54972-12-2

Usage

Uses

As demonstrated by Laszlo Kürti′s lab, ketomalonate oxime O-sulfonates act as doubly N-electrophilic linchpin reagents towards strong C-nucleophiles such as alkyl- and arylmetals (e.g., Grignard reagents). Thus, symmetrical dialkyl- as well as diarylamines may be directly prepared at low tempretatures and in the absence of transition metal catalysts. Other ketomalonate oxime O-sulfonates include 902918, 902705 and 902624.

Upstream product

• 42937-74-6 dimethyl 2-(hydroxyimino)malonate 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 72109-40-1 3-(toluene-4-sulfonyloxy)-3,5-dihydro-[1,2,3]triazole-4,4-dicarboxylic acid dimethyl ester 
• 90713-25-0 1-tosyloxy-4-methyl-5,5-bis(carbomethoxy)-Δ²-1,2,3-triazoline 
• 158615-45-3 5-Phenyl-3-(toluene-4-sulfonyloxy)-3,5-dihydro-[1,2,3]triazole-4,4-dicarboxylic acid dimethyl ester 
• 158615-44-2 5-Dimethoxymethyl-3-(toluene-4-sulfonyloxy)-3,5-dihydro-[1,2,3]triazole-4,4-dicarboxylic acid dimethyl ester 
• 90713-26-1 dimethyl α-tosyloxyamino-α-vinylmalonate 

Relevant academic research and scientific papers

PREPARATION OF SECONDARY AMINES WITH ELECTROPHILIC N-LINCHPIN REAGENTS

In one aspect, the present disclosure provides methods of preparing a secondary amine. In some embodiments, the secondary amine comprises two different groups or two identifical groups. Also provided herein are compositions for use in the preparation of the secondary amine.

Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation

Given the importance of amines in a large number of biologically active natural products, active pharmaceutical ingredients, agrochemicals, and functional materials, the development of efficient C-N bond-forming methods with wide substrate scope continues to be at the frontier of research in synthetic organic chemistry. Here, we present a general and fundamentally new synthetic approach for the direct, transition-metal-free preparation of symmetrical and unsymmetrical diaryl-, arylalkyl-, and dialkylamines that relies on the facile single or double addition of readily available C-nucleophiles to the nitrogen atom of bench-stable electrophilic aminating agents. Practical single and double polarity reversal (i.e., umpolung) of the nitrogen atom is achieved using sterically and electronically tunable ketomalonate-derived imines and oximes. Overall, this novel approach represents an operationally simple, scalable, and environmentally friendly alternative to transition-metal-catalyzed C-N cross-coupling methods that are currently used to access structurally diverse secondary amines.

New reactivity of oxaziridine: Pd(II)-catalyzed aromatic C-H ethoxycarbonylation via C-C bond cleavage

A novel Pd(II)-catalyzed aromatic C-H ethoxycarbonylation with oxaziridine involving C-C bond cleavage is described. Various aromatic 2-phenylpyridines and related compounds as well as aryl ureas can be effectively ethoxycarbonylated. A catalytic cycle in

Reaction of diaziridine-3,3-dicarboxylic acid dihydrazide with acetone

Using the reaction of diaziridine-3,3-dicarboxylic acid dihydrazide with acetone, new bicyclic diaziridines 7a,b have been obtained instead of expected tricyclic heterocycle 8.

SYNTHESE DE 1,2,3-TRIAZOLINES PAR CYCLOADDITION DIPOLAIRE-1,3 DE DIAZOALCANES A DES ESTERS D'OXIMES

Oximino-cyanacetic or malonesters 1, 2, 3 and 4 lead with diazoalcanes RCHN2 (R = H, CH3, Ph) to 1,2,3-triazolines.These triazolines present a low stability, however they are obtained crystallized with good yields.They are fully characterized and orientation of the cycloaddition is established.

1-ACYLOXYAZIRIDINE-2,2-DICARBOXYLIC ACID ESTERS

The reaction of diazomethane and O-acylisonitrosomalonates gave Δ2-1,2,3-triazoline-5,5-dicarboxylic acid esters, the rates of formation and thermal stabilities of which are determined by the character of this substituent attached to the oxygen