6220-79-7Relevant articles and documents
Biocatalytic Aza-Michael Addition of Aromatic Amines to Enone Using α-Amylase in Water
Dutt, Sunil,Goel, Vanshita,Garg, Neha,Choudhury, Diptiman,Mallick, Dibyendu,Tyagi, Vikas
supporting information, p. 858 - 866 (2020/01/03)
The Michael addition of amines with enones for synthesizing β-amino carbonyls constitutes a valuable transformation in organic chemistry. While various catalyst have been made available for catalyzing the Michael addition of aromatic amines to enones but
Iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to form β-aminoketones and Benzo[h]quinolones
Miao, Changqing,Jiang, Liya,Ren, Lanhui,Xue, Qingxia,Yan, Fang,Shi, Weiwei,Li, Xinjian,Sheng, Jiwen,Kai, Shuangshuang
, p. 2215 - 2228 (2019/02/27)
An iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to yield β-aminoketones and benzo[h]quinolones had been developed. Noble metallic catalysts, oxidants, α β-unsaturated ketone intermediates and aza-Michael addition were not involved in this coupling reaction which made it unique when compared to other reactions reported in literature. Inexpensive iodine catalyst, easy accessible raw materials, mild reaction conditions, good functional group tolerance and excellent selectivity made this coupling reaction be a practical method. This reaction can also be scaled up.
TBN-Catalyzed Dehydrative N-Alkylation of Anilines with 4-Hydroxybutan-2-one
Cheng, Wenchen,Deng, Shue,Jiang, Liya,Ren, Lanhui,Wang, Zicheng,Zhang, Jian,Song, Weiguo
supporting information, p. 7372 - 7377 (2019/11/28)
Until now, the substitution of alcohols by N-nucleophiles via TBN-catalyzed dehydrogenation was not known. Herein, we reported a TBN catalyzed dehydrative N-alkylation of anilines with 4-hydroxybutan-2-one in the presence of TEMPO, which was different from the TEMPO/TBN catalyzed oxidation reactions. A range of anilines reacted successfully with 4-hydroxybutan-2-one to generate the N-monoalkylation products in good yields. Mechanistic studies revealed that this reaction most possibly proceeded through aza-Michael addition. Water was the only by-product, making it more environmentally friendly. The gram-scale reactions verified the synthetic practicality of this protocol.