Fullerotetrahydroquinolines: TfOH/TsOH ⋅ H2O‐Mediated One‐Pot Two‐Step Synthesis and N‐Alkylation/Acylation/Carboamidation Reaction. Issue 18 (29th July 2021)

• Record Type: Journal Article
• Authors: Liu, Xiong; Wang, Xing‐Yu; Sun, Rui; Huang, Min‐Rong; Liu, Xiu‐Shan; Wang, Hui‐Juan; Li, Fa‐Bao; Liu, Xu‐Feng; Liu, Li; Liu, Chao‐Yang
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 18(2021)
• Page Start: 4399
• Page End: 4421
• Publication Date: 2021-07-29
• Subjects: [60]fullerene -- fullerotetrahydroquinolines -- alkylation -- acylation -- carboamidation; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100659
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :