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Synthesis 2022; 54(20): 4509-4512
DOI: 10.1055/a-1878-8448
paper

A Novel and Practical Synthesis of Tryptanthrin

Yong He
a   School of Chemistry and Chemical Engineering, Hefei University of Technology,Hefei 230009, P. R. of China
b   Anhui Province Key Laboratory of Pharmaceutical Preparation Technology and Application, Hefei 230012, P. R. of China
,
Shiyun Chen
c   Analytical &Testing Center, Hefei University, Hefei230601
,
Yonghao Gao
a   School of Chemistry and Chemical Engineering, Hefei University of Technology,Hefei 230009, P. R. of China
,
Shuangying Gui
b   Anhui Province Key Laboratory of Pharmaceutical Preparation Technology and Application, Hefei 230012, P. R. of China
d   Department of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012, P. R. of China
,
Yisi Feng∗
a   School of Chemistry and Chemical Engineering, Hefei University of Technology,Hefei 230009, P. R. of China
› Author AffiliationsThe Key project of Anhui Provincial Department of Education, China (NO. KJ2020A672) and The Open Fund Project of Anhui Key Laboratory of Pharmaceutical Preparation Technology and Application (NO. 2021KFKT01 and 2021KFKT08).
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Abstract

Tryptanthrin was synthesized through a two-step reaction of oxidation and condensation in a one-pot method, with isatin and sodium hypochlorite as starting materials. The influence of sodium hypochlorite, acetonitrile dosage, oxidation reaction temperature, and reaction time on the yield of the target product during the reaction was investigated. The following optimal reaction conditions were obtained: the ratio of n (isatin) to n (sodium hypochlorite) was 2:1, and the reaction time was 6–8 hours at room temperature. The structure of tryptanthrin was confirmed by matching the IR, NMR, and mass data with the literature report. The study shows that the chemical reaction route designed in this report is short, with high yield and purity of the target product. Its low production cost and simple operation method are expected to be applicable to industrial production.

Key words

isatin - sodium hypochlorite - Baeyer–Villiger oxidation rearrangement - tryptanthrin

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1878-8448.
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Publication History

Received: 24 April 2022

Accepted after revision: 20 June 2022

Accepted Manuscript online:
20 June 2022

Article published online:
02 August 2022

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