280-70-6Relevant articles and documents
One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis
Coeck, Robin,De Vos, Dirk E.
supporting information, p. 5105 - 5114 (2020/08/25)
The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).
Concise syntheses of bridged morpholines
Zaytsev, Andrey V.,Pickles, James E.,Harnor, Suzannah J.,Henderson, Alistair P.,Alyasiri, Mohammed,Waddell, Paul G.,Cano, Celine,Griffin, Roger J.,Golding, Bernard T.
, p. 53955 - 53957 (2016/07/06)
Concise and practical syntheses of 8-oxa-3-aza-bicyclo[3.2.1]octane and 9-oxa-3-aza-bicyclo[3.3.1]nonane are described starting from furan-2,5-dicarboxylic acid and 4H-pyran-2,6-dicarboxylic acid, respectively, and using a solvent-free step for a key cyclisation.
PROCESS FOR THE REDUCTIVE AMINATION OF ALDEHYDES AND KETONES
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Page/Page column 18-19, (2008/12/06)
Aldehyde or ketone compounds having more than one carbonyl group are reductively aminated to form a product amine compound having more than one primary amino group. The aldehyde or ketone compound is reacted with the product amine compound in the presence of an alcohol solvent, to form a reaction mixture that contains one or more intermediates. The intermediate is then reductively aminated to form the desired product. This process may produce the desired product in very high yields with low levels of secondary amine impurities.
PROCESS FOR THE REDUCTIVE AMINATION OF ALDEHYDES AND KETONES VIA THE FORMATION OF MACROCYCLIC POLYIMINE INTERMEDIATES
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Page/Page column 18-19, (2008/06/13)
Aldehyde or ketone compounds having more than one carbonyl group are reductively aminated to form a product amine compound having more than one primary amino group. The aldehyde or ketone compound is reacted with the product amine compound, to form a reaction mixture that contains one or more intermediates. The intermediate is then reductively aminated to form the desired product. This process produces the desired product in very high yields with low levels of secondary amine impurities.
Structure, conformation, and stereodynamics of N-nitroso-2,4-diaryl-3-azabicyclo[3.3.1]nonanes and N-nitroso-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones
Po?on?ski, Tadeusz,Pham, Marzena,Milewska, Maria J.,Gdaniec, Maria
, p. 3766 - 3772 (2007/10/03)
The variable temperature 1H, 13C, and 19F NMR spectra were measured for the title N-nitrosamines. The observed unusually low N-N rotation barriers (12-15 kcal/mol) result from a significant deviation of the nitrosamino system from planarity. A pyramidal character of the amino nitrogen was confirmed by the X-ray crystal structures of two compounds and by bathochromic shifts of the n-π* absorption bands in the UV spectra. The nonplanarity of the nitrosamino moiety is due to the strong pseudoallylic A(1,3) strain caused by the steric interaction of the NNO group with the neighboring aryl substituents fixed in the equatorial positions of the bicyclic skeleton. In addition, the barriers to the C-C rotation of aryl groups were examined at temperatures lower than required to "freeze" the N-N rotation and different ΔG? values were observed for the aryls oriented syn and anti to the nitroso oxygen.
