A Novel and Practical Synthesis of Tryptanthrin

Yong He; Shiyun Chen; Yonghao Gao; Shuangying Gui; Yisi Feng

doi:10.1055/a-1878-8448

Synthesis, Table of Contents

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

paper

A Novel and Practical Synthesis of Tryptanthrin

Authors

Yong He

^aSchool of Chemistry and Chemical Engineering, Hefei University of Technology,Hefei 230009, P. R. of China

^bAnhui Province Key Laboratory of Pharmaceutical Preparation Technology and Application, Hefei 230012, P. R. of China
Shiyun Chen

^cAnalytical &Testing Center, Hefei University, Hefei230601
Yonghao Gao

^aSchool of Chemistry and Chemical Engineering, Hefei University of Technology,Hefei 230009, P. R. of China
Shuangying Gui

^bAnhui Province Key Laboratory of Pharmaceutical Preparation Technology and Application, Hefei 230012, P. R. of China

^dDepartment of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012, P. R. of China
Yisi Feng∗

^aSchool of Chemistry and Chemical Engineering, Hefei University of Technology,Hefei 230009, P. R. of China

Abstract

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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

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References

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