Cascade embedding triethyltryptophanium iodide ionic liquid (TrpEt3+I−) on silicated titanomagnetite core (Fe3‐xTixO4‐SiO2@TrpEt3+I−): A novel nano organic–inorganic hybrid to prepare a library of 4‐substituted quinoline‐2‐carboxylates and 4,6‐disubstituted quinoline‐2‐carboxylates

化学 碘化物 喹啉 碘甲烷 离子液体 区域选择性 碘化铵 有机化学 催化作用
作者
Kobra Nikoofar,Fatemeh Molaei Yielzoleh
出处
期刊:Journal of The Chinese Chemical Society [Wiley]
卷期号:68 (8): 1549-1562 被引量:4
标识
DOI:10.1002/jccs.202000444
摘要

Abstract A library of substituted quinolone‐2‐carboxylates (4,6‐disubstituted quinolone‐2‐carboxylates, 6‐substituted quinoline dialkyl‐2,4‐dicarboxylates, and 6‐substituted 4‐[2‐methoxy‐2‐oxoethyl]quinoline‐2‐methylcarboxylates) was obtained through different scopes of one‐pot and one‐step MCRs such as (a) three‐component reaction of aromatic amines, dialkyl acetylenedicarboxylates, and terminal alkenes/ketones; (b) pseudo three‐component reaction of anilines and dialkyl acetylenedicarboxylates; and (c) pseudo three‐component reaction of anilines and methyl propiolate under solvent‐free conditions at 100°C. The promoter of these annulation processes is a novel inorganic–organic core–shell that was obtained from silicated titanomagnetite, tryptophan amino acid, and ethyl iodide. The tryptophan embedded on the silicated titanomagnetite core (Fe 3‐x Ti x O 4 ‐SiO 2 ) followed by alkylation with ethyl iodide subsequently result in in situ preparation of triethyltryptophanium iodide ionic liquid (TrpEt 3 + I − ). The final nanohybrid (Fe 3‐x Ti x O 4 ‐SiO 2 @TrpEt 3 + I − ) was characterized by field‐emission scanning electron microscope, EDAX, FT‐IR, TGA/DTG, vibrating sample magnetometer, and X‐ray fluorescence techniques. The highlighted features of the protocol are as follows: (a) synthesis of a vast range of substituted quinolines through a straightforward method from simple substrates under solvent‐free conditions, (b) utilizing various scopes of functionalities as substrates, (c) simple separation of the nano promoter via an external magnet, (d) regioselectivity in the cascade annulation procedure, and (e) recovery and reusability of the nanocomposite within three runs without significant activity loss.

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