G
E. Łukasik, Z. Wróbel
Paper
Synthesis
HRMS (EI): m/z calcd for C14H835ClF3N2O: 312.0277; found: 312.0269.
IR (KBr): 3185, 1733, 1589, 1507, 1485 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 6.99–7.39 (m, 3 H), 7.55–7.83 (m, 2
H), 8.60–8.88 (m, 2 H), 11.49 (s, 1 H).
13C NMR (100 MHz, DMSO-d6): δ = 109.0, 110.6, 119.2, 122.4, 125.3,
127.7, 129.4, 141.7, 151.0, 152.6.
MS (EI): m/z (%) = 247 (39), 246 (18), 245 [M+] (100), 216 (18).
HRMS (EI): m/z calcd for C12H835ClN3O: 245.0356; found: 245.0359.
1-(2,4-Dimethoxyphenyl)-1,3-dihydro-2H-benzimidazol-2-one
(2n)13b
White solid; yield: 246 mg (91%); mp 210–213 °C.
IR (KBr): 3136, 3061, 1712, 1693, 1610, 1519 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 3.71 (s, 3 H), 3.84 (s, 3 H), 6.52 (d,
J = 7.6 Hz, 1 H), 6.65 (dd, J = 8.6, 2.2 Hz, 1 H), 6.78 (d, J = 2.2 Hz, 1 H),
6.89–6.95 (m, 1 H), 6.96–7.05 (m, 2 H), 7.26 (d, J = 8.6 Hz, 1 H), 10.93
(s, 1 H).
Acknowledgment
13C NMR (100 MHz, DMSO-d6): δ = 55.6, 55.7, 99.6, 105.3, 108.1,
This research was supported by the Polish National Centre of Science
(NCN), Research Grant UMO-2014/13/N/ST5/03423.
108.8, 115.2, 120.6, 121.1, 128.4, 130.5, 131.5, 153.7, 156.4, 160.7.
MS (EI): m/z (%) = 270 [M+] (100), 255 (21), 253 (22).
HRMS (EI): m/z calcd for C15H14N2O3: 270.1004; found: 270.1000.
Supporting Information
1-(3-Methoxyphenyl)-1,3-dihydro-2H-benzimidazol-2-one (2o)
Supporting information for this article is available online at
White solid; yield: 223 mg (93%); mp 136–139 °C.
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IR (KBr): 3010, 1701, 1603, 1582, 1497 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 3.80 (s, 3 H), 6.95–7.15 (m, 7 H),
7.43–7.52 (m, 1 H), 11.14 (s, 1 H).
13C NMR (100 MHz, DMSO-d6): δ = 55.4, 108.3, 109.1, 111.7, 113.1,
References
(1) (a) Łukasik, E.; Wróbel, Z. Synlett 2014, 25, 217. (b) Łukasik, E.;
Wróbel, Z. Synlett 2014, 25, 1987.
(2) Łukasik, E.; Wróbel, Z. Synthesis 2016, 48, 263.
(3) (a) Wróbel, Z.; Kwast, A. Synlett 2007, 1525. (b) Wróbel, Z.;
Kwast, A. Synthesis 2010, 3865. (c) Wróbel, Z.; Stachowska, K.;
Kwast, A. Synthesis 2013, 45, 127.
118.0, 120.9, 121.8, 128.4, 130.0, 130.1, 135.7, 153.1, 159.9.
MS (EI): m/z (%) = 240 [M+] (100), 198 (10), 181 (13).
HRMS (EI): m/z calcd for C14H12N2O2: 240.0899; found: 240.0908.
3-(2,6-Dimethylphenyl)-5-methoxy-1,3-dihydro-2H-imidazo[4,5-
h]quinolin-2-one (2p)
(4) Yu, B.; He, L.-N. ChemSusChem 2015, 8, 52.
(5) (a) Song, Q.-W.; Yu, B.; Li, X.-D.; Ma, R.; Diao, Z.-F.; Li, R.-G.; Li,
W.; He, L.-N. Green Chem. 2014, 16, 1633. (b) Reithofer, M. R.;
Sum, Y. N.; Zhang, Y. Green Chem. 2013, 15, 2086.
Yellow solid; yield: 284 mg (89%); mp >270 °C.
IR (KBr): 3000, 1694, 1633, 1597, 1523, 1489 cm–1
.
1H NMR (600 MHz, F3CCO2D): δ = 2.10 (s, 6 H), 4.08 (s, 3 H), 6.81 (s, 1
H), 7.40 (d, J = 7.8 Hz, 2 H), 7.52 (t, J = 7.8 Hz, 1 H), 7.90–8.00 (m, 1 H),
9.03 (d, J = 5.4 Hz, 1 H), 9.63 (d, J = 8.4 Hz, 1 H) (N–H proton was not
observed).
