Acid-catalyzed Dimerization Reaction of Pyrroles to Synthesize Hexaaryl-4,8-dihydropyrrolo[2,3-f]indoles  

作　　者：ZHANG Shuai ZHENG Ziqi ZHANG Tong FU Xue SHI Shaojia JIANG Lin YIN Hongzong 

机构地区：[1]College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018, P. R. China

出　　处：《Chemical Research in Chinese Universities》2018年第4期559-563,共5页高等学校化学研究（英文版）

基　　金：Supported by the Natural Science Foundation of Shandong Province, China（No.ZR2017BB025）, the University Science and Technology Program of Shandong Province, China（No.J16LC15） and the Youth Science and Technology Innovation Fund of Shandong Agricultural University, China（No.24166）.

摘　　要：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 clfloride 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.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 clfloride 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.

关 键 词：Dimerazation Pyrroloindole Benzoheterole PYRROLE 

分 类 号：O626.13[理学—有机化学] TQ028.8[理学—化学]