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Vol. 27 No. 9 (2015): Vol 27 Issue 9

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An Improved Synthetic Method of Phenazine-1-carboxylic Acid

https://doi.org/10.14233/ajchem.2015.18757
Q.Y. Zhan
Department of Applied Chemistry, College of Sciences, Nanjing Tech University, Nanjing 211816, P.R. China
X.L. Zhu
Department of Applied Chemistry, College of Sciences, Nanjing Tech University, Nanjing 211816, P.R. China
H. Huang
Department of Applied Chemistry, College of Sciences, Nanjing Tech University, Nanjing 211816, P.R. China
Q. Liu
Department of Applied Chemistry, College of Sciences, Nanjing Tech University, Nanjing 211816, P.R. China
H.J. Zhu
Department of Applied Chemistry, College of Sciences, Nanjing Tech University, Nanjing 211816, P.R. China

Corresponding Author(s) : H.J. Zhu

zhuhj@njtech.edu.cn

Asian Journal of Chemistry, Vol. 27 No. 9 (2015): Vol 27 Issue 9

Abstract

An improved synthetic method of a natural fungicide, phenazine-1-carboxylic acid, was reported. In brief, the process constitutes of (a) one-pot synthesis of 1-methyphenazine (IV) from pyrocatechol and 3-methyl-2-aminoaniline, (b) Wohl-Ziegler bromination of IV, (c) hydrolyzation of 1-bromomethylphenazine (III) in aqueous solution of Na2CO3/N,N-dimethylformamide (1.1:1, v/v), (d) oxidation of 1-phenazinemethanol (II) by O2 under the catalyzation of N-bromosuccinimide. This method provided an effective synthesis of phenazine-1-carboxylic acid in the overall yield of 66 %.

Keywords

Natural fungicide Phenazine-1-carboxylic acid One-pot Oxidation
Zhan, Q., Zhu, X., Huang, H., Liu, Q., & Zhu, H. (2015). An Improved Synthetic Method of Phenazine-1-carboxylic Acid. Asian Journal of Chemistry, 27(9), 3355–3360. https://doi.org/10.14233/ajchem.2015.18757
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