10344-69-1

Usage

Uses

Used in Catalyst Preparation:
DIETHYL MALONIMIDATE DIHYDROCHLORIDE is used as a reactant for the preparation of rhenium cyanobis(oxazoline) oxo complexes, which act as enantioselective reduction catalysts. These catalysts are crucial in the field of asymmetric synthesis, enabling the selective formation of specific enantiomers in chemical reactions.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, DIETHYL MALONIMIDATE DIHYDROCHLORIDE is used as a reactant for the synthesis of chiral bis(oxazoline)-copper complexes. These complexes are immobilized by donor-acceptor interactions on insoluble organic supports, making them reusable catalysts for asymmetric Diels-Alder cycloaddition reactions. This application is significant in the production of enantiomerically pure compounds, which are essential in pharmaceuticals and agrochemicals.
Used in Enantioselective Transfer Hydrogenation:
DIETHYL MALONIMIDATE DIHYDROCHLORIDE is also used in the preparation of nonracemic bis(oxazoline)ruthenium p-cymene complexes and their silica-supported analogs. These complexes serve as catalysts for the enantioselective transfer hydrogenation of ketones to secondary alcohols. This process is vital in the synthesis of optically active alcohols, which are widely used in the pharmaceutical and chemical industries.
Overall, DIETHYL MALONIMIDATE DIHYDROCHLORIDE plays a crucial role in the development of enantioselective catalysts and complexes, which are essential in various chemical reactions and industries. Its ability to form stable donor-acceptor interactions makes it a valuable component in the synthesis of chiral catalysts, contributing to the advancement of asymmetric synthesis and enantioselective processes.

InChI:InChI=1/C7H13NO3/c1-3-10-6(8)5-7(9)11-4-2/h8H,3-5H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 109-77-3 malononitrile 

Downstream Products

• 7597-56-0 ethyl malonamate 
• 42003-88-3 ethyl 2-cyanoacetimidate 
• 105-53-3 diethyl malonate 
• 75-00-3 chloroethane 
• 108-13-4 malonodiamide 
• 107303-15-1 N,N',N',N''-Tetraphenaethyl-malonsaeure-diamidin 
• 131833-90-4 2,2'-methylenebis[(4S)-4-isopropyl-4,5-dihydro-oxazole] 
• 132098-58-9 2,2'-methylenebis[(4S)-4-benzyl-4,5-dihydro-2-oxazole] 
• 133463-87-3 (-)-(4S,4'S,5S,5'S)-4,4',5,5'-Tetrahydro-2,2'-methylene-5,5'-diphenylbis-4,4'-di(methanol) 
• 132098-59-0 (S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline) 
• 132098-54-5 (S,S)-2,2'-methylenebis(4-tert-butyl-2-oxazoline) 
• 26315-24-2 Malondiimidsaeure-diethylester 
• 164976-63-0 2,2'-methylenebis[(4S)-4-isopropyl-2-oxazoline] 
• 131833-91-5 2,2-methylene-[(4R)-3,5-tert-butylphenyl-2-oxazoline] 

Relevant academic research and scientific papers

CuII/TEMPO-Catalyzed Enantioselective C(sp3)–H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation

A novel strategy for asymmetric Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochemistry, affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.

Intramolecular Imidazole-Promoted General-Base Catalysis of the Hydrolysis of an Acetylimidazole

Intramolecular general-base catalysis of the hydrolysis of an acetylimidazole by imidazole is assessed by studying the hydrolysis of 2-(imidazol-2-ylmethyl)-N-acetylimidazole (3).The pH vs. log kobsd profile exhibits three major domains that consist of H2O attack on the protonated acetylimidazolium unit,OH- attack on the neutral material, and an intramolecular general-base catalysis of H2O on the neutral species.Consistent with the latter is a plateau observed in the pH profile (k3 = 1.02*10-3 s-1) at neutrality and a solvent kinetic isotope effect of kH2O/kD2O = 2.8 in that region.The effective molarity of the intramolecular imidazole in 3 can be assessed by comparing the value of k3 with the second-order rate constant for 2-methylimidazole catalyzing the hydrolysis of 2-methyl-N-acetylimidazole (4).After the difference in the imidazole pKa values is corrected for, the effective molarity of the intramolecular catalyst is 3 M.

