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Pl eNa es we dJ oo u nr no at l ao df j Cu hs te mm i as tr rgy ins
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ARTICLE
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a host fluorescent material 5a by transformation of the cyano
group.
Friesen, Bioorg. Med. Chem. Lett., 2009, 19, 5837-5841.
DOI: 10.1039/C9NJ00776H
3
. (a) P. P. P. V. M. Doble, Med Chem Res., 2015, 24, 2213-2226;
(
b) B. Côté, L. Boulet, C. Brideau, D. Claveau, D. Ethier, R.
Experimental
Frenette, M. Gagnon, A. Giroux, J. Guay, S. Guiral, J. Mancini,
E. Martins, F. Massé, N. Méthot, D. Riendeau, J. Rubin, D. Xu,
H. Yu, Y. Ducharme, R. W. Friesen, Bioorg. Med. Chem. Lett.,
General Procedure for cyanation reaction
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007, 17, 6816-6820; (c) J. J. Lin, F. Y. Meng, X. H. Li, Chinese
J. Struct. Chem., 2015, 35, 41-48.
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A reaction vial (10 mL) was charged with substrate (0.4 mmol),
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. (a) D. Rambabu, P. R. K. Murthi, B. Dulla, M. R. Basaveswara,
M. Pal, Synth. Commun., 2013, 43, 3083-3092; (b) J. L. Pinder,
R. E. Davis, J. D. Charrier, Tetrahedron Lett., 2014, 55, 4853-
4855; (c) C. Zhang, L. Zhang, N. Jiao, Green Chem., 2012, 14,
3273-3276; (d) O. Ravi, A. Shaikh, A. Upare, K. K. Singarapu, S.
R. Bathula, J. Org. Chem., 2017, 82, 4422-4428.
Cu(OAc)
mmol), K
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(0.48 mol), 2-(4-methylpiperazin-1-yl)acetonitrile (0.6
PO (0.8 mmol) and N,N-dimethylformamide (6 mL).
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The reaction mixture was stirred at 130 °C for 6 h under open
system through a condensing tube. The reaction mixture was
cooled and poured into water (60 mL). The mixture was
extracted with ethyl acetate (3 × 20 mL). Organic layers were
. (a) M. Chaitanya, P. Anbarasan, J. Org. Chem., 2015, 80, 3695-
3700; (b) N. K. Mishra, T. Jeong, S. Sharma, Y. Shin, S. Han, J.
Park, J. S. Oh, J. H. Kwak, Y. H. Jung, I. S. Kim, Adv. Synth.
Catal., 2015, 357, 1293-1298;(c) W. Su, T.-J. Gong, B. Xiao, Y.
Fu, Chem. Commun., 2015, 51, 11848-11851; (d) M.
Chaitanya, P. Anbarasan, Org. Lett., 2015, 17, 3766-3769.
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combined and dried over Na SO , filtered and concentrated
under reduced pressure. The crude material was purified by
silica gel column chromatography to give the desired cyanated
product.
.
(a) S. Takemoto, E. Shibata, M. Nakajima, Y. Yumoto, M.
Shimamoto, H. Matsuzaka, J. Am. Chem. Soc., 2016, 138,
Preparation of 11H-benzo[4,5]imidazo[2,1-a]isoindol-11-one
1
4836-14839; (b) J. Hubrich, T. Himmler, L. Rodefeld, L.
(5a)
Ackermann, ACS Catal., 2015, 5, 4089-4093; (c) J. A. Leitch, H.
P. Cook, Y. Bhonoah, C. G. Frost, J. Org. Chem., 2016, 81,
A reaction vial (5 mL) was charged with 3a (0.4 mmol, 86.9 mg)
and 4N KOH solution (1 mL). The reaction mixture was stirred
under reflux for 12 h. The pH was adjusted to around acid by
progressively adding dilute hydrochloric acid. The mixture was
extracted with ethyl acetate (3 × 20 ml). Organic layers were
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0081-10087; (d) K. Raghuvanshi, D. Zell, K. Rauch, L.
Ackermann, ACS Catal., 2016, 6, 3172-3175; (e) J. A. Leitch, C.
L. McMullin, M. F. Mahon, Y. Bhonoah, C. G. Frost, ACS Catal.,
2017, 7, 2616-2623.
7
. (a) B. Gao, S. Liu, Y. Lan, H. Huang, Organometallics, 2016, 35,
1
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480-1487; (b) M. Chaitanya, P. Anbarasan, Org. Lett., 2015,
2 4
combined and dried over Na SO , filtered and concentrated
7, 3766-3769; (c) J. Hu, G. B. Li, C. C. Yuan, Z. B. Huang, D. Q.
under reduced pressure. The crude material was purified by
silica gel column chromatography to give 2-(1H-inden-2-
yl)benzoic acid (4a)(69.0mg, 73%).
