Convenient Synthesis of New Indeno[1,2-c]pyridazines
G
3-(4-Chlorophenyl)-6-chloro-5H-indeno[1,2-c]
pyridazine (15l)
3-(3,4-Methylenedioxyphenyl)-6-chloro-5H-indeno
[1,2-c]pyridazine (15q)
Compound 15l was obtained as white needles, mp 245–
2468C. dH (300 MHz, CDCl3) 4.05 (s, 2H, CH2), 7.52 (s, 2H, Ar),
7.68 (d, J 7.8, 2H, Ar), 7.97–8.08 (m, 3H, Ar), 8.27 (s, 1H, Ar).
dC (75 MHz, CDCl3) 34.2, 120.1, 123.2, 125.6, 128.0, 128.1,
128.7, 129.8, 130.2, 132.2, 138.6, 139.6, 140.0, 155.4, 162.3.
nmax (KBr)/cmꢀ1 3074, 2910, 2889, 1598, 1518, 1441, 1068,
839, 717. Found C 65.24, H 3.23, N 9.04. C17H10Cl2N2 requires
C 65.20, H 3.22, N 8.94 %.
Compound 15q was obtained as white needles, mp 244–2458C.
dH (300 MHz, CDCl3) 4.02 (s, 2H, CH2), 6.07 (s, 2H, OCH2O),
6.96 (d, J 9.3, 1H, Ar), 7.50 (s, 2H, Ar), 7.61 (d, J 7.8, 1H, Ar), 7.75
(s, 1H, Ar), 7.93 (s, 1H, Ar), 8.25 (s, 1H, Ar). dC (75 MHz, CDCl3)
34.2, 101.5, 107.4, 108.6, 119.6, 119.8, 121.3, 125.3, 127.8, 129.7,
129.9, 137.7, 141.3, 142.8, 148.4, 149.0, 155.9, 161.4. nmax
(KBr)/cmꢀ1 2999, 2901, 2787, 1596, 1498, 1245, 1037, 821,
798. Found C 66.95, H 3.41, N 8.80. C18H11ClN2O2 requires
C 66.99, H 3.44, N 8.68 %.
3-(4-Fluorophenyl)-6-chloro-5H-indeno[1,2-c]
pyridazine (15m)
3-Phenyl-8-methoxy-5H-indeno[1,2-c]pyridazine (15r)
Compound 15m was obtained as white needles, mp
175–1768C. dH (300 MHz, CDCl3) 4.02 (s, 2H, CH2), 7.20
(d, J 7.5, 1H, Ar), 7.43–7.58 (m, 3H, Ar), 7.97 (s, 1H, Ar), 8.03–
8.19 (m, 2H, Ar), 8.24 (s, 1H, Ar). dC (75 MHz, CDCl3) 34.3,
115.1, 116.9, 119.9, 120.9, 126.2, 127.4, 128.1, 129.7, 130.0,
130.3, 130.6, 130.9, 131.7, 136.0, 140.8, 156.7, 161.1. nmax
(KBr)/cmꢀ1 3083, 2910, 2889, 1619, 1597, 1442, 1088, 839.
Found C 68.85, H 3.45, N 9.60. C17H10ClFN2 requires C 68.81,
H 3.40, N 9.44 %.
Compound 15r was obtained as yellow needles, mp
198–2008C. dH (300 MHz, CDCl3) 3.86 (s, 2H, CH2), 3.91
(s, 3H, OCH3), 7.04 (dd, J1 6, J2 2.1, 1H, Ar), 7.37–7.58
(m, 4H, Ar), 7.80 (s, 1H, Ar), 7.86 (s, 1H, Ar), 8.10 (d, J 6.9,
2H, Ar). dC (75 MHz, CDCl3) 33.9, 55.6, 104.9, 118.4, 120.1,
126.0, 127.1, 128.9, 129.6, 135.0, 137.0, 139.0, 142.4, 156.5,
159.8, 161.6. nmax (KBr)/cmꢀ1 3062, 2995, 2927, 2839, 1615,
1482, 1471, 1402, 1247, 1205, 1050, 791. Found C 78.79, H
5.12, N 10.32. C18H14N2O requires C 78.81, H 5.14, N 10.21 %.
3-(4-Methoxyphenyl)-6-chloro-5H-indeno[1,2-c]
pyridazine (15n)
3-(4-Bromophenyl)-8-methoxy-5H-indeno[1,2-c]
pyridazine (15s)
Compound 15n was obtained as white needles, mp 196–
1988C. dH (300 MHz, CDCl3)3.88 (s, 3H, OCH3), 3.98 (s, 2H,
CH2), 7.02 (d, J 8.7, 2H, Ar), 7.40–7.51 (m, 2H, Ar), 7.89 (s, 1H,
Ar), 8.08 (d, J 7.8, 2H, Ar), 8.18–8.25 (m, 1H, Ar). dC (75 MHz,
CDCl3) 34.2, 55.3, 114.3, 119.4, 120.0, 128.4, 129.0, 129.6,
129.7, 131.4, 139.7, 140.6, 140.7, 156.4, 160.5, 161.1. nmax
(KBr)/cmꢀ1 3024, 2931, 2893, 1600, 1511, 1442, 1408, 1250,
1223, 1158, 845. Found C 70.00, H 4.20, N 9.19. C18H13ClN2O
requires C 70.02, H 4.24, N 9.07 %.
