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Fullerotetrahydroquinolines: TfOH/TsOH ⋅ H 2 O‐Mediated One‐Pot Two‐Step Synthesis and N ‐Alkylation/Acylation/Carboamidation Reaction
Author(s) -
Liu Xiong,
Wang XingYu,
Sun Rui,
Huang MinRong,
Liu XiuShan,
Wang HuiJuan,
Li FaBao,
Liu XuFeng,
Liu Li,
Liu ChaoYang
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100659
Subject(s) - chemistry , alkylation , paraformaldehyde , acylation , medicinal chemistry , organic chemistry , primary (astronomy) , catalysis , physics , astronomy
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, NO 2 , 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.