Synthesis of C2-symmetric bisamidines: A new type of chiral metal-free lewis acid analogue interacting with carbonyl groups

(Chemical Equation Presented) The chiral bisamidine 5 has been prepared in just two steps from malonodinitrile. In the monocationic form this compound adopts a planar conformation with an almost convergent orientation of two N-H groups. Ketones, aldehydes

Analogs of biologically active compounds IX.1 Synthesis of several new uracil and pteridine 6-azaanalogs based on cyclization of arylhydrazones derived from mesoxalic acid

A series of 5C and 5N substituted 3-oxo-2-phenyl-1,2,4-triazine-6-carbonitriles and 8-imino-2-arylpyrimido[4,5-e][1,2,4]triazine-3,6(2H,5H)-diones (6-aryl-6-azapteridines) are described via a cyclocondensation reaction from the corresponding aryliminohydrazones with CDI. The required aryliminohydrazones were obtained from the starting compound – malononitrile. These prepared compounds were tested for cytotoxic activity on cancer cell lines.

PROCESS FOR SYNTHESIS OF PICOLINAMIDES

The present technology relates to processes, mixtures and intermediates useful for making picolinamide fungicides. The picolinamide compounds are prepared by processes that include coupling together a 4-methoxy-3-acyloxypicolinic acid with key 2-amino-L-alaninate esters derived from substituted 2-phenylethanols.

Copper-Nitrene-Catalyzed Desymmetric Oxaziridination/1,2-Alkyl Rearrangement of 1,3-Diketones toward Bicyclic Lactams

Although copper-nitrene has been extensively studied as a versatile active species in various transformations, asymmetric reactions involving copper-nitrene have been limited to the aziridination of olefins. Herein, we report the novel copper-nitrene-catalyzed desymmetric oxaziridination reaction of cyclic diketones with alkyl azides and the subsequent rearrangement of the resulting highly active intermediate, which produces a synthetically challenging chiral bicyclic lactam containing a quaternary carbon center. This procedure not only enriches the copper-nitrene-catalyzed asymmetric reactions, but also provides an alternative strategy to address the inherent challenges of catalytic asymmetric Schmidt reactions. This unique reaction could inspire the investigation of novel copper-nitrene-catalyzed asymmetric transformations and their reaction mechanisms.

Enantioselective Synthesis of N-Benzylic Heterocycles: A Nickel and Photoredox Dual Catalysis Approach

Reported herein is a dual nickel- and photoredox-catalyzed modular approach for the preparation of enantioenriched N-benzylic heterocycles. α-Heterocyclic carboxylic acids, easily obtainable from common commercial material, are reported as suitable substrates for a decarboxylative strategy in conjunction with a chiral pyridine-oxazoline (PyOx) ligand, providing quick access to enantioenriched drug-like products. The presence of a directing group on the heterocyclic moiety is shown to be beneficial, affording improved stereoselectivity in a number of cases.

Modular ligand variation in calcium bisimidazoline complexes: Effects on ligand redistribution and hydroamination catalysis

A series of calcium complexes supported by chiral bisimidazoline ligands have been studied in the catalytic intramolecular hydroamination/cyclisation of amino-olefins. The complexes [Ca(R-BIM){N(SiMe3)2}(THF)] (R = 4-C6Hs

Spectroscopic studies on complexes of magnesium (II) with C2-chiral bis-oxazolines

The configurations of chloro, ethyl and bis-complexes of magnesium with C2-chiral bis-oxazolines such as 2,2′-methylenebis[(4S)-4-iso-propyl-2-oxazoline] (MBIO). 2,2′-methylenebis[(4S)-4-tert-butyl-2-oxazoline] (MBTO) and 2,2′-methylenebis[(4S)-4-phenyl-2-oxazoline] (MBPO) have been investigated on the basis of spectroscopic studies. The IR and NMR (1H, 13C) data suggested that the bis-oxazoline ligands coordinated magnesium (II) through both the nitrogen atoms. The molecular weight determination in nitrobenzene indicated the dimeric nature of chloro and ethylmagnesium complexes whereas bis-magnesium complexes were found to be monomeric.

Thiono and Dithio Esters, 40. - Reactions of Dithionomalonic Esters with Nucleophilic Nitrogen Bases

Dithionomalonic esters 1, obtained from malonitrile via malonodiimidium salts 5 by thiolysis, react with amines under elimination of H2S to form the 3-amino-thioacrylic O-esters 11.The alkali salts of 1 condense with amines to give the malonodithioamides 12 by loss of 2 molecules of alcohol.Oxidative cyclization of 11 leads to the isothiazoles 16-18.Reaction of 1 with hydrazines gives rise to the pyrazoles 20-22; with amidines the pyrimidines 23 and 24 were obtained.