(6) (a) Tamura, M.; Noro, K.; Honda, M.; Nakagawa, Y.; Tomishige, K.
Green Chem. 2013, 15, 1567. (b) Tamura, M.; Noro, K.; Honda,
M.; Nakagawa, Y.; Tomishige, K. J. Chem. Technol. Biotechnol.
2014, 89, 19.
(7) (a) Zhao, Y.; Yu, B.; Yang, Z.; Zhang, H.; Hao, L.; Gao, X.; Liu, Z.
Angew. Chem. Int. Ed. 2014, 53, 5922. (b) Zheng, H.; Cao, X.; Du,
K.; Xu, J.; Zhang, P. Green Chem. 2014, 16, 3142. (c) Xiao, Y.;
Kong, X.; Xu, Z.; Cao, C.; Pang, G.; Shi, Y. RSC Adv. 2015, 5, 5032.
(8) Yu, B.; Zhang, H.; Zhao, Y.; Chen, S.; Xu, J.; Huang, C.; Liu, Z.
Green Chem. 2013, 15, 95.
13C NMR (150 MHz, F3CCO2D): δ = 18.2, 58.6, 95.1, 110.3, 120.5, 122.6,
127.4, 130.6, 131.8, 133.9, 138.5, 139.5, 145.4, 147.3, 157.4, 157.5.
MS (EI): m/z (%) = 319 [M+] (100), 304 (34), 276 (11), 262 (10).
HRMS (EI): m/z calcd for C19H17N3O2: 319.1312; found: 319.1324.
(9) Kimura, T.; Kamata, K.; Mizuno, N. Angew. Chem. Int. Ed. 2012,
51, 6700.
1-{2-[(4-Methylpiperazin-1-yl)methyl]phenyl}-1,3-dihydro-2H-
benzimidazol-2-one (2q)
(10) Yu, B.; Zhang, H.; Zhao, Y.; Chen, S.; Xu, J.; Hao, L.; Liu, Z. ACS
Catal. 2013, 3, 2076.
(11) Wright, J. B. Chem. Rev. 1951, 48, 397.
(12) (a) Li, Z.; Sun, H.; Jiang, H.; Liu, H. Org. Lett. 2008, 10, 3263.
(b) Massarotti, A.; Brunco, A.; Sorba, G.; Tron, G. C. J. Chem. Inf.
Model. 2014, 54, 396. (c) Benedi, C.; Bravo, F.; Uriz, P.;
Fernández, E.; Claver, C.; Castillón, S. Tetrahedron Lett. 2003, 44,
6073. (d) Barbero, N.; Carril, M.; SanMartin, R.; Dominguez, E.
Tetrahedron 2008, 64, 7283.
White solid; yield: 264 mg (82%); mp 163–166 °C.
IR (KBr): 3062, 2679, 1703, 1619, 1499 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 1.83–2.17 (m, 11 H), 3.23 (d, J =
12.0 Hz, 1 H), 3.45 (d, J = 12.0 Hz, 1 H), 6.54 (d, J = 8.0 Hz, 1 H), 6.92 (t,
J = 8.0 Hz, 1 H), 6.99–7.09 (m, 2 H), 7.34–7.57 (m, 4 H), 11.01 (s, 1 H).
13C NMR (100 MHz, DMSO-d6): δ = 45.6, 52.5, 54.3, 58.6, 107.8, 108.8,
120.5, 121.1, 128.0, 128.6, 128.7, 129.1, 130.5, 131.5, 133.3, 136.9,
153.4.
(13) (a) Chene, P.; Floersheimer, A.; Furet, P.; Shoepfer, J. WO
2006010594, 2006. (b) Bruncko, M.; Tahir, S. K.; Song, X.; Chen,
J.; Ding, H.; Huth, J. R.; Jin, S.; Judge, R. A.; Madar, D. J.; Park, C.-
P.; Park, C.-M.; Petros, A. M.; Tse, C.; Rosenberg, S. H.; Elmore, S.
W. Bioorg. Med. Chem. Lett. 2010, 20, 7503.
MS (EI): m/z (%) = 322 [M+] (60), 310 (33), 309 (19), 308 (100), 307
(35).
HRMS (EI): m/z calcd for C19H22N4O: 322.1794; found: 322.1809.
6-Chloro-1-pyridin-4-yl-1,3-dihydro-2H-benzimidazol-2-one (2r)
White solid; yield: 211 mg (86%); mp 270–272 °C.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–H