MAHMOODI ET AL.
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2.9 | 3,30-([2,4Dichlorophenyl]methylene)bis
(4-hydroxy-2H-chromen-2-one) 3g
Gray powder, yield: 64%, m.p 198–199ꢀC [m.p
190–195ꢀC].[44] IR (KBr, ν cm−1): 3,421 (OH), 1,658
(stretch, C=O), 1,612 (C=C, olefin), 1,561 (C=C-stretch,
Ar), 1,102 (C–O ether), and 761 (OOP, C–H).
2.15 | 3,30,300,300‘-(1,4-Phenylenebis
[methanetriyl])tetrakis(4-hydroxy-2H-
chromen-2-one) 3m
White powder, yield: 55%, m.p 288–296ꢀC. IR (KBr,
cm−1): 3,450 (OH), 1,658 (stretch, C=O), 1,621 (C=C, ole-
fin), 1,564 (C=C-stretch, Ar), 1,349 (C–O–C lacton), and
1
761 (OOP, C–H). H NMR (DMSO-d6, 400 MHz) δ: 7.89
(s, 4H, He), 7.58 (s, 4H, Hc), 7.33–731 (8H, Hb, Hd), 7.01 (s,
4H, Ha), 6.31(s, 2H, Hj), 5.24 (s, 4H, OH) ppm. 13C NMR
(DMSO-d6, 100 MHz) δ: 165.3, 165.1 (Ch, Ca), 152.5 (Cb),
137.1 (Ck), 132.59, 127.14 (Cl, Cd), 124.4, 124.3 (Ce, Cf),
117.6 (Cg), 116.5 (Cc), 104.7 (Ci), and 36.0 (Cj) ppm.
2.10 | 3,30-([3-Methoxyphenyl]methylene)bis
(4-hydroxy-2H-chromen-2-one) 3h
Cream powder, yield: 86%, m.p 243–248ꢀC [m.p
235–236ꢀC].[29] IR (KBr, ν cm−1): 3,448 (OH), 1,662
(stretch, C=O), 1,613 (C=C, olefin), 1,567 (C=C-stretch,
Ar), 1,349 (C–O–C lacton), 1,097 (C–O ether), and
763 (OOP, C–H).
2.16 | 3,30,300,300‘-(((Hexane-1,6-diylbis[oxy])bis
(4,1-phenylene))bis(methanetriyl))tetrakis
(4-hydroxy-2H-chromen-2-one) 3n
Pink solid, yield: 60%, m.p 185–191ꢀC. IR (KBr, cm−1): 3,416
(OH), 1,665 (stretch, C=O), 1,612 (C=C, olefin), 1,565, 1,507
(C=C- stretch, Ar), 1,250 (C-O-C lacton), and 761 (OOP, C-H).
1H NMR (DMSO-d6, 400 MHz) δ: 7.91 (s, 4H, Ho), 7.61 (s,
4H, Hm), 7.37 (s, 4H, Hn), 7.06 (s, 4H, Hf), 6.81 (s, 4H, He),
6.30 (s, 2H, Hh), 5.20 (s, 4H, OH), 3.95 (s, 4H, Hc), 1.73 (s, 4H,
Hb), and 1.48 (s, 4H, Ha) ppm. 13C NMR (DMSO-d6,
100 MHz) δ: 165.29 (Cj), 164.16 (Cq), 157.22 (Cd), 152.67
(Ck), 131.8 (Cg), 129.94 (Cf), 128.22 (Cm), 124.38, 124.21 (Cn,
Cl), 116.42 (Cp), 115.37 (Co), 114.48 (Ce), 104 (Cl), 67.69 (Cc),
35.72 (Ch), 29.24 (Cb), and 25.87 (Ca) ppm.
2.11 | 3,30-([2-Methoxyphenyl]methylene)bis
(4-hydroxy-2H-chromen-2-one) 3i
Cream powder, yield: 68%, m.p 201–206ꢀC [m.p
213–215ꢀC].[44] IR (KBr, ν cm−1): 3,443 (OH), 1,652
(stretch, C=O), 1,611 (C=C, olefin), 1,560 (C=C-stretch,
Ar), and 758 (OOP, C–H).
2.12 | 3,30-([4-Nitrophenyl]methylene)bis
(4-hydroxy-2H-chromen-2-one) 3j
Pink powder, yield: 82%, m.p 231–239ꢀC [m.p 232–234ꢀC].[21]
IR (KBr, ν cm−1): 3,444 (OH), 1,655 (stretch, C=O), 1,611
(C=C, olefin), 1,560, 1,516, 1,447, 1,344 (stretch, NO2), 1,101
(C–O ether), and 769 (OOP, C–H).
2.17 | 3,30,300,300‘-(((Pentane-1,5-diylbis[oxy])
bis(4,1-phenylene))bis(methanetriyl))tetrakis
(4-hydroxy-2H-chromen-2-one) 3o
Pink powder, yield, yield: 65%, m.p 177–189ꢀC. IR (KBr,
cm−1): 3,416 (OH), 1,664 (stretch, C=O), 1,607 (C=C, ole-
fin), 1,565, 1,532, 1,508 (C=C-stretch, Ar), 1,248 (C–O–C
lacton), and 762 (OOP, C–H). 1H NMR (DMSO-d6,
400 MHz) δ: 9.88 (s, 4H, OH), 7.87 (s, 4H, Ho), 7.57 (s, 4H,
Hm), 7.31 (s, 4H, Hn), 7.15 (s, 4H, Hf), 6.78 (s, 4H, He),
6.27 (s, 2H, Hh), 4.13 (s, 4H, Hc), 1.79 (s, 4H, Hb), and 1.58
(s, 2H, Ha) ppm. 13C NMR (DMSO-d6, 100 MHz) δ:
165.21,165.21 (Cj, Cq), 157.04 (Cd),152.78 (Ck), 131.96
(Cg), 129.95 (Cf), 128.18 (Cm),124.46 (Cn),123.88 (Cl),
116.25 (Cp),115.40 (Co), 114.36 (Ce), 104.56 (Ci),68.47
(Cc), 35.76 (Ch), 28.71 (Cb), and 22.68 (Ca) ppm.
2.13 | 3,30-([2,6Dichlorophenyl]methylene)bis
(4-hydroxy-2H-chromen-2-one) 3k
Pink powder, yield: 91%, m.p 193–198ꢀC [m.p
178–180ꢀC].[45] IR (KBr, ν cm−1): 3,447 (OH), 1,698 (stretch,
C=O), 1,609 (C=C, olefin), 1,556, 1,508, (C=C-stretch, Ar),
1,308, 1,279 (C–O–C lacton), and 743 (OOP, C–H).
2.14 | 3,30-([3-Bromophenyl]methylene)bis
(4-hydroxy-2H-chromen-2-one) 3l
Pink powder, yield: 66%, m.p 213–218ꢀC [m.p
225–228ꢀC].[44] IR (KBr, ν cm−1): 3,412 (OH), 1,658 (stretch,
C=O), 1,609 (C=C, olefin), 1,558 (C=C-stretch, Ar), 1,345
(C–O–C lacton), 1,099 (Br-Ar), and 761 (OOP, C–H).
2.18 | 3,30-(Phenylmethylene)bis(4-hydroxy-
2H-chromen-2-one) and 3,30-(phenylmethylene)
bis(1H-indole) (3a and 6)
IR (KBr, cm−1): 3,413 (NH), 1,658 (stretch, C=O), 1,610
(C=C, olefin), 1,562 (C=C-stretch, Ar), and 746 cm−1