Lewis Acid Catalyzed C-N Bond Formation: Synthesis of Quinoxalines via CuX (X = Cl, Br, I) Catalyzed Cyclotrimerization of Alkynes with o-Phenylendiamines

Ying Liang; Pei-Zhen Liu; Chan-Cui Wu; Qian Zhang

doi:10.14233/ajchem.2015.18532

Issue

Vol. 27 No. 11 (2015): Vol 27 Issue 11

Issue Published : July 16, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Lewis Acid Catalyzed C-N Bond Formation: Synthesis of Quinoxalines via CuX (X = Cl, Br, I) Catalyzed Cyclotrimerization of Alkynes with o-Phenylendiamines

https://doi.org/10.14233/ajchem.2015.18532

Ying Liang

School of Life and Environmental Sciences, Guilin University of Electronic Technology, Guilin 541004, PR. China

Pei-Zhen Liu

Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004, P.R. China

Chan-Cui Wu

School of Life and Environmental Sciences, Guilin University of Electronic Technology, Guilin 541004, PR. China

Qian Zhang

School of Life and Environmental Sciences, Guilin University of Electronic Technology, Guilin 541004, PR. China

Corresponding Author(s) : Ying Liang

YingL@aliyun.com

Asian Journal of Chemistry, Vol. 27 No. 11 (2015): Vol 27 Issue 11
Article Published : July 16, 2015

Abstract

An efficient one-pot cycloisomerization reaction has been developed for the synthesis of quinoxaline derivatives from alkynes and o-phenylendiamines using CuX (X = Cl, Br, I) as a catalyst. This method provides a flexible and rapid route to synthesize quinoxaline derivatives.

Keywords

Alkynes o-Phenylendiamines Cycloisomerization CuX Quinoxaline derivatives

Liang, Y., Liu, P.-Z., Wu, C.-C., & Zhang, Q. (2015). Lewis Acid Catalyzed C-N Bond Formation: Synthesis of Quinoxalines via CuX (X = Cl, Br, I) Catalyzed Cyclotrimerization of Alkynes with o-Phenylendiamines. Asian Journal of Chemistry, 27(11), 3921–3924. https://doi.org/10.14233/ajchem.2015.18532

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P. Corona, A. Carta, M. Loriga, G. Vitale and G. Paglietti, Eur. J. Med. Chem., 44, 1579 (2009); doi:10.1016/j.ejmech.2008.07.025.

S. Paul and B. Basu, Tetrahedron Lett., 52, 6597 (2011); doi:10.1016/j.tetlet.2011.09.141.

A. Katoh, T. Yoshida and J. Ohkanda, Heterocycles, 52, 911 (2000); doi:10.3987/COM-99-S61.

K.R. Justin Thomas, M. Velusamy, J.T. Lin, C.-H. Chuen and Y.-T. Tao, Chem. Mater., 17, 1860 (2005); doi:10.1021/cm047705a.

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.

S. Ajaikumar and A. Pandurangan, Appl. Catal. A, 357, 184 (2009); doi:10.1016/j.apcata.2009.01.021.

D.K. Balta, S. Keskin, F. Karasu and N. Arsu, Prog. Org. Coat., 60, 207 (2007); doi:10.1016/j.porgcoat.2007.07.024.

J.Y. Lee, W.S. Shin, J.R. Haw and D.K. Moon, J. Mater. Chem., 19, 4938 (2009); doi:10.1039/b823536h.

L.J. Martin, A.L. Marzinzik, S.V. Ley and I.R. Baxendale, Org. Lett., 13, 320 (2011); doi:10.1021/ol1027927.

T. Mizuno, W.H. Wei, L.R. Eller and J.L. Sessler, J. Am. Chem. Soc., 124, 1134 (2002); doi:10.1021/ja017298t.

M. de Fatima Pereira and V. Thiéry, Org. Lett., 14, 4754 (2012); doi:10.1021/ol302006b.

J.J. Fu, H.S. Zang, Y. Wang, S.N. Li, T. Chen and X.D. Liu, Ind. Eng. Chem. Res., 51, 6377 (2012); doi:10.1021/ie202832e.

Y. Nagata, T. Nishikawa and M. Suginome, Chem. Commun., 11193 (2012); doi:10.1039/c2cc36275a.

S.Y. Kim, K.H. Park and Y.K. Chung, Chem. Commun., 1321 (2005); doi:10.1039/b417556e.

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.

J. Hou, Y.H. Liu and Z.H. Zhang, J. Heterocycl. Chem., 47, 703 (2010); doi:10.1002/jhet.388.

J.P. Wan, S.F. Gan, J.M. Wu and Y.J. Pan, Green Chem., 11, 1633 (2009); doi:10.1039/b914286j.

H.M. Bachhav, S.B. Bhagat and V.N. Telvekar, Tetrahedron Lett., 52, 5697 (2011); doi:10.1016/j.tetlet.2011.08.105.

M. Ayaz, J. Dietrich and C. Hulme, Tetrahedron Lett., 52, 4821 (2011); doi:10.1016/j.tetlet.2011.06.115.

W. Wang, Y.W. Shen, X. Meng, M.M. Zhao, Y.X. Chen and B.H. Chen, Org. Lett., 13, 4514 (2011); doi:10.1021/ol201664x.

L. Zhou, Y. Shi, Q. Xiao, Y.Z. Liu, F. Ye, Y. Zhang and J.B. Wang, Org. Lett., 13, 968 (2011); doi:10.1021/ol103009n.

T. Hamada, X. Ye and S.S. Stahl, J. Am. Chem. Soc., 130, 833 (2008); doi:10.1021/ja077406x.

Q. Xiao, Y. Xia, H. Li, Y. Zhang and J. Wang, Angew. Chem. Int. Ed., 50, 1114 (2011); doi:10.1002/anie.201005741.

Issue

Vol. 27 No. 11 (2015): Vol 27 Issue 11

Lewis Acid Catalyzed C-N Bond Formation: Synthesis of Quinoxalines via CuX (X = Cl, Br, I) Catalyzed Cyclotrimerization of Alkynes with o-Phenylendiamines

Corresponding Author(s) : Ying Liang

Abstract

Keywords

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