10.1021/ja01154a107
The study investigates the synthesis and biological properties of Mannich bases derived from benzalacetones. The researchers aimed to enhance the analgetic (pain-relieving) effects of γ-phenylpropylamines by preparing their vinylogous bases. The primary chemicals involved include benzalacetone, which serves as the starting material, and various secondary amines such as dimethylamine, diethylamine, morpholine, and piperidine, which are used to form the Mannich bases. Additionally, substituents like nitro, chloro, and methoxy groups are introduced into the benzene ring of benzalacetone to explore their impact on biological activity. The study found that while the synthesized vinylogous bases did not exhibit analgetic effects, they demonstrated in vitro antibacterial activity. The authors also attempted to improve the antibacterial effectiveness by introducing a p-nitro group, inspired by the antibiotic Chloromycetin, and making other structural modifications. The experimental section details the preparation of various benzalacetone derivatives and their corresponding Mannich bases, with yields and physical properties reported for each compound.
10.1016/j.tetlet.2013.05.019
The study investigates the highly enantioselective conjugate addition of nitroalkanes to enones catalyzed by cinchona alkaloid-derived primary amine. The researchers used various cinchona alkaloid-derived catalysts and cyclohexane diamine-derived bifunctional catalysts to promote the asymmetric Michael addition reaction of 4-phenylbut-3-en-2-one (2a) with nitromethane (3a). Among them, quinine amine 1i showed the most promising results, achieving good yield and high enantiocontrol. The optimized reaction conditions were explored, with THF as the solvent yielding the best results. The scope of the addition of nitroalkanes to enones was then investigated, revealing that the catalyst 1i could efficiently catalyze the conjugate addition of nitromethane to various enones, affording the desired products with excellent enantioselectivities. The study expanded the domain of organocatalyzed enantioselective conjugate addition process of nitroalkanes to enones.
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