[3 + 2]-Annulations of N-alkyl-3-substituted indoles with quinone monoketals catalysed by Brønsted acids
| Autor: | Zhen Liu, Ji-Ping Hu, Pei-Jun Yang, Jia-Nan Chen, Gaosheng Yang, Zhuo Chai, Xue-Fei Li |
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| Rok vydání: | 2016 |
| Předmět: |
Models
Molecular Indoles 010402 general chemistry 01 natural sciences Biochemistry Catalysis chemistry.chemical_compound Benzoquinones Organic chemistry Phenyl group Molecule Physical and Theoretical Chemistry Alkyl chemistry.chemical_classification Molecular Structure 010405 organic chemistry Organic Chemistry Aromatization Substrate (chemistry) 0104 chemical sciences Quinone chemistry Cyclization Brønsted–Lowry acid–base theory Acids |
| Zdroj: | Organic & Biomolecular Chemistry. 14:1024-1030 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | An organocatalytic dearomative [3 + 2]-annulation of N-alkyl-3-alkylindoles with quinone monoketals is developed. The reaction provides a mild and straightforward way to various benzofuro[2,3-b]indolines of potential biological and pharmaceutical interest in moderate to good yields. Moreover, when 3-phenylindole, a problematic substrate in previous relevant studies, was used as the substrate under the otherwise same reaction conditions, a novel 1,2-shift of the phenyl group occurred followed by aromatization to provide 2,3-diaryl indoles useful for cancer therapy studies in moderate yields. |
| Databáze: | OpenAIRE |
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