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Meng Tang et al.
2H), 6.48 (d, 1H, J=3.6 Hz), 6.64 (d, 1H, J=8.4 Hz), 6.89
(d, 1H, J=3.2 Hz), 7.06 (dd, 1H, J=8.4, 2.0 Hz), 7.24–7.32
(m, 2H), 7.38–7.42 (m, 2H), 8.09 (d, 1H, J=8.4 Hz);
13C NMR (100 MHz, CDCl3): d=49.7, 57.6, 108.2, 109.3,
109.7, 121.2, 121.67, 121.75, 127.3, 127.5, 129.2, 129.3, 132.9,
133.0, 134.1, 136.9, 140.7, 148.4, 154.1; HR-MS (ESI): m/z=
373.0510, calcd. for C19H15Cl2N2O2 [M+H]+: 373.0505.
Feliciano, Org. Lett. 2007, 9, 525–528; c) C. S. Cho,
D. K. Lim, N. H. Heo, T.-J. Kim, S. C. Shim, Chem.
Commun. 2004, 104–105.
[9] a) T. Zhang, W. Bao, J. Org. Chem. 2013, 78, 1317–
1322; b) X. Li, L. He, H. Chen, W. Wu, H. Jiang, J.
Org. Chem. 2013, 78, 3636–3646; c) K. Inamoto, T.
Saito, M. Katsuno, T. Sakamoto, K. Hiroya, Org. Lett.
2007, 9, 2931–2934.
[10] a) Q. Xiao, Y. Zhang, J. Wang, Acc. Chem. Res. 2013,
46, 236–247; b) Y. Zhang, J. Wang, Top. Curr. Chem.
2012, 327, 239–270; c) X. Zhao, Y. Zhang, J. Wang,
Chem. Commun. 2012, 48, 10162–10173; d) Z. Liu, J.
Wang, J. Org. Chem. 2013, 78, 10024–10030; e) Y. Xia,
Y. Zhang, J. Wang, ACS Catal. 2013, 3, 2586–2598.
[11] a) K. Inamoto, M. Katsuno, T. Yoshino, Y. Arai, K.
Hiroya, T. Sakamoto, Tetrahedron 2007, 63, 2695–2711;
b) K. Inamoto, M. Katsuno, T. Yoshino, I. Suzuki, K.
Hiroya, T. Sakamoto, Chem. Lett. 2004, 33, 1026–1027.
[12] T. Kylmälä, S. Udd, J. Tois, R. FranzØn, Tetrahedron
Lett. 2010, 51, 3613–3615.
Acknowledgements
The research was supported by the Fundamental Research
Funds for the Central Universities (lzujbky-2015-k12) and
partly supported by NSFC (No. 21002044). We acknowledge
Prof. Chun-An Fan and Prof. Shaohua Wang of Lanzhou
University for their helpful discussions.
References
[13] I. ThomØ, C. Besson, T. Kleine, C. Bolm, Angew.
Chem. 2013, 125, 7657–7661; Angew. Chem. Int. Ed.
2013, 52, 7509–7513.
[1] a) D. D. Gaikwad, A. D. Chapolikar, C. G. Devkate,
K. D. Warad, A. P. Tayade, R. P. Pawar, A. J. Domb,
Eur. J. Med. Chem. 2015, 90, 707–731; b) A. Thangadur-
ai, M. Minu, S. Wakode, S. Agrawal, B. Narasimhan,
Med. Chem. Res. 2012, 21, 1509–1523.
[14] J.-M. Lehn, Chem. Eur. J. 2006, 12, 5910–5915.
[15] L. Ratjen, J.-M. Lehn, RSC Adv. 2014, 4, 50554–50557.
[16] a) N. V. Kutsik-Savchenko, O. S. Lebed, A. V. Prosya-
nik, Comput. Theor. Chem. 2015, 1072, 15–20; b) M. E.
Belowich, J. F. Stoddart, Chem. Soc. Rev. 2012, 41,
2003–2024; c) M. N. Chaur, D. Collado, J.-M. Lehn,
Chem. Eur. J. 2011, 17, 248–258; d) S. He, Y. Tan, X.
Xiao, L. Zhu, Y. Guo, M. Li, A. Tian, X. Pu, N.-B.
Wong, J. Mol. Struc.: THEOCHEM 2010, 951, 7–13.
[17] a) A. Levina, A. Mitra, P. A. Lay, Metallomics 2009, 1,
458–470; b) K.-G. Lipponer, E. Vogel, B. K. Keppler,
Met.-Based Drugs 1996, 3, 243–260.
[18] a) N. C. Kallan, K. L. Spencer, J. F. Blake, R. Xu, J.
Heizer, J. R. Bencsik, I. S. Mitchell, S. L. Gloor, M.
Martinson, T. Risom, S. D. Gross, T. H. Morales, W.-I.
Wu, G. P. A. Vigers, B. J. Brandhuber, N. J. Skelton,
Bioorg. Med. Chem. Lett. 2011, 21, 2410–2414; b) A.
Vasudevan, A. J. Souers, J. C. Freeman, M. K. Verzal, J.
Gao, M. M. Mulhern, D. Wodka, J. K. Lynch, K. M.
