7.15 (dd, J = 2.8, 1.5 Hz, 1H), 7.14 (d, J = 8.2, 1.7 Hz, 1H),
6.33 (t, J = 3.2 Hz, 1H), 5.99 (dd, J = 3.2, 1.5 Hz, 1H), 4.55
(brs, NH), 4.42 (t, J = 5.5 Hz, 2H), 3.94 (s, 3H), 3.73 (t, J =
5.5 Hz, 2H), 3.25 (s, 3H), 1.76–1.66 (q, J = 6.4 Hz, 2H), 1.48
(s, 3H), 0.86 (t, J = 6.4 Hz, 3H); 13C NMR (75 MHz, CDCl3)
d 168.1, 156.3, 142.9, 139.6, 136.6, 133.8, 126.6, 126.2, 124.9,
124.6, 122.3, 119.7, 117.1, 114.7, 114.3, 111.0, 110.6, 104.1,
71.2, 59.5, 55.0, 52.5, 45.3, 35.3, 27.3, 9.2; MS (ESI): m/z 445
(MH+); HRMS (ESI) calcd for C26H29N4O3: m/z 445.2240.
Methyl 1-(2-methoxyethyl)-2-(4-methyl-50H-spiro[cyclohexane-
1,40-pyrrolo[1,2-a]quinoxalin]-70-yl)-1H-benzimidazole-5-carboxy-
1
late 10n. White solid; H NMR (300MHz, CDCl3) d 8.51 (d,
J = 1.0 Hz, 1H), 8.03 (dd, J = 8.5, 1.0 Hz, 1H), 7.50 (d, J =
8.5 Hz, 1H), 7.40 (d, J = 1.6 Hz, 1H), 7.39 (dd, J = 8.2 Hz,
1H), 7.22 (dd, J = 8.2, 1.6 Hz, 1H), 7.15 (dd, J = 2.8, 1.2 Hz,
1H), 6.35 (t, J = 3.3 Hz, 1H), 6.04 (dd, J = 3.3, 1.2 Hz, 1H),
4.76 (brs, NH), 4.50 (t, J = 5.3 Hz, 2H), 3.98 (s, 3H), 3.77 (t,
J = 5.3 Hz, 2H), 3.28 (s, 3H), 2.06–2.01 (m, 2H), 1.80–1.67 (m,
4H), 1.27–1.14 (m, 3H), 0.99 (d, J = 6.4 Hz, 3H); 13C NMR
(75 MHz, CDCl3) d 168.0, 156.0, 142.2, 142.0, 139.4, 136.0,
135.7, 127.4, 124.9, 124.8, 121.0, 120.3, 117.7, 114.8, 114.6,
111.1, 110.6, 102.8, 71.1, 59.5, 52.5, 45.5, 36.2, 32.0, 30.4, 23.1,
14.5; MS (ESI): m/z 485 (MH+); HRMS (ESI) calcd for:
C29H33N4O3: m/z 485.2553. Found 485.2552; IR (cmꢁ1, KBr):
3322, 2929, 1710, 1610, 1492.
Found 445.2242; IR (cmꢁ1
, KBr): 3245, 2962, 1712,
1610, 1496.
Methyl
1-(2-methoxyethyl)-2-[4-methyl-4-(propan-2-yl)-
4,5-dihydropyrrolo[1,2-a]quinoxalin-7-yl]-1H-benzimidazole-5-
1
carboxylate 10k. White solid; H NMR (300MHz, CDCl3) d
8.51 (d, J = 1.1 Hz, 1H), 8.04 (dd, J = 8.5, 1.1 Hz, 1H), 7.50
(d, J = 8.5 Hz, 1H), 7.38 (d, J = 8.2 Hz, 1H), 7.22 (d, J =
1.6 Hz, 1H), 7.18 (dd, J = 3.0, 1.5 Hz, 1H), 7.15 (dd, J = 8.2,
1.6 Hz, 1H), 6.35 (t, J = 3.4 Hz, 1H), 6.03 (dd, J = 3.4,
1.5 Hz, 1H), 4.45 (t, J = 5.5 Hz, 2H), 4.31(brs, NH), 3.97
(s, 3H), 3.77 (t, J = 5.5 Hz, 2H), 3.28 (s, 3H), 1.98 (sept,
J = 6.4 Hz, 1H), 1.52 (s, 3H), 0.91–0.85 (d, J = 6.4 Hz, 6H);
13C NMR (75 MHz, CDCl3) d 168.1, 156.2, 142.9, 139.6,
136.3, 133.3, 126.8, 126.3, 125.0, 124.6, 122.3, 119.6, 116.4,
114.6, 114.2, 110.9, 110.5, 105.3, 71.2, 59.5, 54.9, 52.5, 45.4,
35.3, 27.3, 9.2; MS (ESI): m/z 459 (MH+); HRMS (ESI) calcd
Methyl 1-[2-(cyclohex-1-en-1-yl)ethyl]-2-(4,4-dimethyl-4,5-
dihydropyrrolo[1,2-a]quinoxalin-7-yl)-1H-benzimidazole-5-
1
carboxylate 10o. White solid; H NMR (300MHz, CDCl3) d
