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ChemComm
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COMMUNICATION
Journal Name
imination/annulation/aza-allyl oxidation cascade sequence. For
inden-1-one tethered 3-oxyindole construction, the
intramolecular cyclization of o-alkynylaniline furnished the
cyclic C-acylimines. Then, these cyclic ketimines were subjected
to an alkylation reaction with the enol derived from the
dihydro-1H-inden-1-one derivative. The major features of our
methods are the external oxidant-free, additive-free and
distinguished ligand-free conditions, as well as the potential of
the greener oxidizing system FeCl3/DMSO.
Lett., 2017, 19, 1172-1175; (d) M. R. MDutOrIa: ,10G.1.0K3.9D/Ch9aCnCd0a3b3a7n5Ki,
J.-J. Wang, Adv. Synth. Catal., 2018, 360, 3960-3968; (e) S. S.
K. Boominathan, G. C. Senadi, J. K. Vandavasi, J. Y.-F. Chen and
J.-J. Wang, Chem. Eur. J., 2015, 21, 3193-3197; (f) G. C. Senadi
and J.-J. Wang, Green Chem., 2018, 20, 3420-3425.
8
9
(a) J.-F. Liu, Z.-Y. Jiang, R.-R. Wang, Y.-T. Zheng, J.-J. Chen, X.-
M. Zhang and Y.-B. Ma, Org. Lett., 2007, 9, 4127-4129; (b) A.
Karadeolian and M. A. Kerr, Angew. Chem., Int. Ed., 2010, 49,
1133–1135;
D. Bessinger, L. Ascherl, F. Auras and T. Bein, J. Am. Chem.
Soc., 2017, 139, 12035-12042; (b) C. L. Chochos, M. Spanos, A.
Katsouras, E. Tatsi, S. Drakopoulou, V. G. Gregoriou and A.
Avgeropoulos, Progress in Polymer Science, 2019, 91, 51-79.
Conflicts of interest
“Author claim no conflicts of interest”.
10 (a) Varun, Sonam and R. Kakkar, MedChemComm., 2019, DOI:
10.1039/C8MD00585K; (b) J. H. Lee, J.-H. So, J. H. Jeon, E. B.
Choi, Y.-R. Lee, Y.-T. Chang, C.-H. Kim, M. A. Bae and J. H. Ahn,
Chem. Commun., 2011, 47, 7500-7502.
11 a) K. Dhara, T. Mandal, J. Das, J. Dash, Angew. Chem., Int. Ed.
2015, 54, 15831-15835; (b) S. B. Jones, B. Simmons, D. W. C.
MacMillan, J. Am. Chem. Soc., 2009, 131, 13606–13607;
12 (a) Y.-J. Li, N. Yan, C.-H. Liu, Y. Yu, Y.-L. Zhao, Org. Lett., 2017,
19, 1160-1163; (b) W. Fu and Q. Song, Org. Lett., 2018, 20,
393-396;
13 (a) C. Felip-León, O. Martínez-Arroyo, S. Díaz-Oltra, J. F.
Miravet, N. Apostolova and F. Galindo, Bioorg. Med. Chem.
Lett., 2018, 28, 869-874; (b) N. Chufarova, K. Czarnecka, R.
Skibiński, M. Cuchra, I. Majsterek and P. Szymański, Arch.
Pharm. Chem. Life Sci., 2018, 351, 1800050-1800061; (c) Y. F.
Zheng, L. Parker, J. Driscoll, Z. Zhao, P. Donovan,
WO2018156925A1, Siemens Healthcare Diagnostics Inc.,
2018, pp. 83.
Acknowledgements
The authors gratefully acknowledge funding from the Ministry
of Science and Technology (MOST), Taiwan, and the Centre for
Research and Development of Kaohsiung Medical University for
400 MHz NMR analyses, LC-MS and GC-MS analysis. The authors
also thank to Dr. Siva Senthil Kumar Boominathan for technical
discussions.
Notes and references
1
(a) For selected reviews for phenanthroline (a) C. R. Luman
and F. N. Castellano, In Comprehensive Coordination
Chemistry II (ed.: J.M.McCleverty, T. J.Meyer), vol. 1:
Fundamentals: Ligands, Complexes, Synthesis, Purification,
and Structure (Ed.: A. B. P. Lever) Elsevier, 2008, pp. 25-43; (b)
G. Chelucci and R. P. Thummel, Chem. Rev. 2002, 102, 3129-
3170; (c) B.-H. Ye, M.-L. Tong and X.-M. Chen, Coord. Chem.
Rev., 2005, 249, 545-565.
14 (a) K. Matcha and A. P. Antonchick, Angew. Chem., Int. Ed.,
2013, 52, 2082–2086; (b) L. Guillemard, F. Colobert, J. Wencel-
Delord, Adv. Synth. Catal., 2018, 360, 4184-4190.
