JOURNAL OF CHEMICAL RESEARCH 2013 619
under nitrogen over 15 min at room temperature. Upon completion
of the addition, the reaction was continued for 24 h. The product was
obtained as yellowish, viscous oil. 1H NMR(CDCl3,ꢀ500ꢀMHz):ꢀδꢀ0.97ꢀ
(t, 9H, J=7.17 Hz, CH3), 1.59 (m, 12H, CH2), 2.45 (m, 6H, CH2), 4.05 (d,
2H, J=10 Hz, CH2), 7.79 (s, 1H, OH); 31P NMR (CDCl3):ꢀδꢀ74.85.ꢀAnal.ꢀ
Calcd for C14H30BrO2P (341.26): C, 49.27; H, 8.86. Found: C, 48.96; H,
8.23%.
1H, CH), 6.63 (s, 2H, HAr), 6.80 (m, 3H, HAr), 7.22 (m, 5H, HAr), 7.47 (s,
2H, HAr), 8.26 (s, 2H, NH). 13CꢀNMRꢀ(DMSO,ꢀ100ꢀMHz):ꢀδꢀ14.9,ꢀ54.8,ꢀ
66.5, 111.6, 112.4, 114.3, 118.4, 121.7, 124.6, 125.0, 127.8, 128.4, 135.1,
135.4, 157.7. Anal. Calcd for C25H20Br2N2O2 (540.25): C, 55.58; H, 3.73; N,
5.19. Found: C, 55.73; H, 3.81; N, 5.17%.
We acknowledge partial support of this work by the Research
Affairs Office of Bu-Ali Sina University and Center of
Excellence in Development of Environmentally Friendly
Methods for Chemical Synthesis (CEDEFMCS), Hamedan,
Iran.
Synthesis of bis(indolyl)methanes; general procedure
Indole (2 mmol) was added to a mixture of the aldehyde (1 mmol) and
phosphonium bromide (0.07 g, 0.2 mmol, 20 mol%) in a mortar, and the
resulting mixture was ground at room temperature for the appropriate
time (Table 3). After completion of the reaction, as monitored by TLC,
H2O (3 mL) was added, stirred for 3 min and filtered. The solid residue
was recrystallised from EtOAc/petroleum ether (1:2) to give the pure
product.
Received 23 July 2013; accepted 6 August 2013
Paper 1301995 doi:10.3184/174751913X13787959859380
Published online: 7 October 2013
2-(di(1H-Indol-3-yl)methyl)-6-methoxyphenol (2k): Pink solid,
FT-IRꢀ(KBr)ꢀν/cm−1: 3412, 3254, 2957, 1615, 1477, 1272, 743. 1H NMR
(DMSO,ꢀ400ꢀMHz):ꢀδꢀ3.85ꢀ(t,ꢀ3H,ꢀCH3,), 5.83 (b, 1H, OH), 6.30 (s, 1H,
CH), 6.74 (s, 2H, HAr), 7.40 (m, 11H, HAr), 7.87 (s, 2H, NH). 13C NMR
(DMSO,ꢀ100ꢀMHz):ꢀδꢀ55.2,ꢀ56.3,ꢀ109.8,ꢀ111.0,ꢀ119.2,ꢀ120.6,ꢀ121.9,ꢀ124.5,ꢀ
125.9, 127.1, 130.1, 132.7, 136.7, 143.2, 145.6. Anal. Calcd for C24H20N2O2
(368.43): C, 78.24; H, 5.47; N, 7.60. Found: C, 78.35; H, 5.39; N, 7.51%.
4-(di(1H-Indol-3-yl)methyl)-2-ethoxyphenol (2m): Pink solid, FT-IR
References
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5
1
(KBr)ꢀν/cm−1: 3411, 3312, 2930, 1603, 1510, 1456, 1215, 744. H NMR
(DMSO,ꢀ400ꢀMHz):ꢀδꢀ1.35ꢀ(t,ꢀ3H,ꢀCH3), 4.08 (q, 2H, CH2), 5.34 (b, 1H,
OH), 5.48 (s, 1H, CH), 6.62 (s, 2H, HAr), 6.93 (m, 11H, HAr), 8.39 (s, 2H,
NH). 13CꢀNMRꢀ(DMSO,ꢀ100ꢀMHz):ꢀδꢀ14.8,ꢀ55.3,ꢀ65.1,ꢀ111.2,ꢀ112.3,ꢀ115.8,ꢀ
119.2, 119.9, 120.2, 120.6, 121.9, 124.5, 127.0, 136.7, 137.2, 147.1, 147.6.
Anal. Calcd for C25H22N2O2 (382.45): C, 78.51; H, 5.80; N, 7.32%. Found:
C, 78.77; H, 5.61; N, 7.47%.
