Eco-Friendly Synthesis of Sulphonic Acid Oxime Esters Catalyzed by 2-(1H-Benzotriazole-1-yl)-1,1,3,3-Tetramethyluronium Tetrafluoroborate

Abstract:

Herein we describle a facile synthesis of sulphonic acid oxime esters in acetonitrile from the corresponding sulphonic acids and oximes catalyzed by the environmental friendly 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) in the presence of triethylamine (TEA) under mild conditions. The present approach offers the advantages of a clean reaction, simple methodology, employing readily available catalyst, short reaction duration, high selectivity and high yield.

• Periodical: Applied Mechanics and Materials (Volume 525)
• Pages: 93-96
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.525.93
• Online since: February 2014
• Authors: Wei Shi*, Ji Ming Zhang, Jian Hua Zhou, Jian Hua Zhou, Song Song Ding
• Keywords: Eco-Friendly, Oxime Ester, Oxime esterification, Sulphonic Acid, TBTU

References

[1] A. Karakurt, M. A. Alagoz, B. Sayoglu, U. Calis and S. Dalkara, Eur. J. Med. Chem., 57 (2012), p.275.

[2] G. Surkau, K. J. Boehm, K. Mueller and H. Prinz, Eur. J. Med. Chem., 45 (2010), p.3354.

[3] Y.J. Cui, X. P. Rao, S. B. Shang, S. Jie and Y. Q. Gao, Lett. Drug Des. Discov., 10 (2013), p.102.

[4] H. Q. Zhao, M. J. Zhou, L. F. Duan, W. Wang, J. J. Zhang, D. Q. Wang and X. M. Liang, Molecules, 18 (2013), p.3615.

[5] C. D. Magnusson and G. G. Haraldsson, Chem. Phys. Lipids, 165 (2012), p.712.

[6] R. F. Sun, Y. Q. Li, M. Y. Lue, L. X. Xiong and Q. M. Wang, Bioorg. Med. Chem. Lett., 20 (2010), p.4693.

[7] 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 (2013), p.1735.

DOI: 10.1021/jo302149u

[8] J. Xu, G. L. Ma, K. M. Wang, J. M. Gu, S. Jiang and J. Nie, J. Appl. Polym. Sci., 123 (2012), p.725.

[9] S. S. P. Chou, J. C. Juan, S. C. Tsay, K. P. Huang and J. R. Hwu, Molecules, 17 (2012), p.3370.

[10] C. Dworak and R. Liska, J. Polym. Sci. A1, 48 (2010), p.5865.

[11] S. B. Liu, Y. Yu and L. S. Liebeskind, Org. Lett., 9 (2007), p. (1947).

[12] D. J. Ritson, R. J. Cox and J. Berge, Org. Biomol. Chem., 2 (2004), p. (1921).

[13] S. K. Kundu, M. Rahman, P. Dhara, A. Hajra and A. Majee, Synthetic Commun., 42 (2012), p.1848.

[14] S. Nakaiida, S. Kato, O. Niyomura, M. Ishida, F. Ando and J. Koketsu, Phosphorus Sulfur, 185 (2010), p.930.

[15] B. Kongkathip, S. Akkarasamiyo, K. Hasitapan, P. Sittikul, N. Boonyalai and N. Kongkathip, Eur. J. Med. Chem., 60 (2013), p.271.

DOI: 10.1016/j.ejmech.2012.12.006

[16] H. Chen, X. F. Xu, L. Liu, G. Tang and Y. F. Zhao, RSC Adv., 3 (2013), p.16247.

[17] R. Subirós-Funosas, L. Nieto-Rodriguez, K. J. Jensen, F. Albericio, J. Pept. Sci., 19 (2013), p.408.

DOI: 10.1002/psc.2517

[18] S. Balalaie, M. Mahdidoust and R. Eshaghi-Najafabadi, Chinese J. Chem., 26 (2008), p.1141.

[19] S. Balalaie, M. Mahdidoust and R. Eshaghi-Najafabadi, J. Iran. Chem. Soc., 4 (2007), p.364.

[20] J. K. Twibanire and T. B. Grindley, Org. Lett., 13 (2011), p.2988.

[21] B. Movassagh, S. Balalaie and P. Shaygan, Arkivoc, 13 (2007), p.47.