RSC Advances
Paper
6
4
7.3, 67.2; HRMS (Thermo Q Exactive) calcd for C25
H
17FeN
3
O
2
8 J. B. Zhuo, X. Q. Yan, X. X. Wang, L. L. Xie and Y. F. Yuan,
Chin. J. Org. Chem., 2015, 35, 1090.
9 J. B. Zhuo, Q. Wan, X. Q. Yan, L. L. Xie and Y. F. Yuan, Chem.
J. Chin. Univ., 2015, 36, 477.
48.0743, found 448.0730.
0
2
-(1 -Acetyl)ferroenyl-1H-phenanthro[9,10-d]imidazole (2c).
ꢂ
1
3
d
8
7
1
78 mg, brown solid, yield: 56.5%. Mp >236 C; H NMR (DMSO-
6
, 600 MHz): d 13.02 (s, 1H), 8.87 (d, J ¼ 8.3 Hz, 1H), 8.83 (d, J ¼ 10 L. L. Ma, T. H. Leng, K. Wang, C. Y. Wang, Y. J. Shen and
.3 Hz, 1H), 8.54 (d, J ¼ 7.9 Hz, 1H), 8.46 (d, J ¼ 7.9 Hz, 1H), W. H. Zhu, Tetrahedron, 2017, 73, 1306.
.78–7.73 (m, 1H), 7.73–7.68 (m, 1H), 7.66–7.59 (m, 2H), 5.25 (s, 11 S. Saha, A. Ghosh, P. Mahato, S. Mishra, S. K. Mishra,
1
3
H), 4.75 (s, 1H), 4.56 (s, 1H), 4.52 (s, 1H), 2.11 (s, 3H); C NMR
E. Suresh, S. Das and A. Das, Org. Lett., 2010, 12, 3406.
(
DMSO-d
6
, 151 MHz): d 201.2, 149.0, 137.3, 127.8, 127.6, 127.5, 12 M. Alfonso, A. Espinosa, A. T ´a rraga and P. Molina, Org. Lett.,
1
7
27.4, 127.3, 125.4, 125.3, 124.5, 124.1, 122.7, 122.4, 122.3, 80.8,
2011, 13, 2078.
7.5, 73.8, 73.7, 71.4, 71.0, 68.6, 27.7; HRMS (Thermo Q Exac- 13 M. Alfonso, A. T ´a rraga and P. Molina, Org. Lett., 2011, 13,
6432.
tive) calcd for C H FeN O 445.0998, found 445.0997.
2
7
20
2
0
2
-(1 -Acetyl)ferrocenyl-1H-(2-itrophenanthro)[9,10-d]imid- 14 J. C. Wang, Z. M. Chen, L. Qiao, Y. X. Li, X. L. Jiao and
ꢂ
azole (2d). 490 mg, brown red solid, yield: 66.7%. Mp >194 C;
Y. R. Jin, Chin. J. Synth. Chem., 2012, 20, 324.
1
H NMR (DMSO-d
6
, 600 MHz): d 13.29 (d, J ¼ 84.7 Hz, 1H), 9.37 15 X. F. Wu, P. Wu, J. Y. Li, J. Lu and J. C. Wang, Chin. J. Org.
(
(
1
4
d, J ¼ 120.7 Hz, 1H), 9.11 (s, 1H), 8.94 (d, J ¼ 24.3 Hz, 1H), 8.56
Chem., 2017, 37, 1412.
d, J ¼ 23.9 Hz, 1H), 8.34 (s, 1H), 7.86 (d, J ¼ 31.7 Hz, 1H), 7.72 (s, 16 J. C. Wang, X. F. Wu, X. L. Jiao and M. Wang, Chin. J. Synth.
H), 5.26 (d, J ¼ 32.7 Hz, 2H), 4.78 (s, 2H), 4.57 (d, J ¼ 34.2 Hz,
Chem., 2014, 22, 174.
1
3
H), 2.10 (d, J ¼ 4.5 Hz, 3H); C NMR (DMSO-d , 151 MHz): 17 N. Xie, K. Feng, B. Chen, L. Zhang, Z. H. Tong and L. Z. Wu,
6
d 200.8, 150.0, 149.9, 145.7, 145.6, 138.3, 136.5, 131.5, 131.4,
Imaging Sci. Photochem., 2011, 29, 45.
29.1, 128.5, 128.1, 127.1, 126.4, 126.4, 126.3, 126.0, 125.8, 18 A. Jaffe, A. S. Valdes and H. I. Karunadasa, Chem. Mater.,
25.7, 125.4, 125.0, 123.5, 122.2, 121.9, 118.2, 117.7, 117.2, 80.5, 2015, 27, 3568.
6.4, 73.4, 71.3, 70.7, 68.4, 68.4, 27.3; HRMS (Thermo Q Exac- 19 A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
1
1
7
tive) calcd for C27
H
19FeN
3
O
3
490.0849, found 490.0845.
20 C. Lee, W. Yang and R. G. Parr, Phys. Rev. B: Condens. Matter
Mater. Phys., 1988, 37, 785.
2
1 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria,
M. A. Rob, J. R. Cheeseman, J. A. Montgomery Jr,
T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam,
S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi,
G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji,
M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa,
M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai,
M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross,
V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts,
R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi,
C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma,
G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski,
S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas,
D. K. Malick, A. D. Rabuck, K. Raghavachari,
J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford,
J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko,
P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith,
M. A. Al-Laham, C. Y. Peng, A. Nanayakkara,
M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen,
M. W. Wong, C. Gonzalez and J. A. Pople, Gaussian 03,
Gaussian Inc., Wallingford, CT, 2003.
Conflicts of interest
There are no conicts to declare.
Acknowledgements
We gratefully acknowledge the nancial support by the Beijing
Natural Science Foundation (No. 2173060) and the General
Plan of Beijing Municipal Education Commission (No.
KM201710028007).
Notes and references
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3788 | RSC Adv., 2018, 8, 3782–3788
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