Compound 15s was obtainedaswhite needles, mp 227–2288C.
dH (300MHz, CDCl3) 3.88 (s, 2H, CH2), 3.93 (s, 3H, OCH3), 7.06
(d, J 8.1, 1H, Ar), 7.46 (d, J 8.4, 1H, Ar), 7.63 (d, J 8.7, 2H, Ar),
7.80 (s, 1H, Ar), 7.86 (s, 1H, Ar), 7.98 (d, J 8.4, 2H, Ar). dC
(75 MHz, CDCl3) 33.9, 55.6, 105.0, 118.6, 119.8, 124.2, 126.0,
128.5, 132.1, 135.0, 135.9, 138.8, 142.5, 155.4, 159.9, 161.8. nmax
(KBr)/cmꢀ1 2990, 2965, 2901, 2838, 1598, 1465, 1392, 1234,
1051, 829. FoundC 61.23, H 3.70, N 8.07. C18H13BrN2O requires
C 61.21, H 3.71, N 7.93 %.
3-(3-Mehoxyphenyl)-6-chloro-5H-indeno[1,2-c]
pyridazine (15o)
3-(4-Chlorophenyl)-8-methoxy-5H-indeno[1,2-c]
pyridazine (15t)
Compound 15o was obtained as white needles, mp
150–1518C. dH (300 MHz, CDCl3) 3.88 (s, 3H, OCH3), 3.97
(s, 2H, CH2), 7.03 (dd, J1 6.6, J2 1.8, 1H, Ar), 7.38–7.55 (m, 3H,
Ar), 7.61 (d, J 7.5, 1H, Ar), 7.80 (s, 1H, Ar), 7.97 (s, 1H, Ar),
8.19–8.28 (m, 1H, Ar). dC (75 MHz, CDCl3) 34.3, 55.4, 112.1,
116.2, 119.3, 120.3, 129.7, 129.9, 130.0, 131.4, 138.1, 139.7,
140.7, 140.8, 156.7, 160.2, 161.3. nmax (KBr)/cmꢀ1 3074,
3007, 2973, 2939, 2838, 1609, 1582, 1457, 1393, 1273, 1050,
782. Found C 69.99, H 4.22, N 9.21. C18H13ClN2O requires C
70.02, H 4.24, N 9.07 %.
Compound 15t was obtained as yellow needles, mp
211–2138C. dH (300 MHz, CDCl3) 3.89 (s, 2H, CH2), 3.93
(s, 3H, OCH3), 7.07 (d, J 8.4, 1H, Ar), 7.47 (d, J 8.1, 3H, Ar),
7.81 (s, 1H, Ar), 7.86 (s, 1H, Ar), 8.04 (d, J 8.4, 2H, Ar). dC
(75 MHz, CDCl3) 33.6, 55.3, 105.4, 118.7, 119.3, 124.8, 126.3,
128.4, 132.0, 135.9, 136.3, 138.7, 142.0, 155.3, 159.1, 161.3.
n
max (KBr)/cmꢀ1 3090, 3035 1595, 1438, 1389, 1110, 824. Found
C 70.00, H 4.26, N 9.20. C18H13ClN2O requires C 70.02, H 4.24,
N 9.07 %.
3-(4-Fluorophenyl)-8-methoxy-5H-indeno[1,2-c]
pyridazine (15u)
3-(3,4-Dimethoxyphenyl)-6-chloro-5H-indeno[1,2-c]
pyridazine (15p)
Compound 15u was obtained as white needles, mp 205–
2078C. dH (300 MHz, CDCl3) 3.90 (s, 2H, CH2), 3.93 (s, 3H,
OCH3), 7.07 (dd, J1 6, J2 2.4, 1H, Ar), 7.20 (t, J 8.7, 2H, Ar), 7.46
(d, J 8.4, 1H, Ar), 7.82 (s, 1H, Ar), 7.87 (s, 1H, Ar), 8.04–8.18
(m, 2H, Ar). dC (75MHz, CDCl3) 33.9, 55.6, 105.0, 115.7, 116.0,
118.4, 119.7, 126.0, 128.9, 129.0, 133.1, 135.0, 138.9, 142.5,
155.5, 159.9, 161.6, 162.2, 162.3, 165.5. nmax (KBr)/cmꢀ1 3070,
3007, 2939, 2906, 2842, 1599, 1512, 1481, 1392, 1231, 1052, 846.
Found C 73.99, H 4.50, N 9.60. C18H13FN2O requires C 73.96,
H 4.48, N 9.58 %.
Compound 15p was obtained as white needles, mp
195–1978C. dH (300MHz, CDCl3) 3.94 (s, 6H, 2 ꢁ OCH3), 4.01
(s, 2H, CH2), 6.93 (d, J 8.4, 1H, Ar), 7.43–7.56 (m, 3H, Ar), 7.91
(d, J 7.2, 2H, Ar), 8.18–8.23 (m, 1H, Ar). dC (75 MHz, CDCl3)
34.2, 55.9, 56.0, 110.0, 111.0, 119.4, 120.0, 129.3, 129.6, 129.8,
131.4, 139.7, 140.6, 140.7, 149.5, 150.7, 156.3, 160.7, 162.3. nmax
(KBr)/cmꢀ1 3095, 3057, 3032, 2952, 2897, 1589, 1516, 1461,
1244, 1024, 793. Found C 67.38, H 4.49, N 8.40. C19H15ClN2O2
requires C 67.36, H 4.46, N 8.27 %.