A New Approach for the Synthesis of 6,7-Dihydro-5H-Cyclopenta[b]pyridine

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Abstract:

A new practical and efficient route was developed for the synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridine, which is a key intermediate of cefpirome. Leading to the formation of the corresponding product, nucleophilic addition, acetylization, Vilsmeier cyclization reaction and dechlorination were employed under mild reaction conditions by using commercially available cyclopentanone and benzylamine as raw materials. The total yield of this newly developed synthetic route for the target product was 43.15% with 99.7% of purity (HPLC). The structure of target molecular was confirmed by LC-MS and 1H NMR spectrum.

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Advanced Materials Research (Volumes 634-638)

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1211-1214

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January 2013

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© 2013 Trans Tech Publications Ltd. All Rights Reserved

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[1] D. E. Beattie, R. Crossley and A. C. Curran: Journal of Medicinal Chemistry. Vol. 20 (1977), p.714

Google Scholar

[2] T. L. Lemke, T. W. Shak and L. A. Cates: Journal of Medicinal Chemistry. Vol. 20 (1977), p.1351

Google Scholar

[3] G. Seibert, N. Klesel and M. Limbert: Arzneimittle Forschung. Vol. 33 (1983), p.1084

Google Scholar

[4] R. E. Hancock and F. Bellido: Journal of Antimicrobial Chemotherapy. Vol. 29 (1992), p.1

Google Scholar

[5] H. Beschke, H. Friedrich and H. Offermanns: U.S. Patent 4, 332, 940 (1982)

Google Scholar

[6] S. Takayuki, G. Nobuo and N. Tour: J.P. 2, 045, 470 (1990)

Google Scholar

[7] Z. W. Feng, X. Q Zhao: Chinese Journal of Pharmaceuticals. Vol. 38(7) (2007), p.621

Google Scholar

[8] A. Gorgio, A. Antonio and B. Gabriele: Journal of Organic Chemistry. Vol. 68 (2003), p.6959

Google Scholar

[9] Y. G. Ge, W. M. Mo and Z. L. Shen: Chinese Journal of Pharmaceuticals. Vol. 37 (9) (2006), p.586

Google Scholar

[10] P. Gong, Y. F. Zhao and D. S. Yu: Journal of Shenyang Pharmaceuticals University. Vol. 18 (2) (2001), p.102

Google Scholar

[11] S. Hesse and G. Kirsch: Tetrahedron Letters.Vol. 43 ( 2002), p.1213

Google Scholar

[12] W. K. Su, Y. Y. Weng and L. Jiang: Organic Preparations and Procedures International. Vol. 42 (6) (2010), p.503

Google Scholar

[13] J. J. Li: Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications [M]. Springer. ( 2009), p.558

Google Scholar