33417-03-7Relevant academic research and scientific papers
A facile synthesis of stable β-amino-N-/O-hemiacetals through a catalyst-free three-component Mannich-type reaction
Abonia, Rodrigo,Castillo, Juan C.,Garay, Alexander,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,D'Vries, Richard
supporting information, p. 1490 - 1494 (2017/03/23)
A practical, straightforward and one-step procedure for the synthesis of novel and stable β-amino-N-/O-hemiacetals (i.e. γ-aminoalcohols) is provided. The title compounds were obtained in good to excellent yields through an uncatalyzed three-component reaction by treatment of secondary amines with polyformaldehyde and electron-rich alkenes in acetonitrile as solvent at ambient temperature. The reactions proceeded with the formation of iminium ions, through a Mannich-type reaction, as the key intermediates for the generation of the target products. Single crystal X-ray analysis of derivative 4l confirmed unequivocally the structure and stability of the obtained compounds.
Factors influencing the regioselectivity of the oxidation of asymmetric secondary amines with singlet oxygen
Ushakov, Dmitry B.,Plutschack, Matthew B.,Gilmore, Kerry,Seeberger, Peter H.
supporting information, p. 6528 - 6534 (2015/04/22)
Aerobic amine oxidation is an attractive and elegant process for the α functionalization of amines. However, there are still several mechanistic uncertainties, particularly the factors governing the regioselectivity of the oxidation of asymmetric secondary amines and the oxidation rates of mixed primary amines. Herein, it is reported that singlet-oxygen-mediated oxidation of 1° and 2° amines is sensitive to the strength of the α-C-H bond and steric factors. Estimation of the relative bond dissociation energy by natural bond order analysis or by means of one-bond C-H coupling constants allowed the regioselectivity of secondary amine oxidations to be explained and predicted. In addition, the findings were utilized to synthesize highly regioselective substrates and perform selective amine cross-couplings to produce imines.
Application of sequential Cu(I)/Pd(0)-catalysis to solution-phase parallel synthesis of combinatorial libraries of dihydroindeno[1,2-c]isoquinolines
Kumar, Sarvesh,Painter, Thomas O.,Pal, Benoy K.,Neuenswander, Benjamin,Malinakova, Helena C.
scheme or table, p. 466 - 477 (2011/11/06)
Parallel solution-phase synthesis of combinatorial libraries of dihydroindenoisoquinolines employing a sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation protocol was realized. The scope and limitations of the protocol with respect to the substitution pattern in the aryl ring of the indene core, as well as the N-substituent have been defined, revealing that the methodology is compatible with a wide-range of aliphatic linear, branched, and ester functionalized N-substituents. Unexpectedly, the formation of regioisomers featuring a 1,2,3-contiguous substitution pattern in the aromatic ring of the indene core was observed. Three distinct combinatorial libraries with a total of 111 of members were synthesized, and 80 highly substituted dihydroindenoisoquinolines structurally related to known medicinal agents including some consisting of mixtures of two regioisomers were made available for biological activity testing.
Catalytic, asymmetric Strecker reactions catalysed by titaniumIV and vanadiumV(salen) complexes
Blacker, John,Clutterbuck, Lisa A.,Crampton, Michael R.,Grosjean, Christophe,North, Michael
, p. 1449 - 1456 (2007/10/03)
VanadiumV(salen) complex 3 has been found to be an effective catalyst for the asymmetric addition of hydrogen cyanide (generated in situ from trimethylsilyl cyanide) to imines. The best results (up to 81% enantiomeric excess) were obtained for aromatic imines in which the nitrogen atom is protected with a benzyl group and in which the imine bond is not sterically encumbered.
Phosphatase inhibitors. III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase
Beers, Scott A.,Schwender, Charles F.,Loughney, Deborah A.,Malloy, Elizabeth,Demarest, Keith,Jordan, Jerold
, p. 1693 - 1701 (2007/10/03)
Further investigation of the structural requirements of a series of benzylphosphonic acid inhibitors of human prostatic acid phosphatase has led to the highly potent series of α-aminobenzylphosphonic acids. The α-benzylaminobenzylphosphonic acid, with an IC50 = 4 nM, exhibited a 3500-fold improvement in potency over the carbon analogue, α-phenylethyl. The enhanced potency may be due to a combination of four favorable interactions including those with the phosphate binding region, the presence the hydrophobic moieties of the benzylamino and phenylphosphonic acid, and a rigid conformer produced by an internal salt bridge between the phosphonate and the α-amino group. Replacement of the phosphonic acid moiety with a phosphinic or carboxylic acid as well as deletion of the benzyl substitution on the α-amino group led to great reductions in potency.
