Molecular Iodine: A Versatile Catalyst
1002
3,4-Dihydro-3,3-dimethyl-13-(4-methylphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,
11(13H)-trione (4d)
1H NMR (CDCl3, 400 MHz) δ: 8.37-8.27 (m, 2H), 7.87-7.83 (m, 2H), 7.31 (d, 2H, J = 8.0 Hz), 7.15
(d, 2H, J = 7.6 Hz), 6.43 (s, 1H), 3.43 (d, 1H, J = 18.8 Hz), 3.25 (dd, 1H, J = 2.0, 18.8 Hz), 2.34
(s, 2H), 1.22 (s, 6H); 13C NMR (CDCl3, 100 MHz) δ: 192.2, 156.0, 154.2, 150.7, 138.5, 134.4, 133.4,
133.3, 129.4, 129.1, 127.9, 127.7, 118.7, 64.8, 51.0, 38.0, 34.6, 28.7, 28.4, 21.2; MS (ESI) m/z 387
(M+1); Anal. calcd for C24H22N2O3:C 74.59, H 5.74, N 7.25; found: C 74.62, H 5.69, N 7.37.
3,4-Dihydro-3,3-dimethyl-13--(4-nitrophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,
11(13H)-trione (4e)
1H NMR (CDCl3, 400 MHz) δ: 8.40-8.24 (m, 2H), 8.21 (d, 2H, J = 8.8 Hz), 7.90 (dd, 2H,
J = 1.6, 5.6 Hz), 7.62 (d, 2H, J = 8.8 Hz), 6.52 (s, 1H), 3.42 (d, 1H, J = 19.2 Hz), 3.27
(dd, 1H, J = 2.0, 19.2 Hz), 2.34 (s, 2H), 2.31 (s, 3H), 1.29-1.20 (s, 6H); 13C NMR (CDCl3,
100 MHz) δ: 192.0, 155.9, 154.5, 151.6, 147.9, 143.4, 134.8, 133.9, 128.9, 128.6, 128.2,
128.0, 127.8, 124.0, 117.3, 64.1, 50.8, 38.0, 34.7, 28.7, 28.4; MS (ESI) m/z 418 (M+1);
Anal. calcd for C23H19N3O5: C 66.18, H 4.59, N 10.07; found: C 66.21, H 4.50, N 10.01.
3,4-Dihydro-3,3-dimethyl-13--(3-nitrophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,
11(13H)-trione (4f)
1H NMR (CDCl3, 400 MHz) δ: 8.41-8.25 (m, 2H), 8.18 (d, 2H, J = 7.2 Hz), 7.92-7.89
(m, 3H), 7.57 (t, 1H, J = 7.2 Hz), 6.54 (s, 1H), 3.45 (d, 1H, J = 19.6 Hz), 3.29 (dd, 1H,
J = 2.0, 19.6 Hz), 2.36 (s, 2H), 1.27-1.19 (s, 6H); 13C NMR (CDCl3, 100 MHz) δ: 192.1,
156.0, 154.6, 151.8, 148.5, 138.6, 134.8, 134.2, 133.9, 129.7, 129.0, 128.6, 128.2, 127.7,
123.7, 121.5, 117.1, 64.1, 50.8, 38.0, 34.7, 28.7, 28.4; MS (ESI) m/z 418 (M+1); Anal. calcd
for C23H19N3O5: C 66.18, H 4.59, N 10.07; found: C 66.18, H 4.65, N 10.05.
3,4-Dihydro-3,3-dimethyl-13--(4-fluorophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,
11(13H)-trione (4g)
1H NMR (CDCl3, 400 MHz) δ: 8.37-8.26 (m, 2H), 7.88-7.85 (m, 2H), 7.43-7.39 (m, 2H),
7.03 (t, 2H, J = 8.8 Hz), 6.44 (s, 1H), 3.42 (d, 1H, J = 18.8 Hz), 3.25 (dd, 1H, J = 2.4,
18.8 Hz), 2.35 (s, 2H), 1.27-1.22 (s, 6H); 13C NMR (CDCl3, 100 MHz) δ: 192.1, 163.9,
161.5, 156.0, 154.4, 151.0, 134.6, 133.6, 132.2, 129.0, 128.9, 128.0, 127.7, 118.2, 115.8,
115.6, 64.3, 50.9, 38.0, 34.6, 28.7, 28.4; MS (ESI) m/z 391 (M+1); Anal. calcd for
C23H19FN2O3: C 70.76, H 4.91, N 7.18; found: C 70.82, H 4.88, N 7.26.
3,4-Dihydro-3,3-dimethyl-13-(2-chlorophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,
11(13H)-trione (4h)
1H NMR (CDCl3, 400 MHz) δ: 8.39-8.25 (m, 2H), 7.89-7.84 (m, 2H), 7.49 (d, 1H,
J = 6.8Hz), 7.34-7.22 (m, 3H), 6.69 (s, 1H), 3.42 (d, 1H, J = 18.8 Hz), 3.25 (dd, 1H, J = 2.0,
18.8 Hz), 2.33 (s, 2H), 1.27-1.22 (m, 6H); 13C NMR (CDCl3, 100 MHz) δ: 192.1, 156.2,
154.2, 151.8, 134.5, 133.6, 133.0, 132.5, 130.5, 129.9, 129.0, 128.7, 128.0, 127.7, 127.2,
64.1, 50.8, 38.0, 34.6, 28.8, 28.4; MS (ESI) m/z 407 (M+1); Anal. calcd for C23H19ClN2O3: C
67.90, H 4.71, N 6.89; found: C 70.02, H 4.69, N 6.95.
3,4-Dihydro-3,3-dimethyl-13-(2,4-dichlorophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,
11(13H)-trione (4i)
1H NMR (CDCl3, 400 MHz) δ: 8.38-8.24 (m, 2H), 7.90-7.86 (m, 2H), 7.43 (d, 2H,
J = 8.0Hz), 7.35-7.27 (m, 2H), 6.64 (s, 1H), 3.40 (d, 1H, J = 18.8 Hz), 3.25 (dd, 1H, J = 2.4,