A Novel Synthesis of Carboxylic Acid Oxime Esters Catalyzed by 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium Tetrafluoroborate

Wei Shi; Jiming Zhang; Qin Zhou; Xingjian Wang; Xiaowei Qi; Lianyong Guo; Wanyong Ma; Jianhua Zhou

doi:10.14233/ajchem.2014.16522

Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

Issue Published : September 30, 2014

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

A Novel Synthesis of Carboxylic Acid Oxime Esters Catalyzed by 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium Tetrafluoroborate

https://doi.org/10.14233/ajchem.2014.16522

Wei Shi

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Jiming Zhang

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Qin Zhou

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Xingjian Wang

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Xiaowei Qi

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Lianyong Guo

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Wanyong Ma

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Jianhua Zhou

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Corresponding Author(s) : Jiming Zhang

zhangjiming@gmail.com; slzshiwei@163.com

Asian Journal of Chemistry, Vol. 26 No. 21 (2014): Vol 26 Issue 21
Article Published : September 30, 2014

Abstract

We describe a facile synthesis of carboxylic acid oxime esters in acetonitrile from the corresponding carboxylic acids and oximes catalyzed by 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate in the presence of triethylamine at room temperature under mild conditions.

Keywords

Oxime ester Carboxylic acid 2-(1H-Benzotriazole-1-yl)-1,1,3,3- tetramethyluronium tetrafluoroborate Oxime esterification

Shi, W., Zhang, J., Zhou, Q., Wang, X., Qi, X., Guo, L., … Zhou, J. (2014). A Novel Synthesis of Carboxylic Acid Oxime Esters Catalyzed by 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium Tetrafluoroborate. Asian Journal of Chemistry, 26(21), 7125–7128. https://doi.org/10.14233/ajchem.2014.16522

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References

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References

A. Karakurt, M.A. Alagoz, B. Sayoglu, U. Calis and S. Dalkara, Eur. J. Med. Chem., 57, 275 (2012); doi:10.1016/j.ejmech.2012.08.037.

G. Surkau, K.J. Böhm, K. Müller and H. Prinz, Eur. J. Med. Chem., 45, 3354 (2010); doi:10.1016/j.ejmech.2010.04.019.

Y.J. Cui, X.P. Rao, S.B. Shang, S. Jie and Y.Q. Gao, Lett. Drug Des. Discov., 10, 102 (2013); doi:10.2174/157018013804725071.

H.Q. Zhao, M.J. Zhou, L.F. Duan, W. Wang, J.J. Zhang, D.Q. Wang and X.M. Liang, Molecules, 18, 3615 (2013); doi:10.3390/molecules18033615.

C.D. Magnusson and G.G. Haraldsson, Chem. Phys. Lipids, 165, 712 (2012); doi:10.1016/j.chemphyslip.2012.07.005.

R. Sun, Y. Li, M. Lü, L. Xiong and Q. Wang, Bioorg. Med. Chem. Lett., 20, 4693 (2010); doi:10.1016/j.bmcl.2010.04.144.

N.J. Turro, Y.J. Li, S. Jockusch, Y. Hagiwara, M. Okazaki, R.A. Mesch, D.I. Schuster and C.G. Willson, J. Org. Chem., 78, 1735 (2013); doi:10.1021/jo302149u.

J. Xu, G.L. Ma, K.M. Wang, J.M. Gu, S. Jiang and J. Nie, J. Appl. Polym. Sci., 123, 725 (2012); doi:10.1002/app.34551.

S.S.P. Chou, J.C. Juan, S.C. Tsay, K.P. Huang and J.R. Hwu, Molecules, 17, 3370 (2012); doi:10.3390/molecules17033370.

C. Dworak and R. Liska, J. Polym. Sci. A, 48, 5865 (2010); doi:10.1002/pola.24396.

S.B. Liu, Y. Yu and L.S. Liebeskind, Org. Lett., 9, 1947 (2007); doi:10.1021/ol070561w.

D.J. Ritson, R.J. Cox and J. Berge, Org. Biomol. Chem., 2, 1921 (2004); doi:10.1039/b402764g.

S.K. Kundu, M. Rahman, P. Dhara, A. Hajra and A. Majee, Synth. Commun., 42, 1848 (2012); doi:10.1080/00397911.2010.545165.

S. Nakaiida, S. Kato, O. Niyomura, M. Ishida, F. Ando and J. Koketsu, Phosphorus Sulfur Rel. Elem., 185, 930 (2010); doi:10.1080/10426501003769728.

B. Kongkathip, S. Akkarasamiyo, K. Hasitapan, P. Sittikul, N. Boonyalai and N. Kongkathip, Eur. J. Med. Chem., 60, 271 (2013); doi:10.1016/j.ejmech.2012.12.006.

H. Chen, X.F. Xu, L. Liu, G. Tang and Y.F. Zhao, RSC Adv., 3, 16247 (2013); doi:10.1039/c3ra42887g.

R. Subirós-Funosas, L. Nieto-Rodriguez, K.J. Jensen and F. Albericio, J. Pept. Sci., 19, 408 (2013); doi:10.1002/psc.2517.

S. Balalaie, M. Mahdidoust and R. Eshaghi-Najafabadi, Chin. J. Chem., 26, 1141 (2008); doi:10.1002/cjoc.200890204.

S. Balalaie, M. Mahdidoust and R. Eshaghi-Najafabadi, J. Iran.Chem. Soc., 4, 364 (2007); doi:10.1007/BF03245987.

M.Z.A. Badr, M.M. Aly, S.A. Mahgoub, A.M. Fahmy and A.A. Atallah, Bull. Chem. Soc. Jpn., 61, 1779 (1988); doi:10.1246/bcsj.61.1779.

E.A. Dikusar and N.A. Zhukovskaya, Russ. J. Org. Chem., 44, 1389 (2008); doi:10.1134/S1070428008090248.

S. Nakaiida, S. Kato, O. Niyomura, M. Ishida, F. Ando and J. Koketsu, Phosphorus Sulfur Rel. Elem., 185, 930 (2010); doi:10.1080/10426501003769728.

C.R. Hauser and G. Vermillion, J. Am. Chem. Soc., 63, 1224 (1941); doi:10.1021/ja01850a017.

A.R. Katritzky, A.A.A. Abdel-Fattah, A.V. Gromova, R. Witek and P.J. Steel, J. Org. Chem., 70, 9211 (2005); doi:10.1021/jo051231x.

W. Renfrow, J. White, R. Wolf and W. Bohl, J. Org. Chem., 33, 150 (1968); doi:10.1021/jo01265a601.

L. Gass and F.W. Bope, J. Am. Pharm. Assoc., 48, 186 (1959); doi:10.1002/jps.3030480314.

J.K. Twibanire and T.B. Grindley, Org. Lett., 13, 2988 (2011); doi:10.1021/ol201005s.

B. Movassagh, S. Balalaie and P. Shaygan, ARKIVOC, 47 (2007); doi:10.3998/ark.5550190.0008.d07.

M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Daniels, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith and M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03 (Revision A.1), Gaussian, Inc., Pittsburgh, PA (2004).

Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

A Novel Synthesis of Carboxylic Acid Oxime Esters Catalyzed by 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium Tetrafluoroborate

Corresponding Author(s) : Jiming Zhang

Abstract

Keywords

Full Article

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