Shi, Y. S. Zhao, Org. Lett., 2016, 18, 5998-6001;(d) W. Miura,
K. Hirano, M. Miura, Org. Lett., 2016, 18, 3742-3745; (e) S.
Han, J. Park, S. Kim, S. H. Lee, S. Sharma, N. K. Mishra, Y. H.
Jung, I. S. Kim, Org. Lett., 2016, 18, 4666-4669;
A reaction vial (1 mL) was charged with 4a (0.2 mmol, 47.3 mg) 8. (a) K. J. Xiao, L. Chu, G. Chen, J. Q. Yu, J. Am. Chem. Soc., 2016,
and Ac O (0.3 mL). The reaction mixture was stirred under
2
reflux for 5 min. cooled, treated with i-PrOH (3 mL), washed
with petroleum ether, and dried to afford yellow crystals 5a.
1
38, 7796-7800; (b) Q. L. Yang, Y. Q. Li, C. Ma, P. Fang, X. J.
Zhang, T. S. Mei, J. Am. Chem. Soc., 2017, 139, 3293-3298; (c)
K. S. L. Chan, H. Y. Fu, J. Q. Yu, J. Am. Chem. Soc., 2015, 137,
2
042−2046; (d) Y. F. Dang, X. Deng, J. D. Guo, C. Y. Song, W. P.
Hu, Z. X. Wang, J. Am. Chem. Soc., 2016, 138, 2712-2723; (e)
K. J. Xiao, L. Chu, G. Chen, J. Q. Yu, J. Am. Chem. Soc., 2016,
Conflicts of interest
There are no conflicts to declare.
1
38, 7796-7800.
9
. (a) R. B. Bedford, J. G. Bowen, C. ꢀꢁndeꢂ-ꢃꢄlveꢂ, J. Org.
Chem., 2017, 82, 1719-1725; (b) T. Y. Zhang, J. B. Lin, Q. Z. Li,
J. C. Kang, J. L. Pan, S. H. Hou, C. Chen, S. Y. Zhang, Org. Lett.,
2
017, 19, 1764-1767;(c) Q. J. Yang, P. Y. Choy, W. C. Fu, B.
Acknowledgements
We are grateful for financial support from the Research Project
of the Natural Science Foundation of Heilongjiang Province of
China (No. B2018012).
Fan, F. Y. Kwong, J. Org. Chem., 2015, 80, 11193-11199; (d) G.
P. Qin, X. N. Chen, L. Yang, H. Huang, ACS Catal., 2015, 5,
2
882-2885; (e) P. B. De, S. Pradhan, T. Punniyamurthy, J. Org.
Chem., 2017, 82, 3183-3191; (f) Z. L. Li, K. K. Sun and C. Cai,
Org. Chem. Front., 2018, 5, 1848-1853. (g) K. J. Makaravage,
X. Shao, A. F. Brooks, L. Yang, M. S. Sanford ,P. J. Scott, Org.
lett., 2018, 20, 1530-1533.
1
0. B. Venu, B. Vishali, G. Naresh, V. V. Kumar, M. Sudhakar, R.
Kishore, J. Beltramini, M. Konarova, A. Venugopal, Catal. Sci.
Technol., 2016, 6, 8055-8062.
Notes and references
1. (a) T. Zhang, L. Z. Huang, J. Wu, D. Lu, B. L. Ma, Z. T. Du,
Heterocycles, 2013, 87, 1545-1552;(b) B. H. Zhou, B. J. Li, W. 11. L. Ma, M. S. Placzek, J. M. Hooker, N. Vasdev, S. H. Liang,
Yi, X. Z. Bu, L. Ma, Bioorg. Med. Chem. Lett., 2013, 23, 3759-
Chem. Commun., 2017, 53, 6597-6600.
3
763.
12. (a) G. G. Pawar, A. Brahmanandan, M. Kapur, Org. Lett., 2016,
18, 448-451; (b) Y. Y. Ping, Q. P. Ding, Y. Y. Peng, ACS Catal.,
2016, 6, 5989-6005.
2
. (a) Y. C. C. Chen, J. Taiwan Inst. Chem. E., 2009, 40, 155-161;
(b) T. T. Chang, M. F. Sun, Y. H. Wong, S. C. Yang, H. Y. Chen,
F. J. Tsai, C. Y. C. Chen, J. Taiwan Inst. Chem. E., 2011, 42, 13. (a) S. Singhal, S. L. Jain, B. Sain, Chem. Commun., 2009, 17,
5
80-591; (c) A. Giroux, L. Boulet, C. Brideau, A. Chau, D.
2371-2372; (b) H. Q. Do, O. Daugulis, Org. Lett., 2010, 12,
Claveau, B. Côté, D. Ethier, R. Frenette, M. Gagnon, J. Guay, S.
Guiral, J. Mancini, E. Martins, F. Massé, N. Méthot, D.
2517-2519.
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