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Organic & Biomolecular Chemistry
yield); m.p. 249–250 °C; IR (KBr): 3366, 2933, 1773, 1765, 1522, 122.1, 119.6, 119.4, 118.9, 113.9, 110.9, 70.3, 61.6, 21.4; HRMS
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1374, 1016 cm−1; H NMR (300 MHz; DMSO-d6): δH 7.98–7.96 (ESI-TOF) m/z: [M + H]+ calculated for C23H20N2O4: 389.15;
(m, 1H), 7.92–7.89 (m, 1H), 7.48 (d, J = 8.4 Hz, 1H), 7.31–7.24 found 389.149.
(m, 3H), 6.87–6.81 (m, 1H), 2.29 (s, 3H), 2.25 (s, 3H); 13C NMR
3-(1H-Benzo[d]imidazol-2-yl)pyridin-2-yl acetate (2l).
(75 MHz; DMSO-d6): δC 170.1, 152.9, 150.7, 146.3, 140.2, 129.9, Compound 2l was obtained as a brown solid (100 mg, 79%
129.9, 127.6, 126.8, 126.4, 116.8, 21.3; HRMS (ESI-TOF) m/z: yield); m.p. 134–136 °C; IR (KBr): 3360, 2936, 1775, 1765, 1621,
[M + H]+ calculated for C16H14N2O2: C 72.17; H 5.30; N 10.52; 1522, 1374 cm−1 1H NMR (600 MHz; DMSO-d6): δH 13.28 (s,
;
O 12.02%. Found: C 72.15; H 5.28; N 10.54%.
1H), 8.69–8.63 (m, 1H), 8.49–8.42 (m, 1H), 7.71–7.46 (m, 4H),
2-(1H-Benzo[d]imidazol-2-yl)-6-methylphenyl acetate (2g). 7.02–6.99 (m, 1H), 2.29 (s, 3H); 13C NMR (150 MHz; DMSO-d6):
Compound 2g was obtained as a white solid (108 mg, 81% δC 170.3, 151.4, 146.1, 144.0, 139.5, 139.4, 134.8, 132.8, 131.3,
yield); m.p. 155–157 °C; IR (KBr): 3366, 2935, 1771, 1766, 1524, 130.8, 130.3, 130.2, 128.9, 128.9, 128.6, 127.7, 127.5, 126.9,
1380, 1016, 665 cm−1 1H NMR (300 MHz; DMSO-d6): δH 125.6, 124.6, 124.5, 121.9, 119.3, 119.1, 118.9, 112.6, 112.2,
;
7.99–7.93 (m, 1H), 7.57 (d, J = 8.7 Hz, 1H), 7.43 (t, J = 7.7 Hz, 21.4; anal. calcd for C14H11N3O2: C 66.40; H 4.38; N 16.59; O
1H), 7.33–7.29 (m, 1H), 7.23–7.21 (m, 2H), 6.97–6.93 (m, 1H), 12.63%. Found: C 66.42; H 4.40; N 16.57%.
2.40 (s, 3H), 2.33 (s, 3H); 13C NMR (75 MHz; DMSO-d6): δC
5-Methyl-2-(quinazolin-2-yl)phenyl acetate (2m). Compound
170.1, 152.8, 146.3, 138.6, 131.0, 130.2, 129.2, 127.4, 123.9, 2m was obtained as a pale yellow solid (122.5 mg, 88% yield);
116.9, 21.4, 21.3; HRMS (ESI-TOF) m/z: [M + H]+ calculated for m.p. 228–230 °C; IR (KBr): 3360, 2942, 1626, 1776, 1761, 1522,
C16H14N2O2: C 72.17; H 5.30; N 10.52; O 12.02%. Found: C 1376 cm−1; 1H NMR (400 MHz; CDCl3): δH 9.57 (s, 1H), 8.63 (d,
72.16; H 5.28; N 10.53%.
J = 8.0 Hz, 1H), 8.12–8.02 (m, 4H), 7.79–7.72 (m, 1H), 7.38 (s,
2-(1H-Benzo[d]imidazol-2-yl)-5-cyanophenyl acetate (2h). 1H), 2.56 (s, 3H), 2.51 (s, 3H); 13C NMR (100 MHz; CDCl3): δC
Compound 2h was obtained as a white solid (112.3 mg, 81% 169.9, 160.9, 160.7, 154.8, 139.5, 135.3, 127.8, 127.6, 127.4,
yield); m.p. 254–256 °C; IR (KBr): 3366, 2933, 1773, 1765, 1522, 127.2, 119.3, 118.3, 28.4, 21.8; anal. calcd for C17H14N2O2: C
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1374, 1016, 667 cm−1; H NMR (300 MHz; DMSO-d6): δH 13.32 73.37; H 5.07; N 10.07; O 11.50%; found: C 73.35; H 5.06; N
(s, 1H), 8.36–8.34 (m, 2H), 8.07–8.04 (m, 2H), 7.71–7.61 (m, 10.09%.
1H), 7.39 (s, 1H), 7.04 (s, 1H), 2.32 (s, 3H); 13C NMR (75 MHz;
2-Nitro-6-(quinazolin-2-yl)phenyl acetate (2n). Compound 2n
DMSO-d6): δC 169.9, 150.2, 148.0, 140.2, 135.7, 127.5, 124.4, was obtained as a yellow solid (117.5 mg, 76% yield);
115.9, 20.9; anal. calcd for C16H11N3O2: C 69.31; H 4.00; N m.p. 250–252 °C; IR (KBr): 3189, 2982, 1768, 1628, 1522,
15.15; O 11.54%. Found: C 69.33; H 4.02; N 15.13%.
