K. Sharma, S. Khandelwal, R. M. Samarth, and M. Kumar
Vol 000
NMR (dimethyl sulfoxide d6) δ: 2.36 (s, 3H, CH3), 2.54 (s, 3H,
CH3), 6.90–7.89 (m, 6H, Ar–H), 8.35 (s, NH), 10.80(s, CONH);
13C (dimethyl sulfoxide d6) δ: 17.4 (CH3), 18.1(CH3), 115.9
(NHCO–C=C), 116.5 (ArC), 119.9 (ArC), 121.2 (ArC), 122.1
(ArC), 122.4 (ArC), 122.8 (ArC), 127.5 (ArC), 132.2 (ArC),
133.2 (ArC), 135.0 (NHCO–C=C), 147.5 (ArC), 170.4 (CO);
ms (m/z): 294 [M+]. Anal. Calcd. (%) for C17H14N2OS: C,
69.36; H, 4.79; N, 9.52. Found: C, 69.34; H, 4.76; N, 9.50.
2,11-Dimethyl-6,12-dihydroquino[3,4-b][1,4]benzothiazin-6
136.4 (S–C=C), 143.7 (ArC), 147.5 (ArC), 164.4 (C=N), 169.5
(C=O); ms (m/z): 381 [M+]. Anal. Calcd. (%) for C23H15N3OS: C,
72.42; H, 3.96; N, 11.02. Found: C, 72.44; H, 3.93; N, 11.0.
4, 16-Dimethyl-17H-quinazo[2´,3´:2,1]quino[3,4-b][1,4]ben-
zothiazine-6-one (4b).
Mp 315–317°C; ir (potassium
bromide): 3280, 3010, 2885, 1672, 1605, 1570, 760 cmꢁ1
;
1H
NMR (dimethyl sulfoxide d6) δ: 2.35 (s, 3H, CH3), 270 (s, 3H,
CH3), 6.35–6.50 (m, 4H, Ar–H), 6.69–7.12 (m, 3H, Ar–H),
7.35–7.52 (m, 3H, Ar–H), 8.40 (s, 1H, NH); ms (m/z): 395
[M+]. Anal. Calcd. (%) for C24H17N3OS: C, 72.89; H, 4.33;
N,10.63. Found: C, 72.44; H, 4.22; N, 10.54.
(5H)-one(3c).
Yield: 68%, mp 284–286°C; ir (potassium
bromide): 3410, 3340, 2890, 1685, 1622, 1492, 816 cmꢁ1; H
NMR (dimethyl sulfoxide d6) δ: 2.31 (s, 3H, CH3), 2.50 (s,
3H, CH3), 7.02–7.53 (6H, m, Ar–H), 8.41 (s, 1H, NH), 10.91
(s, 1H, CONH). 13C NMR (DMSO-d6) δ: 17.42 (CH3), 18.0
(CH3), 115.9 (NHCO–C=C), 116.5 (ArC), 119.9 (ArC), 121.2
(ArC), 122.1 (ArC), 122.4 (ArC), 122.8 (ArC), 127.5 (ArC),
132.2 (ArC), 133.2 (ArC), 135.0 (NHCO–C=C), 147.5 (ArC),
170.4 (CO). ms (m/z): 294 [M+]. Anal. Calcd. (%) for
C17H14N2OS: C, 69.36; H, 4.79; N, 9.52. Found: C, 69.39; H,
4.78; N, 9.54.
1
2,16-Dimethyl-17H-quinazo[2´,3´:2,1]quino[3,4-b][1,4]ben-
zothiazin-6-one (4c). Mp 310–312°C; ir (potassium bromide):
3270, 3050, 2882, 1670, 1608,1560, 765 cmꢁ1
;
1H NMR
(dimethyl sulfoxide d6) δ: 2.30 (3H, s, CH3), 2.75 (3H, s, CH3),
6.38–6.50 (m, 4H, Ar–H), 6.70–7.08 (m, 3H, Ar–H), 7.32–7.43
(m, 3H, Ar–H), 8.55 (1H, s, NH); 13C NMR (dimethyl sulfoxide
d6) δ: 15.6 (CH3), 18.09 (CH3), 99.1 (S–C=C), 118.7 (ArC),
119.8 (ArC), 120.6 (ArC), 123.1 (ArC), 124.5 (ArC), 125.2
(ArC), 125.7 (ArC), 126.2 (ArC), 126.6 (ArC), 126.8 (ArC),
127.4 (ArC), 127.7 (ArC), 128.4 (ArC), 128.9 (ArC), 132.7
(ArC), 133.7 (ArC), 134.8 (S–C=C), 146.8 (ArC), 147.5 (ArC),
164.4 (C=N), 169.5 (C=O). Anal. Calcd. (%) for C24H17ON3S:
C, 72.89; H, 4.33; N, 10.63. Found: C, 72.74; H, 4.32; N, 10.60.
4-Methoxy-14-methyl-17H-quinazo[2´,3´:2,1]quino[3,4-b][1,4]
4-Methoxy-9-methyl-6,12-dihydroquino[3,4-b][1,4]benzothiazin-
6(5H)-one (3d).
Yield: 74%, mp 288–290°C; ir (potassium
bromide): 3425, 3330, 2830, 1680, 1620, 1450, 1232, 780 cmꢁ1; 1H
NMR (dimethyl sulfoxide d6) δ: 2.41 (s, 3H, CH3), 3.80 (s, 3H,
OCH3), 6.92–7.95 (m, 6H, Ar–H), 8.55 (s, 1H, NH), 11.71 (s, 1H,
CONH). Anal. Calcd. (%) for C17H14N2O2S: C, 65.79; H, 4.55; N,
9.03. Found: C, 68.67; H, 4.42; N, 8.89.
benzothiazine-6-one (4d).
Mp 312–314°C; ir (potassium
bromide): 3350, 3020, 2920, 1660, 1610, 1580, 790 cmꢁ1
;
1H
11-Methoxy-2-methyl-6,12-dihydroquino[3,4-b][1,4]benzothiazin-
NMR (dimethyl sulfoxide d6) δ: 2.60 (s, 3H, CH3), 3.72 (s, 3H,
OCH3), 6.34–6.50 (m, 4H, Ar–H), 6.70–6.90 (m, 3H, Ar–H),
7.25–7.40 (m, 3H, Ar–H), 8.58 (s, 1H, NH); 13C NMR (dimethyl
sulfoxide d6) δ: 18.8 (CH3), 57.3 (OCH3), 99.2 (S–C = C), 112.8
(ArC), 114.9 (ArC), 117.7 (ArC), 119.5 (ArC), 120.3 (ArC),
122.4 (ArC), 125.2 (ArC), 126.0 (ArC), 126.5 (ArC), 126.7
(ArC), 127.1 (ArC), 127.7 (ArC), 128.6 (ArC), 128.9 (ArC),
133.7 (ArC), 134.9 (S–C=C), 146.8 (ArC), 147.5 (ArC), 154.5
(ArC), 164.2 (C=N), 169.5 (C=O). Anal. Calcd. (%) for
C24H17N3O2S: C, 70.05; H, 4.16; N, 10.21. Found: C, 69.97; H,
4.05; N, 10.13.
6(5H)-one (3e).
Yield: 72%, mp 288–290°C; ir (potassium
bromide): 3400, 3340, 2870, 1685, 1615, 1450, 1230, 790 cmꢁ1; 1H
NMR (dimethyl sulfoxide d6) δ: 2.52 (s, 3H, CH3), 3.74 (s, 3H,
OCH3), 6.94–7.95 (m, 6H, Ar–H), 8.53 (s, 1H, NH), 10.97 (s, 1H,
CONH); ms (m/z): 310 [M+]. Anal. Calcd. (%) for C17H14N2O2S: C,
65.79; H, 4.55; N, 9.03. Found: C, 35.68; H, 4.43; N, 8.91.
4,11-Dimethoxy-6,12-dihydroquino[3,4-b][1,4]benzothiazin-
6(5H)-one (3f).
bromide): 3390, 3325, 2880,1680, 1610, 1490, 1250,
810 cmꢁ1 1H NMR (dimethyl sulfoxide d6) δ: 3.84 (s, 3H,
Yield: 70%, mp 292–294°C; ir (potassium
;
OCH3), 4.12 (s, 3H, OCH3), 6.89–7.91 (m, 6H, Ar–H), 8.53 (s,
1H, NH), 11.73 (s, 1H, CONH); 13C (dimethyl sulfoxide d6) δ:
54.6 (OCH3), 55.7 (OCH3), 110.6 (ArC), 115.8 (NHCO–C=C),
119.9 (ArC), 120.2 (ArC), 121.2 (ArC), 122.3 (ArC), 122.4
(ArC), 127.5 (ArC), 133.2 (ArC), 135.2 (NHCO–C=C), 147.5
(ArC), 156.0 (ArC), 158.2 (ArC), 169.6 (CO); ms (m/z): 326
[M+]. Anal. Calcd. (%) for C17H14N2O3S: 62.56; H, 4.32; N,
8.58. Found: C, 62.57; H, 4.29; N, 8.60.
16-Methoxy-2-methyl-17H-quinazo[2´,3´:2,1]quino[3,4-b][1,4]
benzothiazine-6-one (4e).
Mp 317–319°C; ir (potassium
bromide): 3310, 3012, 2890, 1680, 1620, 1565, 782 cmꢁ1
;
1H
NMR (dimethyl sulfoxide d6) δ: 2.64 (s, 3H, CH3), 3.54 (s, 3H,
OCH3), 6.42–6.66 (m, 4H, Ar–H), 6.68–6.85 (m, 3H, Ar–H),
7.30–7.42 (m, 3H, Ar–H), 8.61 (s, 1H, NH); ms (m/z): 411 [M+].
Anal. Calcd. (%) for C24H17N3O2S: C, 70.05; H, 4.16; N, 10.21.
Found: C, 69.02; H, 4.08; N, 10.11.
2-Methyl-6,12-dihydroquino[3,4-b][1,4]benzothiazin-6(5H)-
4,16-Dimethoxy-17H-quinazo[2´,3´:2,1]quino[3,4-b][1,4]ben-
zothiazine-6-one (4f). Mp 325–327°C; ir (potassium bromide):
one (3g).
Yield: 60%, mp 278–280°C; ir (potassium
1
bromide): 3445, 3340, 2912, 1685, 1628, 1520, 828 cmꢁ1; H
NMR (DMSO-d6) δ: 2.50 (s, 3H, CH3), 6.80–7.54 (m, 7H,
Ar–H), 8.30 (s, 1H, NH), 10.92 (s, 1H, CONH). Anal. Calcd.
for C16H12N2OS: C, 68.55; H, 4.31; N, 9.99. Found: C, 68.46;
H, 4.21; N, 9.83.
3325, 3015, 2900, 1660, 1625, 1570, 780 cmꢁ1 1H NMR
;
(dimethyl sulfoxide d6) δ: 3.38 (s, 3H, OCH3), 3.58 (s, 3H,
OCH3), 6.35–6.55 (m, 4H, Ar–H), 6.67–6.92 (m, 3H, Ar–H),
7.35–7.60 (m, 3H, Ar–H), 8.72 (s, 1H, NH); ms (m/z): 427
[M+]. Anal. Calcd. (%) for C24H17N3O3S: C, 67.43; H, 4.01; N,
9.83. Found: C, 67.35; H, 3.94; N, 9.74.
14-Methyl-17H-quinazo[2´,3´:2,1]quino[3,4-b][1,4]benzothiazin-
6-one (4a). Mp 310–312°C; ir (potassium bromide): 3260, 3000,
2-Methyl-17H-quinazo[2´,3´:2,1]quino[3,4-b][1,4]benzothia-
zine-6-one(4g). Mp 306–308°C; ir (potassium bromide): 3240,
1
2880, 1670, 1600, 1550, 750 cmꢁ1; H NMR (dimethyl sulfoxide
d6) δ: 2.33 (s, 3H, CH3), 6.58–6.73 (m, 4H, Ar–H), 7.18–7.32 (m,
4H, Ar–H), 7.38–7.49 (m, 3H, Ar–H), 8.51 (s, 1H, NH); 13C
(dimethyl sulfoxide d6) δ: 18.1 (CH3), 99.4 (S–C=C), 115.9 (ArC),
119.4 (ArC), 120.1 (ArC), 122.8 (ArC), 125.2 (ArC), 126.1 (ArC),
126.5 (ArC), 126.8 (ArC), 127.3 (ArC), 127.5 (ArC), 127.9 (ArC),
128.7 (ArC), 129.4 (ArC), 130.2 (ArC), 132.8 (ArC), 134.1 (ArC),
3008, 2870, 1670, 1555, 1542, 746 cmꢁ1 1H NMR (dimethyl
;
sulfoxide d6) δ: 2.65 (s, 3H, CH3), 6.36–6.90 (m, 4H, Ar–H),
6.70–7.35 (m, 4H, Ar–H), 7.14–7.7.40 (m, 3H, Ar–H), 8.38 (s,
1H, NH); ms (m/z): 427 [M+]. Anal. Calcd. (%) for
C23H15N3OS: C, 72.42; H, 3.96; N, 11.02. Found: C, 72.29; H,
3.94; N, 10.88.
© 2015 HeteroCorporation