15 Y. Jahng, J. Hazelrigg, D. Kimball, E. Riesgo, F. Wu and R. P.
Thummel, Inorg. Chem., 1997, 36, 5390-5395; (b) F. Wu and
R. P. Thummel, Inorg. Chim. Acta, 2002, 327, 26-30.
16 (a) L. Jiang, F. Huang, Q. Wang, C. Sun, J. Liu and D. Chen, Org.
Chem. Front., 2018, 5, 2332-2339; (b) T. Patra, S. Manna and
D. Maiti, Angew. Chem., Int. Ed. 2011, 50, 12140-12142; (d) R.
J. Somerville and R. Martin, Angew. Chem., Int. Ed. 2017, 56,
6708–6710.
17 (a) R. Martínez, D. J. Ramón, M. Yus, J. Org. Chem., 2008, 73,
9778-9780; (b) C.-Y. Chen, W.-P. Hu, P.-C. Yan, G. C. Senadi
and J.-J. Wang, Org. Lett., 2013, 15, 6116-6119.
18 (a) X. Meng, Z. Fang, B.-D. Barry, P. Liao, X. Bi, Chin. Sci. Bull.,
2012, 57, 2361–2363; (b) V. Sridharan, P. Ribelles, M.T.
Ramos, J.C. Menéndez, J. Org. Chem., 2009, 74, 5715–5718;
(c) Y. Z. Hu, G. Zhang and R. P. Thummel, Org. Lett., 5, 2251-
2253; (d) K. K. Toh, Y.-F. Wang, E. P. J. Ng, S. Chiba, J. Am.
Chem. Soc., 2011, 133, 13942–13945;
19 (a) X. Chen, Y. Xie, C. Li, F. Xiao and G.-J. Deng, Eur. J. Org.
Chem., 2017, 577-581; (b) W.-L. Mu, M. Wang, H.-J. Li, D.-M.
Huang, Y.-Y. Zhang, C.-Y. Li, Y. Liu and Y.-C. Wu, Adv. Synth.
Catal., 2017, 359, 4250-4257;
20 (a) X. Zhang, P. Li, C. Lyu, W. Yong, J. Li, X. Pan, X. Zhu and W.
Rao, Adv. Synth. Catal., 2017, 359, 4147-4152; (b) W. Yong, P.
Li, R. Sheng, W. Rao and X. Zhang, ChemistrySelect, 2018, 3,
11696-11699.
2
3
(a) A. Bencini and V. Lippolis, Coord. Chem. Rev., 2010, 254,
2096-2180; (b) Z. Liu, L. Tian and S. Xi, Mater. Chem. & Phy,
2019, 222, 263-266;
(a) J.-B. Bongui, A. Elomri, d. Cahard, f. Tillequin, b. Pfeiffer, A.
Pierré and e. Seguin, Chem. Pharm. Bull., 2005, 53, 1540-1546;
(b) J. Durand and B. Milani, Coord. Chem. Rev., 2006, 250, 542-
560; (c) P. Alreja and N. Kaur, RSC Adv., 2016, 6, 23169-23218;
(d) A. P. Kulkarni, C. J. Tonzola, A. Babel and S. A. Jenekhe,
Chem. Mater., 2004, 16, 4556-4573; (e) A. P. Kulkarni, C. J.
Tonzola, A. Babel and S. A. Jenekhe Chem. Mater., 2004, 16,
4556-4573;
(a) M. Watanabe, H. Suzuki, Y. Tanaka, T. Ishida, T. Oshikawa
and A. Tori-i, J. Org. Chem., 2004, 69, 7794-7801; (b) D.
Hellwinkel and P. Ittemann, Liebigs Ann. Chem., 1985, 7, 1501-
1507; (c) K. J. Rajendra Prasad, Syn. Commun., 2017, 47, 990-
998.
4
5
6
S. A. Girard, H. Huang, F. Zhou, G.-J. Deng, C.-J. Li, Org. Chem.
Front., 2015, 2, 279-288; (b) U. Schuchardt, W. A. Carvalho, E.
V. Spinace, Synlett 1993, 10, 713.
(a) Y.-F. Liang, X. Li, X. Wang, M. Zou, C. Tang, Y. Liang, S. Song
and N. Jiao, J. Am. Chem. Soc., 2016, 138, 12271-12277; (b) M.
Xiong, Z. Gao, X. Liang, P. Cai, H. Zhu and Y. Pan, Chem.
Commun., 2018, 54, 9679-9682; (c) Z. Wang, X. Chen, H. Xie,
D. Wang, H. Huang and G.-J. Deng, Org. Lett., 2018, 20, 5470-
5473.
21 CCDC numbers: 3aa (1894798), 5aa (1894788), 7ab
(1902337), 5aa’ (1902433).
7
(a) G. C. Senadi, G. K. Dhandabani, W.-P. Hu and J.-J. Wang,
Green Chem., 2016, 18, 6241-6245; (b) G. K. Dhandabani, M.
R. Mutra, J.-J. Wang, Adv. Synth. Catal., 2018, 360, 4754-4763;
4 | J. Name., 2012, 00, 1-3
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