10285-87-7Relevant articles and documents
Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
, p. 4297 - 4306 (2019/08/26)
Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.
Oxidation of amines over alumina based catalysts
Rakottyay, Karol,Kaszonyi, Alexander,Vají?ek, Stanislav
experimental part, p. 33 - 41 (2010/08/22)
Amines were oxidized by molecular oxygen in the vapor phase at atmospheric pressure over alumina and silicotungstic acid/alumina catalysts. The study is focused on the influence of structure of amine and catalyst properties on the composition of the main reaction products and byproducts. Coating of γ-Al2O3 with silicotungstic acid or its semisalt can significantly enhance its catalytic activity in amine oxidation. The adsorption of amine on weak acidic sites of catalyst is essential for its oxidation to main reaction products. Cycloalkylamines are oxidized mainly to cyclic oximes (selectivity up to 64%) and Schiff bases of appropriate cycloalkanone and cycloalkylamine (selectivity up to 38%). Mainly nitriles (selectivity up to 55%) and appropriate Schiff bases (selectivity up to 54%) were observed in the oxidation products of primary alkylamines. Their molar ratio depends on the catalyst acidity and reaction conditions. 1,6-Hexanediamine is oxidized mainly to caprolactam (yield 48%) and other cyclic lactames and Schiff bases as well as to dinitrile (yield 13%).
Benzamidines, alkamidines and formamidines formed by use of aryl- and alkyliminodimagnesium: Molar ratio and structure of reagent governing the reaction
Okubo, Masao,Omote, Yasumasa
, p. 212 - 220 (2007/10/03)
In order to extend the the method for preparation of amidines using N-Mg reagents, aryl- and alkyliminodimagnesium [IDMg, ArN(MgBr)2 and RN(MgBr)2] were reacted with esters, amides, ortho- esters, acetals, aminoacetal and arene- and
