ACS Combinatorial Science
RESEARCH ARTICLE
2.60-2.69 (m, 2H), 4.18-4.40 (m, 2H), 6.99 (s, 1H), 7.19-7.35
(m, 6H), 7.40 (t, J = 7.3 Hz, 1H), 7.45 (s, 1H), 7.47-7.54 (m, 4H),
7.65-7.71 (m, 2H), 7.76 (d, J = 7.8 Hz, 1H); 13C NMR (100 MHz,
CDCl3) δ12.2, 13.7, 62.0, 62.9, 64.3, 69.3, 110.1, 119.9, 121.0, 122.5,
123.0, 125.9, 127.7, 127.8, 127.9, 128.7, 129.8, 130.6, 134.0, 135.6,
135.7, 136.8, 142.3, 142.6, 143.2, 166.5, 168.5; HRMS calcd for
C29H27N2O4 (Mþ þ H) 467.1971; found 467.1963.
164.5 (d, 1JCF = 249 Hz), 166.4, 168.8; HRMS calcd for C28H24-
FN2O4 (Mþ þ H) 471.1720; found 417.1718.
(Z)-Dimethyl 1-Benzylidene-5-fluoro-3-(1H-imidazol-1-yl)-
1H-indene-2,2(3H)-dicarboxylate 3{4,1}: yellow oil; 1H NMR (400
MHz, CDCl3) δ 2.89 (s, 3H), 3.70 (s, 3H), 6.54 (s, 1H), 6.62 (s,
1H), 6.93 (s, 1H), 7.00 (dd, J = 2.2, 8.0 Hz, 1H), 7.20-7.33 (m,
6H), 7.43 (d, J = 7.7 Hz, 2H), 7.67-7.70 (m, 1H); 13C NMR (100
MHz, CDCl3) δ 52.4, 53.5, 66.3, 69.7, 112.5 (d, 2JCF = 23.7 Hz),
118.3 (d, 2JCF = 23.7 Hz), 119.0, 122.4 (d, 3JCF = 9.16 Hz), 127.8,
127.9, 128.0, 128.6, 128.9, 134.1, 135.5, 137.3, 138.1, 138.8 (d,
3JCF = 8.40 Hz), 163.5 (d, 1JCF = 249 Hz), 166.6, 168.5; HRMS calcd
for C23H20FN2O4 (Mþ þ H) 407.1407; found 407.1401.
(Z)-Diethyl 3-(1H-Benzo[d]imidazol-1-yl)-1-benzylidene-
5-fluoro-1H-indene-2,2(3H)-dicarboxylate 3{4,3}: white solid; mp
150-151 °C; 1H NMR (400 MHz, CDCl3) δ 2.34 (s, 3H), 3.80 (s,
3H), 6.93 (s, 1H), 7.05 (dd, J = 2.2, 7.7 Hz, 1H), 7.18-7.33 (m,
7H), 7.36 (s, 1H), 7.39 (d, J = 7.7 Hz, 2H), 7.60 (d, J = 8.1 Hz, 1H),
7.71-7.75 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 51.9, 53.7,
63.9, 69.2, 109.7, 112.6 (d, 2JCF = 22.9 Hz), 118.5 (d, 2JCF = 22.9
Hz), 120.1, 122.6, 122.7, 123.2, 127.8, 128.0, 128.3, 128.4, 128.7,
133.7, 134.5, 135.4, 138.4, 138.5, 141.9, 143.1, 163.6 (d, 1JCF = 249.6
Hz), 166.3, 168.8; HRMS calcd for C27H22FN2O4 (Mþ þ H)
457.1564; found 457.1566.
(Z)-Diethyl 1-Benzylidene-3-(5-methyl-1H-benzo[d]imidazol-
1-yl)-1H-indene-2,2(3H)-dicarboxylate 3{2,4}: yellow oil; 1H NMR
(400 MHz, CDCl3) δ 0.19 (t, J = 7.1 Hz, 3H), 1.27 (t, J = 7.1 Hz,
3H), 2.47 (s, 3H), 2.63-2.72 (m, 2H), 4.18-4.39 (m, 2H), 6.94 (d,
J = 3.2 Hz, 1H), 7.05 (d, J = 7.3 Hz, 1H), 7.12 (d, J = 6.2 Hz, 1H),
7.19-7.21 (m, 1H), 7.24-7.28 (m, 1H), 7.32 (d, J = 7.7 Hz, 1H),
7.37-7.40 (m, 1H), 7.44 (s, 1H), 7.46-7.58 (m, 4H), 7.65-7.71
(m, 2H), 7.76 (d, J = 8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3)
δ 12.3, 13.7, 62.0, 62.9, 64.3, 69.3, 109.5, 119.4, 120.9, 124.0,
124.5, 125.8, 127.8, 127.9, 128.6, 128.7, 129.0, 129.8, 130.5, 132.1,
132.9, 135.7, 136.9, 141.8, 142.5, 166.4, 168.5; HRMS calcd for
C30H29N2O4 (Mþ þ H) 481.2127; found 481.2125.
