5704-08-5Relevant academic research and scientific papers
CATALYTIC PREPARATION OF ENAMIDES FROM ALKYL AZIDES AND ACYL DONORS
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Paragraph 0159-0160, (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
, 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
Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine
Munoz, Lourdes,Rodriguez, Anna M.,Rosell, Gloria,Bosch, M. Pilar,Guerrero, Angel
experimental part, p. 8171 - 8177 (2012/01/04)
Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used. The Royal Society of Chemistry 2011.
SYNTHESIS, TAUTOMERIZATION AND ACYLATION OF 1-PHENYLPROPANE-2-IMINES
Zielinski, W.,Mazik, M.
, p. 661 - 668 (2007/10/02)
1-Phenylpropane-2-imines and its derivatives substituted in a benzene ring were synthesized in reaction of proper ketones with ammonia.The keto-enol and imine-enamine tautomerisms in starting compounds and reaction products, respectively, were examined by proton nuclear magnetic resonance spectrometry and chemical methods.The determined constants of tautomeric equilibria were correlated with the Hammett ? constants.Electronic effects occurring in the systems under study were discussed basing on the correlations found.A possible use of 1-phenylpropane-2-imines in synthesis of N-acyl derivatives of 2-phenyl-1-methylvinylamines was examined.
Ligation and Reduction of Iron(III) Porphyrins by Amines. A Model for Cytochrome P-450 Monoamine Oxidase
Castro, C. E.,Jamin, Mary,Yokoyama, W.,Wade, Ruth
, p. 4179 - 4187 (2007/10/02)
The scope and mechanism of the ligation and reduction of iron(III) porphyrins by amines are presented.The reaction is general and proceeds with the overall stoichiometry 2PFe(III)Cl + 5RNH2 -> 2PFe(II)(H2NR)2 + R'CH=NH + 2RNH3(1+)Cl(1-).Imines are the only amine-derived products.The ability of the amine to coordinate iron and its possession of a >CHNH moiety are essential for reduction.The reaction path antails two successive reversible ligation steps followed by two one-electron reductions of the bis(amine)-ligated low-spin iron(III) adduct.In benzene the kinetics are biphasic.The second ligation is rate limiting 1(ligation > k(reduction) > k2(ligation)>.In dimethylformamide the first reduction step is rate limiting.The influence of nonreducing amines, porphyrin substituent, axial ligands, and deuteration of the substrate upon the kinetics leads to the formulation of the first reduction as a reversible outer-sphere electron transfer to the porphyrin periphery.This is followed by a rapid conversion of the generated aminium cation radical to an α-aminocarbinyl radical.The latter completes the reduction in an irreversible second step.The relevance of this chemistry to related transformation catalyzed by cytochrome P-450 is discussed.
