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Fullerotetrahydroquinolines: TfOH/TsOH ⋅ H2O-Mediated One-Pot Two-Step Synthesis and N-Alkylation/Acylation/Carboamidation Reaction
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-07-20 , DOI: 10.1002/adsc.202100659
Xiong Liu 1 , Xing-Yu Wang 1 , Rui Sun 1 , Min-Rong Huang 1 , Xiu-Shan Liu 1 , Hui-Juan Wang 1 , Fa-Bao Li 2 , Xu-Feng Liu 1 , Li Liu 2 , Chao-Yang Liu 1
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A series of N-unsubstituted/substituted fullerotetrahydroquinolines without a directly attached nitrogen atom were synthesized in moderate to good yields via a one-pot two-step reaction of [60]fullerene with arylamines and paraformaldehyde in the presence of trifluoromethanesulfonic acid and p-toluenesulfonic acid monohydrate. Aromatic primary amines produce N-unsubstituted fullereotetrahydroquinolines, while aromatic secondary amines give N-substituted fullereotetrahydroquinoline derivatives. As precursors, N-unsubstituted fullerotetrahydroquinolines could be further derivatized by the N-alkylation/acylation/carboamidation reactions to produce a large variety of N-substituted fullerotetrahydroquinolines containing Cl, NO2, C(O), and C(O)NH functional groups, which may have applications in the field of perovskite-based solar cells. Plausible reaction pathways for the formation of N-unsubstituted/substituted fullerotetrahydroquinolines were suggested to elucidate the above-mentioned reaction process.

中文翻译:

富勒四氢喹啉:TfOH/TsOH ⋅ H2O 介导的一锅两步合成和 N-烷基化/酰化/碳酰胺化反应

在三氟甲磺酸和甲苯磺酸的存在下,通过 [60] 富勒烯与芳胺和多聚甲醛的一锅两步反应,合成了一系列没有直接连接氮原子的N-未取代/取代的富勒四氢喹啉。酸一水合物。芳族伯胺产生Ñ -未被取代fullereotetrahydroquinolines,而芳族仲胺,得到Ñ取代fullereotetrahydroquinoline衍生物。作为前体,N-未取代的富勒四氢喹啉可以通过N-烷基化/酰化/碳酰胺化反应进一步衍生,以产生多种N含有Cl、NO 2、C(O) 和C(O)NH 官能团的-取代的富勒四氢喹啉,可能在基于钙钛矿的太阳能电池领域有应用。提出了形成N-未取代/取代的富勒四氢喹啉的合理反应途径来阐明上述反应过程。
更新日期:2021-09-21
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