Novel SO3H‑functionalized…
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CH2), 3.27 (1H, AB System, dd, 2JHH=19.2 and JHH =2.2 Hz, CH), 3.47 (1H, AB
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System, dd, JHH=19.2 and JHH =1.1 Hz, CH), 4.03 (3H, s, OCH3), 6.41 (1H, s,
CH), 7.45 (1H, d, 4JHH =2 Hz, CH), 7.58 (1H, d, 4JHH =2 Hz, CH), 7.89–7.93 (2H,
m, 2CH), 8.27–8.31 (1H, m, CH), 8.38–8.42 (1H, m, CH), 10.74 (1H, s, OH) ppm;
13C NMR (CDCl3, 100 MHz): δ=28.3, 28.8, 34.7, 38.1, 50.9, 56.9, 64.1, 113.4,
117.1, 118.3, 127.7, 128, 128.3, 128.7, 129, 133.8, 133.9, 134.8, 146.6, 150.1,
151.7, 154.8, 156, 192.3 ppm; Anal. Calcd for C24H21N3O7 (463.43): C, 62.2; H,
4.57; N, 9.07. Found: C, 62.28; H, 4.51; N, 9.12%.
3,4‑Dihydro‑3,3‑dimethyl‑13‑(3,4,5‑trimethoxyphenyl)‑2H‑indazolo[2,1‑b]phthala‑
zine‑1,6, 11(13H)‑trione (8h) Yield: 0.42 g (91%); M.P.=234–236 °C (lit. [50]
233–235 °C); IR (KBr): ̄ꢀ =2959, 2838, 1659, 1466, 1363, 1314, 1266, 699 cm−1;
1H NMR (CDCl3, 400 MHz): δ=1.25 (3H, s, CH3), 1.26 (3H, s, CH3), 2.38 (2H, s,
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CH2), 3.23 (1H, AB System, dd, 2JHH=19.1 and JHH =2.1 Hz, CH), 3.48 (1H, AB
System, d, 2JHH=19.1 Hz, CH), 3.82 (3H, s, OCH3), 3.84 (6H, s, 2OCH3), 6.42 (1H,
s, CH), 6.65 (2H, s, 2CH), 7.88–7.89 (2H, m, 2CH), 8.31–8.33 (1H, m, CH), 8.37–
8.39 (1H, m, CH) ppm; 13C NMR (CDCl3, 100 MHz): δ=28.2, 28.9, 29.4, 34.6,
38.1, 50.9, 56.1, 56.2, 60.7, 65, 104.7, 118.4, 127.8, 128, 128.9, 129.1, 131.8, 133.6,
134.6, 150.9, 153.4, 192.2 ppm; Anal. Calcd for C26H26N2O6 (462.49): C, 67.52; H,
5.7; N, 6.06. Found: C, 67.61; H, 5.76; N, 6.02%.
3,4‑Dihydro‑3,3‑dimethyl‑13‑(4‑bromophenyl)‑2H‑indazolo[2,1‑b]phthala‑
zine‑1,6,11 (13H)‑trione (8i) Yield: 0.40 g (87%); M.P.=261–263 °C (lit. [47] 262–
263 °C); IR (KBr): ̄ꢀ =2959, 1660, 1363, 1313, 1270, 697 cm−1; 1H NMR (CDCl3,
400 MHz): δ=1.22 (3H, s, CH3), 1.23 (3H, s, CH3), 2.36 (2H, s, CH2), 3.26 (1H,
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AB System, dd, JHH=19.1 and JHH =2.3 Hz, CH), 3.42 (1H, AB System, dd,
2JHH=19.1 and JHH =1.2 Hz, CH), 6.44 (1H, s, CH), 7.32 (2H, d, JHH=8.6 Hz,
2CH), 7.38 (2H, d, 3JHH=8.6 Hz, 2CH), 7.86–7.91(2H, m, 2CH), 8.28–8.3 (1H, m,
CH), 8.37–8.39 (1H, m, CH) ppm; 13C NMR (CDCl3, 100 MHz): δ=28.5, 28.7,
34.7, 38.1, 50.9, 64.4, 118.1, 127.8, 128.1, 128.5, 128.9, 133.7, 134.5, 134.6, 134.9,
151.1, 154.4, 156, 192.1 ppm; Anal. Calcd for C23H19BrN2O3 (451.32): C, 61.21; H,
4.24; N, 6.21; Br, 17.71. Found: C, 61.28; H, 4.2; N, 6.18; Br, 17.65%.
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3,4‑Dihydro‑3,3‑dimethyl‑13‑(4‑benzyloxyphenyl)‑2H‑indazolo[2,1‑b]phthala‑
zine‑1,6,11 (13H)‑trione (8j) Yield: 0.41 g (83%); M.P.=223–225 °C (lit. [51]
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221 °C); IR (KBr): ̄ꢀ =2959, 1660, 1511, 1364, 1314, 1273, 699 cm−1; H NMR
(CDCl3, 400 MHz): δ=1.23 (3H, s, CH3), 1.25 (3H, s, CH3), 2.37 (2H, s, CH2), 3.26
(1H, AB System, dd, 2JHH=19.1 and 4JHH =2.3 Hz, CH), 3.44 (1H, AB System, dd,
2JHH=19.1 and 4JHH =1.2 Hz, CH), 5.03 (2H, s, CH2O), 6.45 (1H, s, CH), 6.95–6.97
(2H, m, 2CH), 7.35–7.42 (7H, m, 7CH), 7.85–7.88 (2H, m, 2CH), 8.28–8.31 (1H,
m, CH), 8.36–8.38 (1H, m, CH) ppm; 13C NMR (CDCl3, 100 MHz): δ=28.6, 28.7,
34.7, 38.1, 51, 64.6, 70, 114.9, 118.6, 127.5, 127.7, 127.95, 127.98, 128.54, 128.58,
128.63, 129, 129.2, 133.5, 134.5, 136.9, 150.8, 154.3, 156.1, 159.1, 192.2 ppm;
Anal. Calcd for C30H26N2O4 (478.53): C, 75.29; H, 5.48; N, 5.86. Found: C, 75.31;
H, 5.49; N, 5.81%.
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