Acid-catalyzed Dimerization Reaction of Pyrroles to Synthesize Hexaaryl-4,8-dihydropyrrolo[2,3-f]indoles
| Autor: | Shi Shaojia, Zhang Tong, Yin Hong-zong, Jiang Lin, Zheng Ziqi, Fu Xue, Zhang Shuai |
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| Rok vydání: | 2018 |
| Předmět: |
Indole test
chemistry.chemical_classification 010405 organic chemistry Chemistry Kinetics General Chemistry Nuclear magnetic resonance spectroscopy Sulfonic acid 010402 general chemistry 01 natural sciences Chloride Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Acid catalyzed medicine Proton NMR medicine.drug Pyrrole |
| Zdroj: | Chemical Research in Chinese Universities. 34:559-563 |
| ISSN: | 2210-3171 1005-9040 |
| DOI: | 10.1007/s40242-018-8031-3 |
| Popis: | Pyrroloindoles, as a kind of promising small-melecular hole injetion materials, have attracted wide attention. Herein, we described a simple metal-free method for the synthesis of 4,8-dihydropyrrolo[2,3-f]indole compounds through the acid-catalyzed dimerization reaction of pyrroles. The structures of target 4,8-dihydropyrrolo-[2,3-f]indoles were confirmed by NMR spectrum and X-ray single crystal diffraction. Notably, pyrrole substrates were synthesized conveniently starting from available biological dipeptides. cis-Configuration was preferred when bulky p-toluene sulfonic acid(TsOH) was employed. Excessive aicds empoyed in dimerization would lead to the formation of quantitative pyrrolium chloride intermediate, restraining further conversion to target compounds. Furthermore, the dimerization process was monitored by 1H NMR spectrum, proving that it followed a second-order kinetics, providing significant insight to the mechanism of dimerization reaction. |
| Databáze: | OpenAIRE |
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