Synthèse et amination réductrice de phosphonopyruvates: préparation d'acides amino-2 carboxy-2 alkylphosphoniques (β-phosphonoalanine)

1979 ◽  
Vol 57 (24) ◽  
pp. 3216-3220 ◽  
Author(s):  
Jean-Marie Varlet ◽  
Noël Collignon ◽  
Philippe Savignac
Keyword(s):  
Amino Acids ◽  
Reductive Amination ◽  
Primary Amines ◽  
Amino Esters

The reaction of α-copper(I)alkanephosphonates with methyl and ethyl oxalyl chlorides gives methyl or ethyl dialkylphosphonopyruvates which, submitted to reductive amination in ethanol at pH 6–7 with sodium cyanohydridoborate (NaBH3CN) and ammonia, or primary amines, lead to phosphonic amino esters; hydrolysis with diluted HCl gives phosphonic amino acids. These three reactions constitute a general way to β-phosphonoalanine and β-alkyl β-phosphonoalanine.

Aminobenzylation d'aldéhydes phosphoniques: préparation d'acides aminoalkylphosphoniques

1981 ◽  
Vol 59 (19) ◽  
pp. 2864-2869 ◽  
Author(s):  
Geneviève Fabre ◽  
Noël Collignon ◽  
Philippe Savignac
Keyword(s):  
Amino Acids ◽  
Catalytic Hydrogenation ◽  
Reductive Amination ◽  
Reducing Agent ◽  
Amino Esters ◽  
Hydrolysis Of

The reaction of phosphonic aldehydes with benzylamine in presence of NaBH3CN yields benzylaminoalkylphosphonates which, submitted to catalytic hydrogenation, lead to phosphonic amino esters. When reductive amination is carried out with H2/Pd reduction and debenzylation are observed simultaneously. In the absence of reducing agent the enaminobenzylphosphonate can be isolated and N-alkylated. Hydrolysis of phosphonic amino-esters with dilute HCl gives phosphonic amino acids. The order of occurrence of each operation, as well as the choice of the catalyst is discussed.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Synthesis ◽  
2021 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Petr Beier ◽  
Maryam Khalili Foumeshi ◽  
Ali Alaei ◽  
Blanka Klepetářová
Keyword(s):  
Amino Acids ◽  
Carbon Disulfide ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Primary Amines ◽  
Oxidation Reactions ◽  
Michael Addition Reaction ◽  
Synthetic Utility ◽  
Reaction Proceeds

AbstractThiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

A general metal-free route towards the synthesis of 1,2,3-triazoles from readily available primary amines and ketones

2016 ◽  
Vol 52 (14) ◽  
pp. 2885-2888 ◽  
Author(s):  
Joice Thomas ◽  
Sampad Jana ◽  
Jubi John ◽  
Sandra Liekens ◽  
Wim Dehaen
Keyword(s):  
Natural Products ◽  
Primary Amines ◽  
Metal Free ◽  
Amino Esters

A metal-free route towards different 1,2,3-triazole heterocycles was accomplished by using inexpensive and readily available ketones and primary amines. This reaction is very general and was extended to functionalize different amino esters, dendrimers and natural products.

Primary Amines by Transfer Hydrogenative Reductive Amination of Ketones by Using Cyclometalated IrIIICatalysts

2013 ◽  
Vol 20 (1) ◽  
pp. 245-252 ◽  
Author(s):  
Dinesh Talwar ◽  
Noemí Poyatos Salguero ◽  
Craig M. Robertson ◽  
Jianliang Xiao
Keyword(s):  
Reductive Amination ◽  
Primary Amines

Ambient-Temperature Synthesis of Primary Amines via Reductive Amination of Carbonyl Compounds

ACS Catalysis ◽  
2020 ◽  
Vol 10 (14) ◽  
pp. 7763-7772 ◽  
Author(s):  
Chao Xie ◽  
Jinliang Song ◽  
Manli Hua ◽  
Yue Hu ◽  
Xin Huang ◽  
...  
Keyword(s):  
Ambient Temperature ◽  
Carbonyl Compounds ◽  
Reductive Amination ◽  
Primary Amines ◽  
Temperature Synthesis

Titration syntheses of polyaminosubstituted phthalocyanines via nucleophilic aromatic substitutions on zinc(II) 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecafluorophthalocyanine

2007 ◽  
Vol 11 (07) ◽  
pp. 537-546 ◽  
Author(s):  
Clifford C. Leznoff ◽  
Annette Hiebert ◽  
Sibel Ok
Keyword(s):  
Amino Acids ◽  
Chain Length ◽  
Secondary Amines ◽  
Primary Amines ◽  
Tertiary Butyl ◽  
Butyl Esters ◽  
Mild Conditions ◽  
Nucleophilic Aromatic Substitutions

Primary amines, secondary amines and tertiary butyl esters of amino acids are used as nucleophiles with zinc(II) hexadecafluorophthalocyanine to provide mixtures of mono and disubstituted fluorinated phthalocyanines under mild conditions, or polyaminosubstituted phthalocyanines when using the amines as solvents. Diamines give cyclic substituted phthalocyanines, binuclear or trinuclear phthalocyanines or mixtures of both types, depending on the chain length or structure of the diamine.

Selective Synthesis of Primary Amines by Reductive Amination of Ketones with Ammonia over Supported Pt catalysts

ChemCatChem ◽  
2015 ◽  
Vol 7 (6) ◽  
pp. 921-924 ◽  
Author(s):  
Yoichi Nakamura ◽  
Kenichi Kon ◽  
Abeda Sultana Touchy ◽  
Ken-ichi Shimizu ◽  
Wataru Ueda
Keyword(s):  
Reductive Amination ◽  
Primary Amines ◽  
Selective Synthesis ◽  
Pt Catalysts ◽  
Supported Pt Catalysts

scholarly journals Straightforward synthesis of enantiomerically pure 1,2,3-triazoles derived from amino esters

2018 ◽  
Vol 16 (17) ◽  
pp. 3168-3176 ◽  
Author(s):  
Gastón Silveira-Dorta ◽  
Sampad Jana ◽  
Lucie Borkova ◽  
Joice Thomas ◽  
Wim Dehaen
Keyword(s):  
Amino Acids ◽  
Enantiomerically Pure ◽  
Triazole Derivatives ◽  
Amino Esters ◽  
Good Yielding ◽  
Derivatives Of

An easy, good-yielding access to functionalized enantiomerically pure 1,2,3-triazole derivatives of amino acids using commercially available ketones and amino esters is described.

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