 (Ar-C), 113.15 (CN), 60.69 (OCH2),
42.38 (CH2Cl), 14.03 (CH3)
10.39 (br, 2H, 2NH), 7.51-7.16 (m, 5H,
Ph), 4.40 (s, 2H, CH2Cl), 4.19 (q,
2HOCH2), 1.23 (t, 3H, CH3)
258-260,
(72)
3250, br. (2NH), 2220 (CN),
1690br. (2C=Oester
7
9
)
161.74 (CO), 160.60, 141.89, 138.66,
130.03, 126.04, 120.87, 101.40, 86.40
(Ar-C), 112.87 (CN), 61.41 (OCH2), 14.38
(CH3)
7.70 (br, 1H, NH), 7.50-7.20 (m, 5H,
Ph), 4.31 (q, 2H, OCH2), 1.34 (t, 3H
(CH3)
163-165,
(98)
3255 (NH), 2220 (CN), 2132
(N3), 1695 (CO)
10.80 (s, 1H pyrroleNH), 10.05 (br,
1H, NH), 7.55 (1H, pyrrole H), 7.45-
7.0 (m, 5H, Ph), 6.95 (s, 1H, CONH),
3467 (NH), 3342, 3266
(NH2), 3204 (NH), 3209
234-237,
(43)
163.70 (CO), 114.04 (CN), 159.56-82.22
(Ar-C), 39.95 (NCH2), 25.50 (CH2)
10a
(NH), 2213 (CN), 1606 (CO) 6.75 (br, 2H, NH2), 3.40 (t, 2H, NCH2),
2.85 (t, 2H, CH2)
9.05 (br, 1H, NH), 7.50-7.10 (m, 5H,
3414, 3300 (NH2), 3210
166.68 (CO), 160.56, 152.70, 141.52,
130.41, 125.42, 121.28, 88.02, 84.03
(Ar-C), 114.10 (CN), 47.29, 26.90, 25.35
(piperidyl-C).
143-145,
(68)
Ph), 6.23 (br, 2H, NH2), 3.52 (t, 4H,
(NH), 2200 (CN), 1658
10b
10c
2CH2), 1.63 (pentet, 4H, (2CH2), 1.55
(CO).
(pentet, 2H, CH2).
9.01 (br, 1H, NH), 7.50-7.15 (m, 5H,
3446, 3394 (NH2), 3341
164.29 (CO), 114.05 (CN), 160.22,
152.52, 141.68, 130.42, 125.60, 121.50,
87.83, 84.18, (Ar-C), 49.11, 33.89, 26.40,
26.14 (cyclohexyl-C).
190-192,
(91)
Ph), 6.50 (br, 2H, NH2), 6.25 (1H,
(NH), 3280 (NH), 2206
CONH), 3.80 (m, 1H, CH), 2.00-0.85
(CN).
(m, 10H, (5CH2), cyclohexyl).