A convenient and efficient method for the synthesis of new…
2
-(4-morpholinobenzilidine)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one 8c Yel-
low solid; Yield 84 %; mp: 210–212 °C; FT-IR (KBr) m 2967, 2833, 1677, 1594,
-
1
1
1
J = 8 Hz, Morpholino-CH -2,-6), 3.81–3.83 (4H,t, J = 8 Hz, Morpholino-CH -3,-
504, 1223, 1301, cm
;
H NMR (400 MHz, CDCl ): d 3.21–3.23 (4H,t,
3
2
2
5
,), 3.83 (2H, s, inden-CH ), 3.89 (3H, s, O–CH ), 3.94 (3H, s, O–CH ), 6.86–6.88
2 3 3
(
methine-H), 7.51–7.53 (2H, d, J = 8.7 Hz, Ar–H), ppm; CNMR (100 MHz,
2H, d, J = 8.7 Hz, Ar–H), 6.92 (1H, s, Ar–H), 7.27 (1H, s, Ar–H), 7.47 (1H, s,
1
3
CDCl ): d 31.0, 46.7, 54.8, 55.0, 65.4, 103.6, 105.9, 113.4, 125.2, 130.1, 130.9,
3
131.0, 131.2, 143.3, 148.2, 150.3, 153.7, 191.9 ppm. Anal. Calcd. For C H NO :
22 23 4
C, 72.39; H, 6.36; N, 3.83; Found: C, 70.18; H, 6.14; N, 3.83 %.
2
-(4-piperidinobenzilidine)-5, 6-dimethoxy-2, 3-dihydro-1H-inden-1-one 8d Brown
solid; Yield 85 %; mp: 204–206 °C; FT-IR (KBr) m 2927, 2849, 1680, 1587, 1507,
-
1 1
1
CH -3, 4, 5), 3.29–3.31 (4H,t, J = 10.3 Hz, piperidino-CH-2, 6), 3.89 (2H, s, inden-
232, 1301 cm ; H NMR (400 MHz, CDCl ): d 1.62–1.68 (6H,m, piperidino-
3
2
CH ), 3.94 (3H, s, O–CH ), 3.97 (3H, s, O–CH ), 6.90–6.92 (2H, d, J = 8.8 Hz,
2
3
3
Ar–H), 6.96 (1H, s, Ar–H), 7.32 (1H, s, Ar–H), 7.53–7.55 (2H, d, J = 9.0 Hz, Ar–
3
1
H), 7.55 (1H, s, methine-H) ppm; CNMR (100 MHz, CDCl ): d 23.2, 24.4, 31.2,
3
4
8.0, 55.1, 55.1, 103.9, 105.7, 106.1, 113.0, 113.8, 124.0, 130.3, 130.5, 131.3,
32.0, 132.2, 143.4, 148.4, 151.0, 153.8, 192.3 ppm. Anal. Calcd. For C H NO :
1
C, 76.10; H, 6.95; N, 3.85; Found: C, 73.09; H, 6.73; N, 3.73 %.
2
3
25
3
2
8
1
-[4-(N-methylpiperazinobenzilidine)]-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one.
Brown solid; Yield 79 %; mp: 220–222 °C; FT-IR (KBr) m 2925, 2862, 1684,
e
-
1 1
610, 1510, 1312, 1127, 1093 cm ; H NMR (400 MHz, CDCl ): d 2.39 (3H, s,
3
CH ), 2.62–2.64 (4H,t, J = 8 Hz, piperazino-CH), 3.35–3.37 (4H, t, J = 8 Hz,
piperazino-CH),3.87 (2H, s, inden-CH ), 3.94 (3H, s, O–CH ), 3.98 (3H, s, O–CH ),
3
2
3
3
6
.86–6.88 (2H, d, J = 8.7 Hz, Ar–H), 6.92 (1H, s, Ar–H), 7.27 (1H, s, Ar–H), 7.47
1
3
1H, s, methine-H), 7.51–7.53 (2H, d, J = 8.7 Hz, Ar–H), ppm; CNMR
(
(
100 MHz, CDCl ): d 32.0, 46.7, 52.0, 54.8, 55.0, 57.0, 104.6, 105.9, 114.4,
3
1
Calcd. For C H N O : C, 73.07; H, 6.94; N, 7.41; Found: C, 70.84; H, 6.68; N,
24.2, 130.1, 130.9, 131.0, 132.2, 143.3, 149.2, 150.3, 152.7, 192.9 ppm. Anal.
2
3 26 2 3
7
.12 %.
2-(4-benzimidazolobenzilidine)-5, 6-dimethoxy-2, 3-dihydro-1H-inden-1-one. 8f Yel-
low solid; Yield 82 %; mp: 238–240 °C; FT-IR (KBr) m 3002, 2964, 1679, 1494,
-
1 1
1
O–CH ), 4.00 (3H, s, O–CH ), 4.00 (2H, s, inden-CH ), 6.99 (1H, s, Ar–H),
457, 1302, 1254, 1220, 1120 cm ; H NMR (400 MHz, CDCl ): d 3.94 (3H, s,
3
3
3
2
7
.33–7.38 (3H, m, Ar–H), 7.60 (1H, s, Ar–H), 7.59–7.61 (2H, d, J = 8.4 Hz, Ar–H),
.61 (1H, s, methine-H), 7.82–7.84 (2H, d, J = 8.4 Hz, Ar–H), 7.88–7.91 (1H,m,
7
1
3
Ar–H), 8.16 (1H,s, Ar–H) ppm; CNMR (100 MHz, CDCl ): d 31.0, 55.1, 55.2,
3
1
03.9, 106.0, 109.4, 119.7, 122.0, 122.8, 129.5, 129.8, 130.9, 132.2, 134.1, 135.3,
35.6, 140.9, 143.1, 143.6, 148.6, 154.5, 191.7 ppm. Anal. Calcd. For C H N O :
1
C, 75.82; H, 5.10; N, 7.07; Found: C, 72.96.24; H, 4.92; N, 6.83 %.
2
5 20 2 3
2
-(4-pyrazolobenzilidine)-5, 6 dimethoxy-2, 3-dihydro-1H-inden-1-one 8g Yel-
low solid; Yield 81 %; mp: 220–222 °C; FT-IR (KBr) m 3115, 2926, 1685, 1598,
123