8.50 (d, J = 1.1 Hz, 1H), 8.03 (dd, J = 8.5, 1.1 Hz, 1H), 7.40
(t, J = 7.7 Hz, 2H), 7.24 (d, J = 1.5 Hz, 1H), 7.16 (d, J = 3.2,
1.4 Hz, 1H), 7.09 (dd, J = 8.2, 1.5 Hz, 1H), 6.33 (t, J =
3.2 Hz, 1H), 6.03 (dd, J = 3.2, 1.4 Hz, 1H), 5.18 (m, 1H), 4.67
(brs, NH), 4.36 (t, J = 7.0 Hz, 2H), 3.96 (s, 3H), 2.36 (t, J =
7.0 Hz, 2H), 1.93–1.78 (m, 4H), 1.50 (s, 6H), 1.46–1.45 (m,
4H); 13C NMR (75 MHz, CDCl3) d 168.0, 155.8, 142.2, 139.0,
136.6, 135.3, 133.4, 126.8, 126.0, 125.1, 125.0, 124.6, 122.1,
119.4, 117.2, 114.8, 114.5, 111.1, 110.4, 102.9, 52.5, 51.9, 44.3,
38.2, 29.8, 28.6, 25.5, 22.9, 22.3; MS (ESI): m/z 481 (MH+);
HRMS (ESI) calcd for C30H33N4O2: m/z 481.2603. Found
481.2606; IR (cmꢁ1, KBr): 3340, 2929, 1700, 1606, 1498.
for C27H31N4O3: m/z 459.2396. Found 459.2394; IR (cmꢁ1
,
KBr): 3266, 2958, 1712, 1610, 1498.
Methyl 1-(2-methoxyethyl)-2-(50H-spiro[cyclopentane-1,40-
pyrrolo[1,2-a]quinoxalin]-70-yl)-1H-benzimidazole-5-carboxylate
10l. Off white solid; 1H NMR (300MHz, CDCl3) d 8.51 (d,
J = 1.1 Hz, 1H), 8.03 (dd, J = 8.5, 1.1 Hz, 1H), 7.49 (d,
J = 8.5 Hz, 1H), 7.40 (d, J = 8.2 Hz, 1H), 7.27 (d, J = 1.7 Hz,
1H), 7.21(dd, J = 8.2, 1.7 Hz, 1H), 7.18 (dd, J = 2.9, 1.4 Hz,
1H), 6.34 (t, J = 3.4 Hz 1H), 6.03 (dd, J = 3.4, 1.4 Hz, 1H),
4.45 (t, J = 5.5 Hz, 2H), 4.41(brs, NH), 3.96 (s, 3H), 3.76 (t,
J = 5.5 Hz, 2H), 3.27 (s, 3H), 2.12–2.01 (m, 2H), 1.93–81 (m,
6H); 13C NMR (75 MHz, CDCl3) d 168.1, 156.2, 142.9, 139.6,
136.6, 134.9, 127.4, 126.2, 125.0, 122.3, 120.3, 117.6, 114.9,
114.7, 114.2, 111.0, 110.5, 103.1, 71.2, 62.7, 59.5, 52.5, 45.4,
40.2, 23.9; MS (ESI): m/z 457 (MH+); HRMS (ESI) calcd for
C27H29N4O3: m/z 457.2240. Found 457.2237; IR (cmꢁ1, KBr):
Methyl 1-[2-(cyclohex-1-en-1-yl)ethyl]-2-(4-ethyl-4-methyl-
4,5-dihydropyrrolo[1,2-a]quinoxalin-7-yl)-1H-benzimidazole-5-
1
carboxylate 10p. White solid; H NMR (300MHz, CDCl3) d
8.51 (d, J = 1.0 Hz, 1H), 8.03 (dd, J = 8.5, 1.0 Hz, 1H), 7.42
(d, J = 8.5 Hz, 1H), 7.36 (d, J = 8.2 Hz, 1H), 7.28 (d, J =
1.5 Hz, 1H), 7.14 (dd, J = 2.8, 1.3 Hz, 1H), 7.09 (dd, J = 8.2,
1.5 Hz, 1H), 6.35 (t, J = 3.2 Hz, 1H), 6.02 (dd, J = 3.2,
1.3 Hz, 1H), 5.18 (m, 1H), 4.42 (t, J = 7.2 Hz, 2H), 4.28 (brs,
NH), 3.98 (s, 3H), 2.38 (t, J = 7.2 Hz, 2H), 1.84–1.66 (m, 6H),
1.54 (s, 3H), 1.46–1.44 (m, 4H), 0.91 (t, J = 7.3 Hz, 3H);
13C NMR (75 MHz, CDCl3) d 168.1, 155.9, 139.2, 136.6,
135.3, 133.8, 133.5, 126.5, 126.4, 125.1, 124.9, 124.5, 122.3,
119.1, 116.7, 114.7, 114.3, 111.0, 110.3, 104.1, 55.0, 52.5, 44.3,
38.2, 35.4, 28.6, 27.3, 25.5, 23.0, 22.3, 9.8; MS (ESI): m/z 495
(MH+); HRMS (ESI) calcd for: C31H35N4O2: m/z 495.2760.
