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Utilization of Solid Acid SO 4 2 − /TiO 2 as Catalyst to the Three‐Component Mannich Reaction at Ambient Temperature
Author(s) -
Yao Yuanyong,
Zhang Meng,
Chen Shixue,
Xing Mingming,
Shu Hua
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2825
Subject(s) - chemistry , catalysis , mannich reaction , aldimine , lewis acids and bases , calcination , aldehyde , amine gas treating , brønsted–lowry acid–base theory , organic chemistry , medicinal chemistry , polymer chemistry
The three‐component Mannich reaction of among dimethyl malonate, aromatic primary amine, and aromatic aldehyde was made successfully in the presence of solid acidic catalyst SO 4 2 − /TiO 2 , with excellent catalytic activity, as compared to SO 4 2 − /γ‐Al 2 O 3 and SO 4 2 − /ZnO. To the best of our knowledge, SO 4 2 − /TiO 2 prepared at varied calcination temperatures can perform different intensities of Lewis and Brønsted acidities. Because of this point, under the optimum conditions, the effect of SO 4 2 − /TiO 2 (prepared at 200°C) was much more than that of SO 4 2 − /TiO 2 (prepared at 300°C or 400°C) in the three‐component Mannich reaction. In observing ionization activation mode of the three‐component Mannich reaction, it disclosed that the plausible mechanism possibly undergoes formation of aldimines and transformation of aldimines into β ‐amino esters by applying solid acidic catalyst SO 4 2 − /M x O y .