Engstrom, S. H. Wagaw, S. Brodjian, B. Dayton, D. H.
Falls, E. Bush, M. Brune, R. D. Shapiro, K. C. Marsh,
L. E. Hernandez, C. A. Collins, P. R. Kym, Bioorg.
Med. Chem. Lett. 2005, 15, 5293–5297.
[19] a) S. M. Lynch, J. DeVicente, J. C. Hermann, S. Jaime-
Figueroa, S. Jin, A. Kuglstatter, H. Li, A. Lovey, J.
Menke, L. Niu, V. Patel, D. Roy, M. Soth, S. Steiner, P.
Tivitmahaisoon, M. D. Vu, C. Yee, Bioorg. Med. Chem.
Lett. 2013, 23, 2793–2800; b) M. Herdemann, I. Heit,
F.-U. Bosch, G. Quintini, C. Scheipers, A. Weber,
Bioorg. Med. Chem. Lett. 2010, 20, 6998–7003.
[20] a) S.-H. Kim, B. Markovitz, R. Trovato, B. R. Murphy,
H. Austin, A. Willardsen, J. V. Baichwal, S. Morham,
A. Bajji, Bioorg. Med. Chem. Lett. 2013, 23, 2888–2892;
b) R. Jiang, B. Frackowiak, Y. Shin, X. Song, W. Chen,
L. Lin, M. D. Cameron, D. R. Duckett, T. M. Kame-
necka, Bioorg. Med. Chem. Lett. 2013, 23, 2683–2687.
[21] M. Iwakubo, A. Takami, Y. Okada, T. Kawata, Y.
Tagami, H. Ohashi, M. Sato, T. Sugiyama, K. Fukushi-
ma, H. Iijima, Bioorg. Med. Chem. 2007, 15, 350–364.
[2] M. T. Gatto, B. Tita, M. Artico, L. Saso, Contraception
2002, 65, 277–278.
[3] a) L.-J. Huang, M.-L. Shih, H.-S. Chen, S.-L. Pan, C.-M.
Teng, F.-Y. Lee, S.-C. Kuo, Bioorg. Med. Chem. 2006,
14, 528–536; b) F.-Y. Lee, J.-C. Lien, L.-J. Huang, T.-M.
Huang, S.-C. Tsai, C.-M. Teng, C.-C. Wu, F.-C. Cheng,
S.-C. Kuo, J. Med. Chem. 2001, 44, 3746–3749.
[4] a) A. Veerareddy, G. Surendrareddy, P. K. Dubey,
Synth. Commun. 2013, 43, 2236–2241; b) C. Y. Cheng,
B. Silvestrini, J. Grima, M. Mo, L. Zhu, E. Johansson,
L. Saso, M.-G. Leone, M. Palmery, D. Mruk, Biol.
Reprod. 2001, 65, 449–461.
[5] a) Y. Cheng, W. Li, Y. Liu, H. C. Cheng, J. Ma, L. Qiu,
Chin. J. Cancer Res. 2012, 31, 248–256; b) S.-Y. Wu, S.-
L. Pan, T.-H. Chen, C.-H. Liao, D.-Y. Huang, J.-H.
Guh, Y.-L. Chang, S.-C. Kuo, F.-Y. Lee, C.-M. Teng, Br.
J. Pharmacol. 2008, 155, 505–513.
[6] a) B. P. Chekal, S. M. Guinness, B. M. Lillie, R. W.
McLaughlin, C. W. Palmer, R. J. Post, J. E. Sieser, R. A.
Singer, G. W. Sluggett, R. Vaidyanathan, G. J. With-
broe, Org. Process Res. Dev. 2014, 18, 266–274; b) E. J.
Flahive, B. L. Ewanicki, N. W. Sach, S. A. OꢀNeill-Sla-
wecki, N. S. Stankovic, S. Yu, S. M. Guinness, J. Dunn,
Org. Process Res. Dev. 2008, 12, 637–645.
ˇ
ˇ
ˇ
[7] a) N. Cankarovµ, J. Hlavµc, V. Krchnµk, Org. Prep.
Proced. Int. 2010, 42, 433–465; b) A. Schmidt, A. Beu-
tler, B. Snovydovych, Eur. J. Org. Chem. 2008, 4073–
4095; c) J. R. Hummel, J. A. Ellman, J. Am. Chem. Soc.
2015, 137, 490–498; d) Z. Liu, L. Wang, H. Tan, S.
Zhou, T. Fu, Y. Xia, Y. Zhang, J. Wang, Chem.
Commun. 2014, 50, 5061–5063; e) Y. Lian, R. G. Berg-
man, L. D. Lavis, J. A. Ellman, J. Am. Chem. Soc. 2013,
135, 7122–7125; f) D.-G. Yu, M. Suri, F. Glorius, J. Am.
Chem. Soc. 2013, 135, 8802–8805.
[8] a) X. Xiong, Y. Jiang, D. Ma, Org. Lett. 2012, 14, 2552–
2555; b) D. ViÇa, E. del Olmo, J. L. López-PØrez, A. S.
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Adv. Synth. Catal. 2016, 358, 926 – 939