3319-00-4Relevant academic research and scientific papers
Ruthenium-catalyzed /V-alkylation of amines and sulfonamides using borrowing hydrogen methodology
Hamid, M. Haniti S. A.,Allen, C. Liana,Lamb, Gareth W.,Maxwell, Aoife C.,Maytum, Hannah C.,et al.
supporting information; experimental part, p. 1766 - 1774 (2009/07/25)
The alkylation of amines by alcohols has been achieved using 0.5 mol percent [Ru(p-cymene)CI2]2 with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. A/-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols requiremore forcing conditions than primary alcohols but are still effective a lkylating agents in the presence of this catalyst.
Preparation of non-racemic single-stereocentre α-aminonitriles and a study of their fate in Bruylants reactions
Beaufort-Droal, Virginie,Pereira, Elisabeth,Théry, Vincent,Aitken, David J.
, p. 11948 - 11954 (2007/10/03)
A number of chiral carboxamide dehydration methods were investigated for the preparation of four representative enantiomerically enriched α-aminonitriles possessing only one stereogenic centre; best results were observed using Burgess' salt (yield up to 87%, er up to 92/8) or the trifluoroacetic anhydride-triethylamine combination (yield up to 98%, er up to 86/14). Two of the aminonitriles thus obtained were subjected to Bruylants reactions with a methyl Grignard reagent to furnish the corresponding tertiary amines; these products, along with any unreacted starting materials, were obtained essentially in racemic form. In accord with the accepted mechanism for this reaction, a magnesium species is implicated in the formation of an iminium, the common intermediate for both chemical transformation and racemization processes.
A base-catalyzed domino-isomerization-hydroamination reaction - A new synthetic route to amphetamines
Hartung, Christian G.,Breindl, Claudia,Tillack, Annegret,Beller, Matthias
, p. 5157 - 5162 (2007/10/03)
An efficient synthesis of pharmaceutically interesting amphetamines by a base-catalyzed domino-isomerization- hydroamination reaction is presented. Starting from allylbenzene and various primary or secondary amines, the basic structural pattern of amphetamines is synthesized directly in yields of up to 91% in the presence of catalytic amounts of n-butyllithium. (C) 2000 Elsevier Science Ltd.
Synthesis of β-phenylethylamines from styrene derivatives
Seijas, Julio A.,Vazquez-Tato, M. Pilar,Entenza, Cesar,Martinez, M. Montserrat,Onega, M. Gabriela,Veiga, Susana
, p. 5073 - 5076 (2007/10/03)
β-Phenylethylamines are prepared from the styrene derivatives; 4,4- dimethyl-2-(2-vinylphenyl)-2-oxazoline, 2-(3-methoxy-2-vinylpnenyl)-4,4- dimethyl-2-oxazoline, 2-vinylbenzoic acid, styrene, β-methylstyrene, and α- methylstyrene.
