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Catalyst-Free Synthesis of Quinoxalines
Corresponding Author(s) : Qingle Zeng
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
Quinoxalines are a class of important heterocycles, so to explore a facile and practical new synthetic method is always demanded. We have developed a new catalyst-free domino synthesis of quinoxalines from phenacyl halides and 1,2-diaminoarenes. Phenacyl chlorides with lower activities are first used in synthesis of quinoxalines and afford up to 97 % yield with our protocol. Our process with sodium bicarbonate as deacid reagent is catalyst-free, simple, greener and practical.
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References
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S. Saravanakumar, M.K. Kindermann, J. Heinicke and M. Kockerling, Chem. Commun., 640 (2006); doi:10.1039/b512884f; M.S. Kulkarni, A.S. Kumbhar, H. Mohan and B.S.M. Rao, Dalton Trans., 6185 (2009); doi:10.1039/b903446c.
S. Dailey, J.W. Feast, R.J. Peace, I.C. Sage, S. Till and E.L. Wood, J. Mater. Chem., 11, 2238 (2001); doi:10.1039/b104674h.
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N.P. Xekoukoulotakis, C.P. Hadjiantoniou-Maroulis and A.J. Maroulis, Tetrahedron Lett., 41, 10299 (2000); doi:10.1016/S0040-4039(00)01847-5.
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M. Lian, Q. Li, Y. Zhu, G. Yin and A. Wu, Tetrahedron, 68, 9598 (2012); doi:10.1016/j.tet.2012.09.056.
(a) B.C. Ranu, K. Chattopadhyay and R. Jana, Tetrahedron, 63, 155 (2007); doi:10.1016/j.tet.2006.10.035; (b) S. Adimurthy, S. Ghosh, P.U. Patoliya, G. Ramachandraiah, M. Agrawal, M.R. Gandhi, S.C. Upadhyay, P.K. Ghosh and B.C. Ranu, Green Chem., 10, 232 (2008); doi:10.1039/b713829f.
S.K. Singh, P. Gupta, S. Duggineni and B. Kundu, Synlett, 2147 (2003); doi:10.1055/s-2003-42065.
B. Das, K. Venkateswarlu, K. Suneel and A. Majhi, Tetrahedron Lett., 48, 5371 (2007); doi:10.1016/j.tetlet.2007.06.036.
H.M. Meshram, G. Santosh Kumar, P. Ramesh and B. Chennakesava Reddy, Tetrahedron Lett., 51, 2580 (2010); doi:10.1016/j.tetlet.2010.01.107.
S.B. Wadavrao, R.S. Ghogare and A.V. Narsaiah, Org. Commun., 6, 23 (2013).
S. Paul and B. Basu, Tetrahedron Lett., 52, 6597 (2011); doi:10.1016/j.tetlet.2011.09.141.
P. Ghosh and A. Mandal, Tetrahedron Lett., 53, 6483 (2012); doi:10.1016/j.tetlet.2012.09.045.
J.-F. Zhou, G.-X. Gong, L.-T. An, Y. Liu, F.-X. Zhu, Y.-L. Zhu and S.-J. Ji, Synlett, 3163 (2008); doi:10.1055/s-0028-1087280.
B. Madhav, S. Narayana Murthy, V. Prakash Reddy, K. Rama Rao and Y.V.D. Nageswar, Tetrahedron Lett., 50, 6025 (2009); doi:10.1016/j.tetlet.2009.08.033.
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(a) C. Dai, X.F. Sun, X.Z. Tu, L. Wu, D. Zhan and Q. Zeng, Chem. Commun., 48, 5367 (2012); doi:10.1039/c2cc30814b; (b) D. Zhan, T. Li, H. Wei, W. Weng, K. Ghandi and Q. Zeng, RSC Adv., 3, 9325 (2013); doi:10.1039/c3ra41370e; (c) D. Zhan, T. Li, X. Zhang, C. Dai, H. Wei, Y. Zhang and Q. Zeng, Synth. Commun., 43, 2493 (2013); doi:10.1080/00397911.2012.717669.
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