Facile Regioselective Synthesis
Letters in Organic Chemistry, 2010, Vol. 7, No. 6
447
7.62 (1H, d, J = 6.9 Hz), 7.40-7.29 (2H, m), 7.10 (1H, d, J =
6.6 Hz), 6.99 (2H, d, J = 8.4 Hz), 6.11 (1H, bs, -NH). 13C
NMR (75 MHz, DMSO-d6):ꢀ198.0 (2C), 188.9, 163.6,
141.0 (2C), 137.7, 136.7 (2C), 136.3 (2C), 133.9, 133.8,
131.3, 130.8 (2C), 123.6 (2C), 119.5, 119.2, 98.9, 94.5, 61.8.
Anal. Calcd for C24H14INO3: C, 58.68; H, 2.87; N, 2.85.
Found: C, 58.61; H, 2.82; N, 2.80 %.
3-Amino-2-[2ꢀ-(2,4-dimethoxyphenyl)indanedionyl]inden-
one, 3i (remains as 4i in DMSO-d6)
Orange crystals; IR (KBr): 3403, 3312, 3237, 1706,
1
1620, 1537 cm-1. H NMR (300 MHz, DMSO-d6): ꢀ8.68
(1H, bs, -OH), 7.92-7.83 (4H, m), 7.65 (1H, d, J = 6.9 Hz),
7.37-7.31 (2H, m), 7.09 (1H, d, J = 6.9 Hz), 7.01 (1H, d, J =
8.1 Hz), 6.65 (1H, bs, -NH), 6.57-6.51 (2H, m), 3.73 (3H, s),
3.27 (3H, s). Anal. Calcd for C26H19NO5: C, 73.40; H, 4.50;
N, 3.29. Found: C, 73.35; H, 4.57; N, 3.25 %.
3-Amino-2-[2ꢀ-(4-methylphenyl)indanedionyl]indenone, 3f
(remains as 4f in DMSO-d6)
Orange crystals; IR (KBr): 3408, 3303, 3222, 1706,
3-Amino-2-[2ꢀ-(4-hydroxyphenyl)indanedionyl]indenone,
3j (remains as 4j in DMSO-d6)
1
1619, 1542 cm-1. H NMR (300 MHz, DMSO-d6): ꢀ8.21
(1H, bs, -OH), 8.00-7.90 (4H, m), 7.84-7.81 (2H, m), 7.58
(1H, d, J = 6.9 Hz), 7.40-7.28 (2H, m), 7.17-7.12 (3H, m),
5.42 (1H, bs, -NH), 2.25 (3H, s). Anal. Calcd for C25H17NO3:
C, 79.14; H, 4.52; N, 3.69. Found: C, 79.08; H, 4.47; N, 3.63
%.
Red crystals; IR (KBr): 3592, 3527, 3427, 3129, 1704,
1
1628, 1542 cm-1. H NMR (300 MHz, DMSO-d6): ꢀ9.68
(1H, s, phenolic-OH), 8.17 (1H, bs, -OH), 8.03-7.96 (4H, m),
7.60 (1H, d, J = 7.1 Hz), 7.44-7.32 (2H, m), 7.15-7.13 (3H,
m), 6.81 (2H, d, J = 8.7 Hz), 5.24 (1H, bs, -NH). 13C NMR
(75 MHz, DMSO-d6):ꢀ199.8 (2C), 190.2, 164.1, 157.8,
141.1 (2C), 138.8, 136.6 (2C), 133.9, 131.8, 131.1, 129.9
(2C), 123.9 (2C), 123.6, 119.8, 119.3, 116.5 (2C), 101.5,
61.6. Anal. Calcd for C24H15NO4: C, 75.58; H, 3.96; N, 3.67.
Found: C, 75.63; H, 3.91; N, 3.60 %.
3-Amino-2-[2ꢀ-(4-methoxyphenyl)indanedionyl]indenone,
3g
Orange-red crystals; IR (KBr): 3401, 3307, 3222, 1704,
1
1621, 1542 cm-1. H NMR (300 MHz, CDCl3): ꢀ8.07-8.04
(2H, m), 7.90-7.84 (2H, m), 7.46 (2H, d, J = 8.9 Hz), 7.33-
7.31(4H, m), 6.93 (2H, d, J = 8.9 Hz), 5.14 (2H, bs, -NH2),
3.80 (3H, s). 13C NMR (75 MHz, CDCl3):ꢀ 199.6 (2C),
191.0, 162.8, 159.5, 141.4 (2C), 138.2, 135.6 (2C), 133.4,
131.1, 130.7, 129.9 (2C), 128.8, 125.4, 123.8 (2C), 120.8,
116.4, 114.5 (2C), 61.1, 55.3. Anal. Calcd for C25H17NO4: C,
75.94; H, 4.33; N, 3.54. Found: C, 75.87; H, 4.29; N, 3.48
%.
3-Amino-2-[2ꢀ-(3-methyl-4-hydroxyphenyl)indanedionyl]
indenone, 3k (remains as 4k in DMSO-d6)
Orange-red crystals; IR (KBr): 3509, 3382, 3310, 3209,
1
1703, 1623, 1543 cm-1. H NMR (300 MHz, DMSO-d6):
ꢀ9.62 (1H, s, phenolic-OH), 8.15 (1H, bs, -OH), 8.00 (4H,
m), 7.59 (1H, d, J = 7.0 Hz), 7.44-7.32 (2H, m), 7.14 (1H, d,
J = 6.8 Hz), 7.02-6.96 (2H, m), 6.81 (1H, d, J = 8.3 Hz), 5.20
(1H, bs, -NH), 2.09 (3H, s). 13C NMR (75 MHz, DMSO-
d6):ꢀ199.9 (2C), 190.3, 164.1, 156.0, 141.1 (2C), 138.8,
136.6 (2C), 133.9, 132.0, 131.0, 129.2, 127.2, 125.3, 123.8
(2C), 123.3, 119.8, 119.3, 115.6, 101.5, 61.6, 19.3. Anal.