(Z)-Diethyl 1-Benzylidene-3-(1H-naphtho[2,3-d]imidazol-
1-yl)-1H-indene-2,2(3H)-dicarboxylate 3{2,5}: white solid; mp
138-139 °C; 1H NMR (400 MHz, CDCl3) δ 0.18 (t, J = 7.3 Hz,
3H), 1.37 (t, J = 7.3 Hz, 2H), 2.61-2.70 (m, 2H), 4.30-4.50 (m,
2H), 7.17 (s, 1H), 7.23-7.27 (m, 1H), 7.30-7.35(m, 3H), 7.41-
7.50 (m, 5H), 7.54 (s, 1H), 7.56-7.62 (m, 3H), 7.86 ((d, J = 7.7
Hz, 1H), 8.01-8.07 (m, 2H), 8.13 (s, 1H), 8.26 (s, 1H); 13C
NMR (100 MHz, CDCl3) δ 12.3, 13.8, 62.1, 63.0, 64.5, 69.2,
105.9, 117.1, 121.1, 123.6, 124.5, 125.9, 127.6, 127.8, 127.9, 128.4,
128.7, 128.8, 129.9, 130.5, 130.6, 134.5, 135.6, 135.8, 136.9, 142.6,
146.1, 166.5, 168.6; HRMS calcd for C33H29N2O4 (Mþ þ H)
517.2127; found 517.2125.
(Z)-Dimethyl 1-Benzylidene-5-fluoro-3-(5-methyl-1H-benzo-
[d]imidazol-1-yl)-1H-indene-2,2(3H)-dicarboxylate 3{4,4}: yellow
oil; 1H NMR (400 MHz, CDCl3) δ 2.37 (s, 3H), 2.47 (s, 3H), 3.79
(s, 3H), 6.88(d, J= 3.7 Hz, 1H), 7.01-7.08 (m, 1H), 7.12-7.18 (m,
1H), 7.20-7.29 (m, 4H), 7.39-7.41 (m, 4H), 7.49(s, 1H), 7.58
(d, J = 8.4 Hz, 1H), 7.71-7.74 (m, 1H); 13C NMR (100 MHz,
CDCl3) δ21.4, 52.0, 53.7, 63.9, 69.2, 109.3, 112.6 (d, 2JCF =23.6Hz),
118.5 (d, 2JCF = 23.6 Hz), 119.6, 122.6 (d, 3JCF = 8.30 Hz), 124.2,
124.7, 127.8, 128.0, 128.3, 128.4, 128.8, 132.2, 133.3, 134.5, 135.4,
138.3 (d, 4JCF = 2.29 Hz), 138.7, 141.5, 141.8, 163.6 (d, 1JCF = 248.8
Hz), 166.4, 168.9; HRMS calcd for C28H24FN2O4 (Mþ þ H)
471.1720; found 471.1711.
(Z)-Dimethyl 3-Benzylidene-5-fluoro-1-(1H-imidazol-1-yl)-
1
1H-indene-2,2(3H)-dicarboxylate 3{3,1}: yellow oil; H NMR
(400 MHz, CDCl3) δ 2.87 (s, 3H), 3.72 (s, 3H), 6.52 (s, 1H),
6.61 (s, 1H), 6.91 (s, 1H), 7.00-7.10 (m, 1H), 7.23-7.38 (m, 7H),
7.43 (d, J= 8.0 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ52.4, 53.6,
(Z)-Dimethyl 1-Benzylidene-5-fluoro-3-(1H-naphtho[2,3-d]im-
idazol-1-yl)-1H-indene-2,2(3H)-dicarboxylate 3{4,5}: white solid;
2
66.2, 70.1, 107.6 (d, 2JCF = 23.7 Hz), 117.3 (d, JCF = 23.6 Hz),
119.1, 127.3 (d, 3JCF = 9.16 Hz), 128.2, 128.8, 128.9, 132.7, 134.4 (d,
mp 200-201 °C; H NMR (400 MHz, CDCl3) δ 2.29 (s, 3H),
1
3
4JCF = 3.0 Hz), 135.3, 137.3, 144.5 (d, JCF = 9.16 Hz), 164.4
3.82 (s, 3H), 7.04-7.09 (m, 2H), 7.20 (d, J = 7.7 Hz, 1H), 7.24-
7.28 (m, 3H), 7.34-7.46 (m, 6H), 7.74-7.77 (m, 1H), 7.95-8.00
(m, 3H), 8.21 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 52.1, 53.8,
(d, 1JCF = 248 Hz), 166.6, 168.4; HRMS calcd for C23H20FN2O4
(Mþ þ H) 407.1407; found 407.1396.
