Journal ArticleDOI
Cesium effect: high chemoselectivity in direct N-alkylation of amines
TLDR
The results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation, offering wide applications in peptidomimetic syntheses.Abstract:
A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the secondary amines exclusively, offering wide applications in peptidomimetic syntheses.read more
Citations
More filters
Journal ArticleDOI
Synthesis of new ionic liquids from α-, β-alanine and α-iodo ketones
TL;DR: The one-pot reaction of α-, β-alanine with 1-iodopropan-2-one, 2-iodo-1-phenylethanone and 2-Iodo-1-(2-thienyl)-ethanone and elemental iodine proceeds without solvents and basic media to afford a novel family of ionic liquids with triiodide counteranion as discussed by the authors.
DissertationDOI
Novel SMAC Mimetics as Peptide-based Small Molecule Inhibitors of IAPs to Induce Apoptosis in Cancer Cells
Journal ArticleDOI
2-Hy-droxy-N-(4-meth-oxy-benz-yl)-4-nitro-anilinium chloride.
TL;DR: The crystal structure of the title compound, C14H15N2O4 +·Cl−, can be described as being composed of layers containing both cations and anions that are staggered along, and two types of the hydrogen bonds are observed, viz. cation–anion and cation-cation.
Patent
Photoinduced signal amplification through externally sensitized photofragmentation in masked photosensitizers and photoamplified fluorescence turn-off system
TL;DR: In this article, a photoamplified fluorescence turn-off assay where a masked photosensitizer is mixed with a fluorescent molecule is presented, and the mixture is brightly fluorescent because the masked photosensor is not capable of quenching the fluorophore.
Journal ArticleDOI
An efficient transition-metal-free route to oligo-α-pyridylamines via fluoroarenes
TL;DR: The polynucleating tripodal proligand H 6 tren(dpa) 3 , containing thirteen nitrogen donors of four different types, was designed, synthesized, and isolated in good yield (∼60%) via a transition-metal-free triple N-arylation of H6 tren with HXdpa as mentioned in this paper .
References
More filters
Book
Reagents for Organic Synthesis
TL;DR: In this paper, the authors propose a method for using Reference Abbreviations (RABs) as a reference abbreviation for reference abbreviations in the context of bioinformatics.
Journal ArticleDOI
Synthesis of secondary amines
Journal ArticleDOI
An assessment of the causes of the cesium effect
TL;DR: In this paper, the effect of this effect on macrocyclization by means of nucleophilic substitution is discussed. But it is concluded that the cesium ion is virtually completely solvated and that carboxylates are essentially free and highly reactive.