3322, 2944, 1710, 1608, 1494 cmꢁ1
.
Methyl 1-(2-methoxyethyl)-2-(50H-spiro[cyclohexane-1,40-
pyrrolo[1,2-a]quinoxalin]-70-yl)-1H-benzimidazole-5-carboxylate
10m. White solid; 1H NMR (300MHz, CDCl3) d 8.50 (d,
J = 1.1 Hz, 1H), 8.03 (dd, J = 8.6, 1.1 Hz, 1H), 7.49 (d,
J = 8.6 Hz, 1H), 7.40 (d, J = 1.7 Hz, 1H), 7.38 (d, J = 8.2 Hz,
1H), 7.21 (dd, J = 8.2, 1.7 Hz, 1H), 7.15 (dd, J = 2.6, 1.4 Hz,
1H), 6.34 (t, J = 3.4 Hz, 1H), 6.08 (dd, J = 3.4, 1.4 Hz, 1H),
4.80 (brs, NH), 4.48 (t, J = 5.4 Hz, 2H), 3.98 (s, 3H), 3.77 (t,
J = 5.4 Hz, 2H), 3.28 (s, 3H), 1.96–1.92 (m, 3H), 1.82–1.70 (m,
5H), 1.60–1.53 (m, 2H); 13C NMR (75 MHz, CDCl3) d 168.0,
156.0, 142.9, 139.4, 135.9, 127.3, 125.2, 124.8, 122.1, 120.3,
120.3, 117.7, 114.8, 114.5, 114.2, 111.1, 110.6, 103.4, 71.2, 59.5,
53.1, 52.5, 45.5, 36.7, 32.0, 22.0; MS (ESI): m/z 471 (MH+);
HRMS (ESI) calcd for C28H31N4O3: m/z 471.2396. Found
471.2394; IR (cmꢁ1, KBr): 3322, 2929, 1710, 1610, 1495.
Found 495.2763; IR (cmꢁ1
, KBr): 3340, 2925, 1700,
1605, 1496.
Methyl 1-[2-(cyclohex-1-en-1-yl)ethyl]-2-(4-methyl-4-pentyl-
4,5-dihydropyrrolo[1,2-a]quinoxalin-7-yl)-1H-benzimidazole-
5-carboxylate 10q. White solid; 1H NMR (300MHz, CDCl3) d
8.50 (d, J = 1.1 Hz, 1H), 8.04 (dd, J = 8.5, 1.1 Hz, 1H), 7.41
(d, J = 8.5 Hz, 1H), 7.37 (d, J = 8.2 Hz, 1H), 7.22 (d, J =
1.2 Hz, 1H), 7.17 (d, J = 2.8, 1.1 Hz, 1H), 7.05 (dd, J = 8.2,
1.2 Hz, 1H), 6.34 (t, J = 3.2 Hz, 1H), 6.00 (dd, J = 3.2,
1.1 Hz, 1H), 5.19 (m, 1H), 4.39 (brs, NH), 4.42 (t, J = 7.5 Hz,
2H), 3.96 (s, 3H), 2.37 (t, J = 7.5 Hz, 2H), 1.84–1.78 (m, 4H),
c
1394 New J. Chem., 2011, 35, 1385–1396
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2011