Synthesis of 2-Halo-3-Formylindoles via Vilsmeier–Haack Haloformylation Reaction of Oxindole
Peng Zhao
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorMingyu Jiang
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorJiahui Li
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorJuan Feng
Teaching Affairs Department , Southwest Petroleum University , Chengdu , 637001 , Sichuan, China , swpu.edu.cn
Search for more papers by this authorShiyi Tang
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorPengluo Wei
Clinical Medical College , North Sichuan Medical College , Nanchong , Sichuan, China , nsmc.edu.cn
Search for more papers by this authorCorresponding Author
Hua Zhang
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorPeng Zhao
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorMingyu Jiang
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorJiahui Li
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorJuan Feng
Teaching Affairs Department , Southwest Petroleum University , Chengdu , 637001 , Sichuan, China , swpu.edu.cn
Search for more papers by this authorShiyi Tang
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorPengluo Wei
Clinical Medical College , North Sichuan Medical College , Nanchong , Sichuan, China , nsmc.edu.cn
Search for more papers by this authorCorresponding Author
Hua Zhang
Department of Pharmacology , North Sichuan Medical College , Nanchong , 637100 , Sichuan, China , nsmc.edu.cn
Institute of Materia Medica of North Sichuan Medical College , Nanchong , Sichuan, China
Search for more papers by this authorAbstract
A series of 2-halo-3-formylindole molecules were synthesized via Vilsmeier–Haack haloformylation reaction of N-Boc-oxindole with POCl3 or POBr3 and DMF, which are free from the use of catalyst and solvent. Moreover, through several simple postprocessing steps, corresponding adducts can be readily transformed to Tenidap analog intermediate. The feasibility of gram-scale experiments proved that the methodology has the potential to be scaled. In addition, a possible reaction mechanism was proposed based on control experiments.
Conflicts of Interest
The authors declare no conflicts of interest.
Open Research
Data Availability Statement
The data supporting this article have been included as part of the Supporting Information.
Supporting Information
| Filename | Description |
|---|---|
| joch8562391-sup-0001-f1.pdfPDF document, 4.8 MB | Supporting Information The supporting information contains the detail of reaction condition screening, experimental procedures, nuclear magnetic resonance of hydrogen and carbon 13 spectra, melting point of solid product, crystallographic data, and high-resolution mass spectra of the prepared compounds. |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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