An improved synthetic method of phenazine-1-carboxylic acid

Q. Y. Zhan; X. L. Zhu; H. Huang; Q. Liu; H. J. Zhu

doi:10.14233/ajchem.2015.18757

An improved synthetic method of phenazine-1-carboxylic acid

Q. Y. Zhan, X. L. Zhu, H. Huang, Q. Liu, H. J. Zhu

Research output: Contribution to journal › Article › peer-review

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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 %.

Original language	English (US)
Pages (from-to)	3355-3360
Number of pages	6
Journal	Asian Journal of Chemistry
Volume	27
Issue number	9
DOIs	https://doi.org/10.14233/ajchem.2015.18757
State	Published - Sep 1 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry

Keywords

Natural fungicide
One-pot
Oxidation
Phenazine-1-carboxylic acid

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10.14233/ajchem.2015.18757

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AU - Zhan, Q. Y.

AU - Zhu, X. L.

AU - Huang, H.

AU - Liu, Q.

AU - Zhu, H. J.

PY - 2015/9/1

Y1 - 2015/9/1

N2 - 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 %.

AB - 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 %.

KW - Natural fungicide

KW - One-pot

KW - Oxidation

KW - Phenazine-1-carboxylic acid

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An improved synthetic method of phenazine-1-carboxylic acid

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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