Calcd for C25H17NO4: C, 75.94; H, 4.33; N, 3.54. Found: C,
75.86; H, 4.28; N, 3.48 %.
3-Amino-2-[2ꢀ-(3,4-dimethoxyphenyl)indanedionyl]inden-
one, 3h
Orange crystals; IR (KBr): 3448, 3357, 1707, 1630, 1514
cm-1. 1H NMR (300 MHz, CDCl3): ꢀ7.94-7.89 (2H, m),
7.78-7.74 (2H, m), 7.21-7.17 (3H, m), 7.09 (1H, d, J = 2.1
Hz), 6.96-6.92 (2H, m), 6.76 (1H, d, J = 8.4 Hz), 5.08 (2H,
bs, -NH2), 3.78 (6H, s). 13C NMR (75 MHz, CDCl3):ꢀ199.6
(2C), 191.5, 163.0, 149.6, 149.2, 141.2 (2C), 138.3, 135.6
(2C), 133.3, 131.1, 130.7, 125.6, 123.8 (2C), 120.7, 120.6,
116.6, 111.9, 111.2, 103.5, 61.1, 56.1, 55.9. Anal. Calcd for
C26H19NO5: C, 73.40; H, 4.50; N, 3.29. Found: C, 73.34; H,
4.58; N, 3.24 %.
3-Amino-2-[2ꢀ-(3-methoxy-4-hydroxyphenyl)indanedionyl]
indenone, 3l (remains as 4l in DMSO-d6)
Orange crystals; IR (KBr): 3440, 3376, 3311, 3211,
1
1701, 1624, 1541 cm-1. H NMR (300 MHz, DMSO-d6): ꢀ
9.27 (1H, s, phenolic-OH), 8.09 (1H, bs, -OH), 7.99-7.93
(4H, m), 7.56 (1H, d, J = 6.9 Hz), 7.40-7.28 (2H, m), 7.09
(1H, d, J = 6.9 Hz), 6.84 (1H, d, J = 2.1 Hz), 6.76 (1H, d, J =
8.4 Hz), 6.64 (1H, dd, J = 8.4, 2.1 Hz), 5.17 (1H, bs, -NH),
3.65 (3H, s). Anal. Calcd for C25H17NO5: C, 72.99; H, 4.16;
N, 3.40. Found: C, 72.93; H, 4.12; N, 3.35 %.
3-Amino-2-[2ꢀ-(3,4-dimethoxyphenyl)indanedionyl]inden-
one, 3h (remains as 4h in DMSO-d6)
1H NMR (300 MHz, DMSO-d6): ꢀ8.14 (1H, bs, -OH),
8.00-7.90 (4H, m), 7.58 (1H, d, J = 6.9 Hz), 7.40-7.28 (2H,
m), 7.10 (1H, d, J = 6.9 Hz), 6.93 (1H, d, J = 8.4 Hz), 6.85
(1H, d, J = 2.1 Hz), 6.74 (1H, dd, J = 8.4, 2.1 Hz), 5.37 (1H,
bs, -NH), 3.70 (3H, s), 3.63 (3H, s). 13C NMR (75 MHz,
DMSO-d6):ꢀ199.2 (2C), 189.9, 163.8, 149.2, 149.0, 140.7
(2C), 138.4, 136.3 (2C), 133.6, 131.4, 130.7, 125.3, 123.6
(2C), 120.7, 119.5, 119.1, 112.2, 112.0, 100.8, 61.5, 55.7,
55.6.
3-Amino-2-[2ꢀ-(3-chloro-4-hydroxyphenyl)indanedionyl]
indenone, 3m (remains as 4m in DMSO-d6)
Red crystals; IR (KBr): 3373, 3221, 1702, 1623, 1542
cm-1. 1H NMR (300 MHz, DMSO-d6): ꢀ10.40 (1H, s,
phenolic-OH), 8.33 (1H, bs, -OH), 8.05-7.98 (4H, m), 7.67
(1H, d, J = 7.0 Hz), 7.45-7.33 (2H, m), 7.15-7.14 (2H, m),
7.05-6.97 (2H, m), 6.00 (1H, bs, -NH). 13C NMR (75 MHz,
DMSO-d6):ꢀ199.1 (2C), 189.6, 164.1, 153.4, 141.2 (2C),
138.4, 136.7 (2C), 134.1, 131.8, 131.2, 130.0, 128.7, 125.5,
124.0 (2C), 120.5, 119.9, 119.6, 117.5, 100.1, 61.4. Anal.
Calcd for C24H14ClNO4: C, 69.32; H, 3.39; N, 3.37. Found:
C, 69.26; H, 3.34; N, 3.31 %.
3-Amino-2-[2ꢀ-(3,4-dimethoxyphenyl)indanedionyl]inden-
one, 3h (remains as 4h in Acetone-d6)
1H NMR (300 MHz, Acetone-d6): ꢀ8.00-7.95 (5H, m),
7.50 (1H, d, J = 6.3 Hz), 7.42-7.31 (2H, m), 7.20 (1H, dd, J
= 6.3, 1.8 Hz), 7.13 (1H, d, J = 1.8 Hz), 6.97-6.93 (2H, m),
5.26 (1H, bs, -NH), 3.78 (3H, s), 3.75 (3H, s).