91854-79-4Relevant academic research and scientific papers
Mapping the substrate scope of monoamine oxidase (MAO-N) as a synthetic tool for the enantioselective synthesis of chiral amines
Herter, Susanne,Medina, Florian,Wagschal, Simon,Benha?m, Cyril,Leipold, Friedemann,Turner, Nicholas J.
, p. 1338 - 1346 (2017/10/06)
A library of 132 racemic chiral amines (α-substituted methylbenzylamines, benzhydrylamines, 1,2,3,4-tetrahydronaphthylamines (THNs), indanylamines, allylic and homoallylic amines, propargyl amines) was screened against the most versatile monoamine oxidase (MAO-N) variants D5, D9 and D11. MAO-N D9 exhibited the highest activity for most substrates and was applied to the deracemisation of a comprehensive set of selected primary amines. In all cases, excellent enantioselectivity was achieved (e.e. >99%) with moderate to good yields (55–80%). Conditions for the deracemisation of primary amines using a MAO-N/borane system were further optimised using THN as a template addressing substrate load, nature of the enzyme preparation, buffer systems, borane sources, and organic co-solvents.
CATALYTIC PREPARATION OF ENAMIDES FROM ALKYL AZIDES AND ACYL DONORS
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Paragraph 0076-0077, (2016/10/10)
The present invention relates to a method to synthesize an enamide compound by generating imine which does not have a substituent group bonded to the nitrogen from an organic azide compound and conducting a reaction of the same with acyl doner. By using t
Exploiting the Nucleophilicity of N-H Imines: Synthesis of Enamides from Alkyl Azides and Acid Anhydrides
Han, Junghoon,Jeon, Mina,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook
supporting information, p. 2769 - 2774 (2016/02/18)
The nucleophilicity of N-unsubstituted imines, which were generated from alkyl azides by a ruthenium-catalyzed reaction, was investigated in the reaction with acid anhydrides. The initial products were N-acylimines, which isomerized to the corresponding e
GOLD CATALYZED HYDROAMINATION OF ALKYNES AND ALLENES
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Page/Page column 21; 22, (2010/01/29)
Methods are provided for the catalytic hydroamination of compounds having an alkyne or allene functional group, in which the compound is contacted with ammonia or an amine in the presence of a catalytic amount of a gold complex under conditions sufficient for hydroamination to occur.
Homogeneous catalytic hydroamination of alkynes and allenes with ammonia
Lavallo, Vincent,Frey, Guido D.,Donnadieu, Bruno,Soleilhavoup, Michele,Bertrand, Guy
experimental part, p. 5224 - 5228 (2009/04/11)
(Chemical Equation Presented) A golden ticket to the synthesis of reactive nitrogen-containing compounds, such as imines, enamines, and allyl amines, through the addition of NH3 to unsaturated bonds is the cationic cyclic (alkyl)-(amino)carbene-gold(I) catalyst shown in blue (Dipp=diisopropylphenyl). An ideal initial step for the preparation of simple bulk chemicals, this reaction is also useful for the synthesis of more complex molecules (see examples).
THERMAL HETEROCYCLIZATION OF METHYL ARYL KETAZINES. III. REACTIONS OF THE TAUTOMERIC FORM OF THE AZINE
Shurukhin, Yu. V.,Klyuev, N. A.,Grandberg, I. I.
, p. 960 - 965 (2007/10/02)
The thermal reactions of methyl allyl ketazines (R= C6H5, 4-CH3C6H4, 4-CH3OC6H4, α-C10H7) in the region 320-350 deg C represent rearrangements to phthalazine and, to a lesser degree, indazole derivatives.The decomposition of these compounds and of the other cyclization products (pyridazines, pyrazoles, benzodiazepines), which determine the composition of the pyrolyzate at lower temperatures, leads to the formation of aromatic nitriles.This result rules out the formation of the latter by a mechanism of radical cleavage of the N-N bond in the azines of the aliphatic-aromatic series.A direct analogy was found between thermolysis and dissociative ionization, and this made it possible to predict the thermal reactions by means of mass-spectral data.
