64384-47-0Relevant academic research and scientific papers
Primary α-tertiary amine synthesis via α-C-H functionalization
Vasu, Dhananjayan,Fuentes de Arriba, Angel L.,Leitch, Jamie A.,De Gombert, Antoine,Dixon, Darren J.
, p. 3401 - 3407 (2019/03/21)
A quinone-mediated general synthetic platform for the construction of primary α-tertiary amines from abundant primary α-branched amine starting materials is described. This procedure pivots on the efficient in situ generation of reactive ketimine intermediates and subsequent reaction with carbon-centered nucleophiles such as organomagnesium and organolithium reagents, and TMSCN, creating quaternary centers. Furthermore, extension to reverse polarity photoredox catalysis enables reactivity with electrophiles, via a nucleophilic α-amino radical intermediate. This efficient, broadly applicable and scalable amine-to-amine synthetic platform was successfully applied to library and API synthesis and in the functionalization of drug molecules.
High-yielding automated convergent synthesis of no-carrier-added [11C-carbonyl]-labeled amino acids using the strecker reaction
Xing, Junhao,Brooks, Allen F.,Fink, Dylan,Zhang, Huibin,Piert, Morand R.,Scott, Peter J.H.,Shao, Xia
supporting information, p. 371 - 375 (2017/02/10)
A new variant of the Strecker synthesis using no-carrier-added [11C]cyanide for the synthesis of radiolabeled amino acids is described. The protocol is fully automated using a radiochemistry synthesis module and applied to the production of a number of new PET radiotracers. [11C-Carbonyl]sarcosine, [11C-carbonyl]methionine, [11C-carbonyl]-N-phenylglycine, and [11C-carbonyl]glycine are all synthesized in moderate to good radiochemical yields. The synthesis of [11C-carbon-yl]sarcosine has been validated for production of doses for clinical use, and preliminary evaluation of the new radiotracer in PC3 tumor-bearing mice is also reported.
Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl) imidazolidine-4-one ligands
Drabina, Pavel,Karel, Sergej,Panov, Illia,Sedlak, Milos
, p. 334 - 339 (2013/04/23)
Currently, asymmetric synthesis represents one of the main streams of organic synthesis. Although an extensive research has been carried out in this area, the synthesis of chiral compounds with the required enantiomeric purity is still a challenging issue. Herein, we focus on the preparation of new enantioselective catalysts based on pyridine-imidazolidinones. The substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-ones 5-8 were prepared by condensation of chiral amino acid amides (α-methylDOPA and α- methylphenylalanine) with 2-acetylpyridine and pyridine-2-carbaldehyde. The individual isomers of the described ligands 5-8 were separated chromatographically. The copper(II) complexes of these chiral ligands were studied as enantioselective catalysts for the asymmetric Henry reaction of substituted aldehydes with nitromethane or nitroethane. The ligands containing a methyl group at the 2-position of the imidazolidinone ring 6a and 8a exhibit a high degree of enantioselectivity (up to 91% ee). The nitroaldols derived from nitroethane (2-nitropropan-1-ols) were obtained with a comparable enantiomeric purity to derivatives of 2-nitroethanol. This group of ligands represents a new and promising class of enantioselective catalysts, which deserve further attention.
Versatile synthesis of free and N-benzyloxycarbonyl-protected 2,2-disubstituted taurines
Wang, Boyuan,Zhang, Wei,Zhang, Leilei,Du, Da-Ming,Liu, Gang,Xu, Jiaxi
, p. 350 - 355 (2008/09/18)
An effective and versatile method was developed to synthesize N-benzyloxycarbonyl-protected and free 2,2-disubstituted taurines. Several novel 2,2-disubstituted taurines, including aliphatic/aromatic and cyclic/acyclic derivatives, were obtained, which demonstrates the generality of this method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Synthesis and Antitumor Activity of Pt(II) Complexes of Benzyl-1,2-diaminoethane Ligands
Brunner, Henri,Hankofer, Peter,Treittinger, Barbara
, p. 1029 - 1038 (2007/10/02)
Twelve new diamine ligands are synthesized and characterized in which a benzyl group and another vicinal substituent or a benzyl group, a 4-Cl-benzyl group, and a 4-MeO-benzyl group, respectively, and two other geminal substituents are attached to the 1,2
