Paper
NJC
10 H. Komatsu, T. Miki, D. Citterio, T. Kubota, Y. Shindo,
Y. Kitamura, K. Oka and K. Suzuki, J. Am. Chem. Soc., 2005,
127, 10798–10799.
11 N. Kaur and S. Kumar, Chem. Commun., 2007, 3069–3070.
12 M. Schmittel and H. W. Lin, Angew. Chem., Int. Ed., 2007, 46,
893–896.
2-(Pyridin-2-yl)-1H-naphtho[2,3-d]imidazole-4,9-dione (2e)
dH (300 MHz; DMSO-d6; Me4Si): 7.55–7.59 (m, 1H), 7.85–7.88
(m, 2H), 8.01–8.07 (m, 1H), 8.10–8.13 (m, 2H), 8.3 (d, 1H,
J = 8.1 Hz), 8.76 (d, 1H, J = 4.2 Hz), 14.62 (s, 1H).
LCMS (ESI-APCI) m/z: [M + H]+ calcd for C16H9N3O2H, 276.0,
found, 276.1.
13 C. Lee, D. H. Hong and J. I. Hong, Tetrahedron Lett., 2001,
42, 8665–8668.
2-(Thiophen-2-yl)-1H-naphtho[2,3-d]imidazole-4,9-dione (2f)
14 A. Satheshkumar and K. P. Elango, Dyes Pigm., 2013, 96,
364–371.
15 D. A. Jose, A. Singh, A. Das and B. Ganguly, Tetrahedron
Lett., 2007, 48, 3695–3698.
16 L. S. Evans, P. A. Gale, M. E. Light and R. Qyesada, Chem.
Commun., 2006, 965–967.
dH (300 MHz; DMSO-d6; Me4Si): 7.23–7.26 (m, 1H), 7.80–7.86
(m, 3H), 8.02 (d, 1H, J = 3.6 Hz), 8.08–8.11 (m, 2H), 14.94 (s, 1H).
LCMS (ESI-APCI) m/z: calcd for C15H8N2O2S (M À H)À, 280.0,
found, 278.9.
2-Isopropyl-1H-naphtho[2,3-d]imidazole-4,9-dione (2g)
17 T. Mizuno, W.-H. Wei, L. R. Eller and J. L. Sessler, J. Am.
Chem. Soc., 2002, 124, 1134–1135.
18 J. You, H. Jeong, H. Seo and S. Jeon, Sens. Actuators, B, 2010,
146, 160–164.
19 J. L. Sessler, D. Cho and V. Lynch, J. Am. Chem. Soc., 2006,
128, 16518–16519.
20 K. Chang, D. Moon, M. S. Lah and K.-s. Jeong, Angew. Chem.,
2005, 117, 8140–8143.
dH (300 MHz; DMSO-d6; Me4Si): 1.33 (d, 6H, J = 7.2 Hz),
3.06–3.20 (m, 1H), 7.81–7.84 (m, 2H), 8.05–8.08 (m, 2H), 13.70
(s, 1H).
dC (75 MHz; DMSO-d6; Me4Si): 22.0, 33.2, 125.2, 126.1, 126.3,
126.8, 130.7, 131.0, 133.3, 133.8, 135.5, 142.8, 177.3, 181.1.
LCMS (ESI-APCI) m/z: calcd for C14H12N2O2H (M + H)+, 241.0,
found, 241.0.
21 F. Zapata, A. Caballero, A. Espinosa, A. Tarrage and
P. Molina, J. Org. Chem., 2008, 73, 4034–4044.
22 X. Peng, Y. Wu, J. Fan, M. Tian and K. Han, J. Org. Chem.,
2005, 70, 10524–10531.
23 H. Miyaji, W. Sato and J. L. Sessler, Angew. Chem., Int. Ed.,
2000, 39, 1777–1780.
2-(Trifluoromethyl)-1H-naphtho[2,3-d]imidazole-4,9-dione (2h)
dH (300 MHz; DMSO-d6; Me4Si): 7.83–7.86 (m, 2H), 8.08–8.11
(m, 2H).
LCMS (ESI-APCI) m/z: calcd for C12H5F3N2O2 (M À H)À,
266.0, found, 265.0.
24 A. J. Evans, S. E. Mathews, A. R. Cowley and P. D. Beer,
Dalton Trans., 2003, 4644–4650.
Acknowledgements
25 Z. Lin, Y. Zhao, C. Duan, B. Zhanga and Z. Bai, Dalton
Trans., 2006, 3678–3684.
26 Q. Li, Y. Guo, J. Xu and S. Shao, J. Photochem. Photobiol., B,
2011, 103, 140–144.
The authors thank the Council of Scientific and Industrial
Research, New Delhi, for the financial assistance to carry out
this work [02(0118)/13/EMR II].
27 E. J. Cho, H. M. Yeo, B. J. Ryu, H. A. Jeong and K. C. Nam,
Bull. Korean Chem. Soc., 2006, 27, 1967–1968.
28 P. Anzenbacher, M. A. Palacios, K. Jursikova and
M. Marquez, Org. Lett., 2005, 7, 5027–5030.
29 G. J. Mohr, Chem. Commun., 2002, 2248.
30 S. Park, K.-H. Hong, J.-I. Hong and H.-J. Kim, Sens. Actuators,
B, 2012, 174, 140–144.
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c
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