B(HSO4)3 as an Efficient Catalyst for the Syntheses
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1-(4-Bromophenyl)-2, 2- di(1H-indol-3-yl)ethanone (3b)
o
1
Brown solid; mp 229-231 C. IR (νmax, cm-1): 3400, 1676, 1583, 1452, 1004; H NMR
(DMSO) (400 MHz): δ= 6.32(s,1H), 6.83(s,2H), 6.94 (t, J =7.2 Hz, 2H), 7.04 (t, J =7.2 Hz,
2H), 7.25(d, J = 8 Hz, 2H), 7.42 (d, 2H), 7.42 (d, J = 8.2 Hz, 2H), 7.86 (d, J = 8.2 Hz, 2H),
9.23(2H,NH). 13C NMR (DMSO): δ= 42.81, 111.99, 113.69, 119.11, 119.69, 122.19,
124.69, 126.93, 128.11, 130.71, 132.18, 136.1, 137.08, 197.9; Anal. Calcd for C24H17BrN2O
(429.31): C, 67.14; H, 3.99; N, 6.53%, Found: C, 67.02; H, 4.07; N, 6.63%.
1-(4-Nitrophenyl)-2, 2- di(1H-indol-3-yl)ethanone (3c)
o
1
Brown solid; mp 225-227 C. IR (νmax, cm-1): 3400, 1676, 1527, 1342; H NMR (DMSO)
(400 MHz): δ= 6.7(s,1H), 6.94 (t, J =7.2 Hz, 2H), 7.04 (t, J =7.2 Hz, 2H), 7.18(d, J= 2
Hz, 2H), 7.33(d, J= 8 Hz, 2H), 7.55(d, J = 8 Hz, 2H), 8.25 (d, J= 8.4 Hz, 2H), 8.35(d, J= 8.4
Hz, 2H), 10.94(2H,NH). 13C NMR (DMSO): δ= 42.85, 112.05, 112.53, 119.07, 121.59,
124.22, 125.11, 126.86, 136.83, 130.28, 136.83, 142.05, 150.09, 197.43.; Anal. Calcd for
C24H17N3O3 (395.41): C, 72.90; H, 4.33; N, 6=10.63%, Found: C, 73.02; H, 4.41; N,
10.69%.
1-(Phenyl)-2, 2- di(1H-indol-3-yl)ethanone (3d)
o
1
Brown solid; mp 205-206 C. IR (νmax, cm-1): 3390, 1675, 1453, 1339, 1006, H NMR
(DMSO) (400 MHz) : δ= 6.64(s,1H), 6.93 (t, J =7.2 Hz, 2H), 7.04 (t, J =7.2 Hz, 2H),
7.17(s,2H), 7.33(d, J = 7.6 Hz, 2H), 7.46(d, J = 7.6 Hz, 2H), 7.55 (d, J = 7.6 Hz, 3H),
8.16(d, J = 7.6 Hz, 2H), 10.91(2H,NH). 13C NMR (DMSO): δ = 42.13, 112, 113.29, 118.97,
119.45, 121.5, 124.8, 126.98, 129.01, 129.15, 133.33, 136.83, 137.07, 198.3; Anal. Calcd for
C24H18N2O (350.41): C, 82.26; H, 5.18; N, 7.99%, Found: C, 82.32; H, 5.13; N, 7.84%.
1-(4-Chlorophenyl)-2, 2- di(benzotriazol-1-yl)ethanone (3e)
o
1
Brown solid; mp 185-187 C, IR (νmax, cm-1): 1694, 1588, 1281, 1073; H NMR (DMSO)
(400 MHz) : δ = 7.41(1H), 7.42 (t, J =7.2 Hz, 2H), 7.59 ( 2H), 7.59(d, J = 8.4 Hz, 2H), 7.83
(d, J = 8 Hz, 2H), 8.01 (d, J = 8.4 Hz, 2H), 8.06 (d, J = 8 Hz, 2H). 13C NMR (DMSO):
δ = 81.81, 112.07, 119.79, 124.88, 128.34, 129.44, 131.29, 132.54, 132.84, 139.43, 145.94,
191.82; Anal. Calcd for C20H13ClN6O (388.81): C, 61.78; H, 3.37; N, 21.61%, Found: C,
61.89; H, 3.42; N, 21.67%.
1-(4-Bromophenyl)-2, 2- di(benzotriazol-1-yl)ethanone (3f)
o
1
Brown solid; mp 222-224 C. IR (νmax, cm-1): 1694, 1587, 1274, 1008; H NMR (DMSO)
(400 MHz) : δ= 7.38(1H), 7.38(t, J =7.2 Hz, 2H), 7.48(d, J = 8.2 Hz, 2H), 7.58 (t, J =7.2 Hz,
2H), 7.78 (d, J = 8 Hz, 2H), 7.84 (d, J = 8 Hz, 2H), 8.01 (d, J = 8 Hz, 2H). 13C NMR
(DMSO): δ= 82.35, 112.55, 120.25, 124.98, 128.05, 129.1, 131.15, 132.25, 132.54, 133.32,
146.2, 192.2; Anal. Calcd for C20H13BrN6O (433.26): C, 55.44; H, 3.02; N, 19.40%, Found:
C, 55.49; H, 3.07; N, 19.32%.
1-(4-Nitrophenyl)-2, 2- di(benzotriazol-1-yl)ethanone (3g)
o
1
Brown solid; mp 217-219 C. IR (νmax, cm-1): 1692, 1532, 1351; H NMR (DMSO) (400
MHz) : δ = 7.44(1H), 7.44 (t, J =7.2 Hz, 2H), 7.59 (t, J =7.2 Hz, 2H), 7.85(d, J = 8 Hz, 2H),
8.07 (d, J = 8 Hz, 2H), 8.23 (d, J = 8.4 Hz, 2H), 8.32 (d, J = 8.4 Hz, 2H). 13C NMR
(DMSO): δ = 82.38, 112.18, 119.77, 124.92, 127.62, 125.11, 130.65, 132.48, 139.8, 145.95,
151.12, 191.8; Anal. Calcd for C20H13N7O3 (399.36): C, 60.15; H, 3.28; N, 24.55%, Found:
C, 60.02; H, 3.32; N, 24.67%.