3298-16-6Relevant academic research and scientific papers
PROCESS FOR PREPARING LACTAMS
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Paragraph 0087; 0088; 0089; 0090; 0091; 0092, (2015/02/25)
The present invention relates to a method for preparing lactams using heterogeneous catalysis by hydrogenating at least one compound of the following formula (I), where A is a radical of the following formula (I′) or (II′): —CH(R1)—CH(R2)— (I′); or —CH(R1)—CH(R2)—CH(R3)— (II′); where R1, R2 and R3 are, independently from each other, H, OH, an alkyl radical, or a cycloalkyl radical; and R is H or a straight or branched alkyl radical having 1 to 20, preferably 1 to 10, and more preferably 1 to 4 carbon atoms. Said method is carried out at a pressure of less than 60 bars, preferably 10 to 50 bars, in the presence of a solid hydrogenation catalyst including at least two metals selected from the group of noble metals and transition metals, and an inert substance used as a support, wherein said compound of formula (I) can be used alone or as part of a mixture.
Oxidant-free conversion of cyclic amines to lactams and H2 using water as the oxygen atom source
Khusnutdinova, Julia R.,Ben-David, Yehoshoa,Milstein, David
supporting information, p. 2998 - 3001 (2014/03/21)
Direct conversion of cyclic amines to lactams utilizing water as the only reagent is catalyzed by pincer complex 2. In contrast to previously known methods of amine-to-amide conversion, this reaction occurs in the absence of oxidants and is accompanied by liberation of H2, with water serving as a source of oxygen atom. Formation of a cyclic hemiaminal intermediate plays a key role in enabling such reactivity. This represents an unprecedented, conceptually new type of amide formation reaction directly from amines and water under oxidant-free conditions.
Chemoenzymic Production of Lactams from Aliphatic α,ω-Dinitriles
Gavagan, John E.,Fager, Susan K.,Fallon, Robert D.,Folsom, Patrick W.,Herkes, Frank E.,Eisenberg, Amy,Hann, Eugenia C.,DiCosimo, Robert
, p. 4792 - 4801 (2007/10/03)
Five- and six-membered ring lactams have been prepared by first converting an aliphatic α,ω-dinitrile to an ω-cyanocarboxylic acid ammonium salt, using a microbial cell catalyst having an aliphatic nitrilase activity (Acidovorax facilis 72W, ATCC 55746) or a combination of nitrile hydratase and amidase activities (Comamonas testosteroni 5-MGAM-4D, ATCC 55744). The ω-cyanocarboxylic acid ammonium salt was then directly converted to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate ω-cyanocarboxylic acid or ω-aminocarboxylic acid. Only one of two possible lactam products was produced from α-alkyl-substituted α,ω-dinitriles, where the nitrilase of A. facilis 72W regioselectively hydrolyzed only the ω-cyano group to produce a single cyanocarboxylic acid ammonium salt in greater than 98% yield.
PREPARATION OF LACTAMS VIA OXIDATION OF CYCLIC, TERTIARY AND SECONDARY AMINES WITH Hg(II)-EDTA COMPLEX IN ALKALINE MEDIUM
Wenkert, Ernest,Angell, E. Charles
, p. 1331 - 1338 (2007/10/02)
Oxidation of N-alkylpiperidines and other cyclic, tertiary amines with Hg(II)-EDTA complex in basic solution yields lactams, similar oxidation of N-hydroxypiperidines gives hydroxamic acids (presumably via nitrones) and oxidation of N-unsubstituted piperidines affords lactams, probably via 1-piperidine trimers.
