Practical Fischer Indolization Using Bench-Stable Arylhydrazine Sulfonate as the Surrogate of Arylhydrazine

Author:

Zhu Yanping1,Dong Kaiwu2ORCID,Li Wenjuan12,Shen Chaoren2

Affiliation:

1. School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University

2. Shanghai Frontiers Science Center of Molecule Intelligent Syntheses & Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University

Abstract

AbstractFischer indolization using bench-stable sodium arylhydrazine sulfonate as a surrogate of arylhydrazine was developed. The preparation of arylhydrazine sulfonate was also modified by replacing sodium sulfite reductant with Pd-catalyzed hydrogen transfer. The straightforward synthesis of tetrahydrocarbazoles from the corresponding anilines was successfully conducted in a one-pot manner. A practical application of this method was demonstrated in the formal synthesis of pharmaceutical molecules Rizatriptan and Zolmitriptan.

Funder

Shanghai Rising-Star Program

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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