6
7
8
R. Giernoth, Angew. Chem. Int. Ed., 2010, 49, 2834.
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3,3’-([1,1’-Biphenyl]-4-yl-methylene)bis(1H-indole) (2u): Pink solid,
FT-IRꢀ(KBr)ꢀν/cm−1: 3420, 2960, 1618, 1487, 1455, 1337, 745. 1H NMR
(DMSO,ꢀ400ꢀMHz):ꢀδꢀ5.93ꢀ(s,ꢀ1H,ꢀCH),ꢀ6.72ꢀ(s,ꢀ2H,ꢀHAr),ꢀ7.25ꢀ(m,ꢀ17H,ꢀ
HAr), 8.03 (s, 2H, NH). 13CꢀNMRꢀ(DMSO,ꢀ100ꢀMHz):ꢀδꢀ55.3,ꢀ111.2,ꢀ119.1,ꢀ
120.5, 121.8, 124.6, 125.7, 127.2, 127.5, 128.6, 136.7, 140.4, 143.2. Anal.
Calcd for C29H22N2 (398.50): C, 87.41; H, 5.56; N, 7.03. Found: C, 87.23;
H, 5.29; N, 7.21%.
9
H.J. Wadsworth, B. Shan, D. O’shea, J.M. Passsmore, W. J. Trigg and A.
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Venkateswarlu, Synth. Commun., 2003, 33, 3687.
3,3’-((4-Butoxyphenyl)methylene)bis(1H-indole) (2x). Pink solid, FT-
1
IRꢀ(KBr)ꢀν/cm−1: 3416, 2955, 1617, 1467, 1275, 749. H NMR (CDCl3,
500ꢀMHz):ꢀδꢀ0.99ꢀ(t,ꢀ3H,ꢀCH3), 1.55 (m, 4H, CH2), 3.96 (t, 2H, CH2), 5.70
(s, 1H, CH), 6.63 (s, 2H, HAr), 6.68 (d, 2H, HAr), 7.25 (m, 10H, HAr),
8.12 (s, 2H, NH). 13C NMR (CDCl3,ꢀ125ꢀMHz):ꢀδꢀ13.9,ꢀ19.3,ꢀ31.4,ꢀ39.0,ꢀ
67.7, 112.6, 112.7, 114.4, 119.4, 122.3, 124.7, 124.8, 128.7, 129.4, 135.1,
135.4, 157.7. Anal. Calcd for C27H26N2O (394.51): C, 82.20; H, 6.64; N,
7.10. Found: C, 82.34; H, 6.37; N, 7.15%.
3,3’-([1,1’-Biphenyl]-4-yl-methylene)bis(5-bromo-1H-indole)
(3a):
Pinkꢀsolid,ꢀFT-IRꢀ(KBr)ꢀν/cm−1: 3446, 2960, 1613, 1458, 1095, 796. H
NMRꢀ(DMSO,ꢀ400ꢀMHz):ꢀδꢀ5.79ꢀ(s,ꢀ1H,ꢀCH),ꢀ6.70ꢀ(s,ꢀ2H,ꢀHAr),ꢀ7.25ꢀ(m,ꢀ
15H, HAr), 8.19 (s, 2H, NH); 13CꢀNMRꢀ(DMSO,ꢀ100ꢀMHz):ꢀδꢀ54.7,ꢀ111.7,ꢀ
113.1, 119.8, 120.9, 123.5, 124.6, 125.7, 127.1, 127.4, 128.6, 136.3, 136.9,
141.4, 143.4. Anal. Calcd for C29H20Br2N2 (556.29): C, 62.61; H, 3.62; N,
5.04. Found: C, 62.49; H, 3.67; N, 5.09%.
1
3,3’-(Naphthalen-2-ylmethylene)bis(5-bromo-1H-indole) (3b). Pink
solid,ꢀFT-IRꢀ(KBr)ꢀν/cm−1: 3425, 2934, 1616, 1484, 1211, 765. 1H NMR
(DMSO,ꢀ400ꢀMHz):ꢀδꢀ5.92ꢀ(s,ꢀ1H,ꢀCH),ꢀ6.65ꢀ(s,ꢀ2H,ꢀHAr),ꢀ7.26ꢀ(m,ꢀ6H,ꢀ
HAr), 7.50 (m, 4H, HAr), 7.74 (m, 3H, HAr), 8.09 (s, 2H, NH). 13C NMR
(DMSO,ꢀ100ꢀMHz):ꢀδꢀ55.1,ꢀ111.5,ꢀ113.1,ꢀ119.7,ꢀ120.7,ꢀ121.6,ꢀ123.4,ꢀ124.5,ꢀ
125.3, 125.6, 126.3, 127.1, 127.4, 127.8, 132.5, 133.9, 136.4, 142.7. Anal.
Calcd for C27H18Br2N2 (530.25): C, 61.16; H, 3.42; N, 5.28. Found: C,
60.92; H, 3.54; N, 5.11%.
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Iranica, 2010, 17, 31.
4-(Bis(5-bromo-1H-indol-3-yl)methyl)-2-ethoxyphenol (3c): Pink
28 D. Redmore, Use of phosphonium compounds as corrosion inhibitors. US
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1
solid,ꢀFT-IRꢀ(KBr)ꢀν/cm−1: 3431, 3259, 2941, 1605, 1512, 1121, 749. H
NMRꢀ(DMSO,ꢀ400ꢀMHz):ꢀδꢀ1.30ꢀ(t,ꢀ3H,ꢀCH3), 3.70 (q, 2H, CH2), 5.65 (s,
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