(Z)-Dimethyl 1-(1H-Benzo[d]imidazol-1-yl)-3-benzylidene-
5-fluoro-1H-indene-2,2(3H)-dicarboxylate 3{3,3}: yellow solid;
64.2, 69.1, 105.8, 112.6 (d, 2JCF = 21.9 Hz), 117.4, 118.6 (d, 2JCF
=
23.6 Hz), 122.7 (d, 3JCF = 8.39 Hz), 123.8, 124.7, 127.5, 127.9, 128.0,
128.4, 128.5, 130.3, 130.5, 134.5, 135.3, 138.3 (d, 4JCF = 2.29 Hz),
138.6, 145.6, 163.6 (d, 1JCF = 249.5 Hz), 166.4, 169.0; HRMS calcd
for C31H24FN2O4 (Mþ þ H) 507.1720; found 507.1718.
(Z)-Dimethyl 1-Benzylidene-3-(1H-imidazol-1-yl)-5,6-
dimethoxy-1H-indene-2,2(3H)-dicarboxylate 3{5,1}: white solid;
mp 166-167 °C; 1H NMR (400 MHz, CDCl3) δ 2.86 (s, 3H),
3.73 (s, 3H), 3.85 (s, 3H), 4.01 (s, 3H), 6.48 (s, 1H), 6.65 (s, 1H),
6.74 (s, 1H), 6.94 (s, 1H), 7.12(s, 1H), 7.20-7.24 (m, 2H),
7.28-7.32 (m, 3H), 7.43 (d, J = 7.3 Hz, 2H); 13C NMR (100
MHz, CDCl3) δ 53.3, 53.5, 56.5, 56.5, 66.9, 70.0, 102.4, 106.9,
125.7, 127.5, 128.0, 128.5, 129.3, 135.1, 135.5, 135.8, 151.3, 151.6,
167.0, 168.8; HRMS calcd for C25H25N2O6 (Mþ þ H) 449.1713;
found 449.1707.
1
mp 74-75 °C; H NMR (400 MHz, CDCl3) δ 2.37 (s, 3H),
3.81 (s, 3H), 6.92 (s, 1H), 7.10-7.13 (m, 1H), 7.19-7.33 (m, 7H),
7.37-7.43 (m, 4H), 7.61 (d, J = 8.0 Hz, 1H), 7.71 (d, J = 8.0 Hz,
1H); 13C NMR (100 MHz, CDCl3) δ 51.9, 53.7, 63.7, 69.5, 107.8
(d, 2JCF = 23.6 Hz), 109.9, 117.4 (d, 2JCF = 23.7 Hz), 120.0, 122.5,
123.1, 127.5, 127.5, 128.0, 128.1, 128.5, 128.7, 130.0, 132.2, 133.7,
134.8 (d, 4JCF = 3.0 Hz), 135.0, 141.9, 143.1, 144.8 (d, 3JCF = 8.4
1
Hz), 164.5 (d, JCF = 249 Hz), 166.3, 168.7; HRMS calcd for
C27H22FN2O4 (Mþ þ H) 457.1564; found 457.1564.
(Z)-Dimethyl 3-Benzylidene-5-fluoro-1-(5-methyl-1H-benzo-
[d]imidazol-1-yl)-1H indene-2,2(3H)-dicarboxylate 3{3,4}: yellow
oil; 1H NMR (400 MHz, CDCl3) δ 2.35 (s, 3H), 2.47 (s, 3H), 3.80
(s, 3H), 6.87 (d, J = 3.3 Hz, 1H), 7.05-7.14 (m, 3H), 7.22 (d, J =
7.7 Hz, 1H), 7.26-7.31 (m, 2H), 7.36-7.42 (m, 5H), 7.48 (d, J =
8.4 Hz, 1H), 7.57 (d, J= 8.4 Hz, 1H); 13CNMR(100MHz, CDCl3)
δ 21.5, 52.0, 53.7, 63.7, 69.4, 107.8 (d, 2JCF = 22.9 Hz), 109.7, 117.5
(d, 2JCF = 23.6 Hz), 119.5, 123.9, 124.2, 124.7, 127.5(d, 3JCF = 9.16
Hz), 128.0, 128.1, 128.6, 129.9, 132.3 (d, 3JCF = 7.0 Hz), 132.5, 133.2,
134.9 (d, 4JCF = 2.29 Hz), 135.1, 141.5, 144.8 (d, 3JCF = 8.40 Hz),
(Z)-Dimethyl 1-(1H-Benzo[d]imidazol-1-yl)-3-benzylidene-
5,6-dimethoxy-1H-indene-2,2(3H)-dicarboxylate 3{5,3}: white
1
solid; mp 240-241 °C; H NMR (400 MHz, CDCl3) δ 2.31
(s, 3H), 3.82 (s, 3H), 3.83 (s, 3H), 4.04 (s, 3H), 6.78 (s, 1H), 6.88
(s, 1H), 7.17-7.19 (m, 2H), 7.23-7.27 (m, 5H), 7.30 (d, J =
8.1 Hz, 1H), 7.39 (d, J = 7.3 Hz, 2H), 7.63 (d, J = 8.0 Hz, 1H), 7.71
16
dx.doi.org/10.1021/co100006g |ACS Comb. Sci. 2011, 13, 13–18