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Studies were conducted to measure the relative rates of aldimine formation from aldehydes and primary amines in different solvents, namely THF, DCE, and MeOH without added catalysts or dehydrating agents. However, imine formations from carbonyl compounds and primary amines are reversible reactions that require long reaction times and the use of a dehydrating agent such as molecular sieves or the azeotropic removal of water to drive the reaction to completion. 131 The problem of undesired dialkylation reactions was solved in these cases by conducting fast reductions of preformed imines to minimize the coexistence of product amines with unreacted imines. Surprisingly, the dialkylation happens in some reactions even when excess amine was used or when the reaction was carried out with a ‘preformed imine’ and no excess aldehyde was present. Typically, this undesired side reaction is suppressed by simply adding a slight excess of the primary amine, but that is not a general solution. However, there were some cases where the formation of significant amounts of dialkylation was observed. Reductive amination of aldehydes with primary amines is the easiest reductive amination procedure. Combination of the IL with (EtO) 3SiH showed better performance than the best metal-based catalyst reported previously.
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Reactions proceed under mild conditions, even at room temperature, affording the lactamic products 38 in good to excellent yields ( Scheme 13).
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Looking for a metal-free procedure, a series of lactate-based TSILs with different cations were developed, which were capable of efficiently catalyzing the reductive amination/cyclization of Levulinic acid, by using hydrosilane as reducing agent without any metal catalysts or additives. Various metal-based catalysts have been explored for the Levulinic acid reductive amination to produce lactams or pyrrolidines using different reducing agents. Reductive amination/cyclization of Levulinic acid (a naturally occurring keto-acid) is a promising route for the synthesis of N-alkyl-5-methyl-2-pyrrolidones (lactams), that are important structural motifs with wide applications in pharmaceutical, agrochemical, and material industries.