1016 cm−1; 1H NMR (300 MHz; CDCl3): δH 9.56 (s, 1H), 8.86 (d,
2-(1H-Benzo[d]imidazol-2-yl)-5-methoxyphenyl acetate (2i). J = 9.0 Hz, 1H), 8.09–8.04 (m, 3H), 7.92 (s, 1H), 7.85–7.74 (m,
Compound 2i was obtained as an off-white solid (115.7 mg, 2H), 2.46 (s, 3H); 13C NMR (75 MHz; CDCl3): δC 169.2, 161.2,
82% yield); m.p. 170–172 °C; IR (KBr): 3366, 2933, 1773, 1765, 155.1, 142.9, 138.9, 132.8, 128.9, 128.7, 127.4, 123.9, 21.1;
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1522, 1374, 1016, 667 cm−1; H NMR (300 MHz; DMSO-d6): δH HRMS (ESI-TOF) m/z: [M + H]+ calculated for (C16H11N3O4
8.15–8.12 (m, 1H), 7.95 (s, 1H), 7.66–7.57 (m, 2H), 7.34 (d, J = H)+: 310.082, found 195.1057.
7.2 Hz, 1H), 7.22–7.21 (m, 2H), 3.83 (s, 3H), 2.35 (s, 3H); 13C
+
NMR (75 MHz; DMSO-d6): δC 170.2, 160.0, 150.4, 131.3, 130.8,
Characterization data for the products (3a–f)
127.5, 123.2, 115.7, 112.0, 55.56, 21.32; HRMS (ESI-TOF) m/z:
[M + H]+ calculated for C16H14N2O3: C 68.08; H 5.00; N 9.92; O
17.00%. Found: C 68.10; H 5.02; N 9.90%.
2–2-([1,1′-Biphenyl]-2-yl)-1H-benzo[d]imidazole (3a). Compound
3a was obtained as a white solid (109.5 mg, 81% yield);
2-(1H-Benzo[d]imidazol-2-yl)-5-(methylthio)phenyl acetate (2j). m.p. 158–160 °C; IR (KBr): 3354, 2928, 1627, 1584, 1483, 1466,
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Compound 2j was obtained as a pale yellow solid (113.4 mg, 1372 cm−1; H NMR (400 MHz; DMSO-d6): δH 13.05 (brs, 1H),
76% yield); m.p. 225–227 °C; IR (KBr): 3356, 2934, 1776, 1511, 8.21–8.01 (m, 1H), 7.98–7.94 (m, 2H), 7.81–7.69 (m, 2H),
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1376, 1023, 705 cm−1; H NMR (300 MHz; DMSO-d6): δH 8.18 7.64–7.32 (m, 8H); 13C NMR (100 MHz; DMSO-d6): δC 145.6,
(d, J = 8.4 Hz, 1H), 7.66–7.62 (m, 3H), 7.26–7.23 (m, 2H), 5.64 140.8, 131.4, 130.8, 130.4, 130.1, 129.9, 129.2, 129.1, 129.0,
(s, 1H), 2.53 (s, 3H), 2.32 (s, 3H); 13C NMR (100 MHz; DMSO- 128.8, 128.5, 128.3, 128.1, 127.2, 127.1, 126.9, 126.5, 125.4,
d6): δc 171.2, 153.8, 152.8, 141.6, 135.2, 130.7, 127.2, 125.8, 124.8, 115.1; HRMS (ESI-TOF) m/z: [M + H]+ calculated for
112.3, 21.2, 14.3; HRMS (ESI-TOF) m/z: [M + H]+ calculated for C19H14N2: 271.12; found: 271.1203.
C16H14N2O2S: 299.08; found: 299.087.
2-(5-Methyl-[1,1′-biphenyl]-2-yl)-1H-benzo[d]imidazole (3b).
6-(1H-Benzo[d]imidazol-2-yl)-3-(benzyloxy)-2-methoxyphenyl Compound 3b was obtained as a white solid (115.2 mg, 81%
acetate (2k). Compound 2k was obtained as a white solid yield); m.p. 143–145 °C; IR (KBr): 3323, 2958, 1716, 1616 cm−1
;
(143.7 mg, 74% yield); m.p. 126–128 °C; IR (KBr): 3366, 2933, 1H NMR (400 MHz; DMSO-d6): δH 12.98 (s, 1H), 7.96–7.93 (m,
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1772, 1765, 1522, 1374, 1342, 1277, 1217, 1016 cm−1; H NMR 1H), 7.81 (s, 1H), 7.72 (m, 1H), 7.64–7.59 (m, 2H), 7.53–7.49
(600 MHz; DMSO-d6): 7.79–7.59 (m, 5H), 7.52–7.40 (m, 3H), (m, 1H), 7.48–7.27 (m, 6H), 2.50 (s, 3H); 13C NMR (100 MHz;
7.36–7.16 (m, 2H), 7.04 (s, 1H), 3.89 (s, 3H), 2.26 (s, 3H); 13C DMSO-d6): δC 155.0, 143.3, 140.8, 132.6, 130.8, 130.4, 129.3,
NMR (150 MHz; DMSO-d6): δ 166.9, 154.3, 149.5, 149.4, 147.5, 129.1, 129.1, 128.8, 128.5, 128.3, 128.1, 127.2, 127.1, 126.8,
144.2, 142.9, 137.4, 137.3, 136.4, 135.4, 131.2, 128.9, 128.9, 126.5, 125.4, 124.9; HRMS (ESI-TOF) m/z: [M + H]+ calculated
128.5, 128.4, 128.4, 128.3, 123.4, 123.2, 122.9, 122.7, 122.6, for C20H16N2: 285.14. Found: 285.143.
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