Synthesis Of Dialkyl Research Articles

Recent Advances in the Synthesis of Dialkyl (Aryl) α-(Aryl/Heterocyclic/Heteroaryl- α-(Aryl/Heteroarylamino)Phosphonates

Abstract: This review describes recent advances that are commonly applied in the synthesis of dialkyl (aryl) α-aminophosphonates containing heterocyclic compounds. The target structures are divided into three categories, which include α-aminophosphonic acids and their diesters bearing a heterocyclic or heteroaryl system at the α-carbon, nitrogen atom, or both. The synthetic protocols based on the Kabachnik-Fields and Pudovik reactions as the main pathways for the construction of these features, besides other miscellaneous methods. This review may be a useful resource for researchers and it will help them to work in this emerging research area.

Synthesis of Oil Soluble Boron Esters and Obtaining Lubricant Additive Packages with Anti-wear and Extreme Pressure Properties

The purpose of this work is synthesis and characterization of pryridin-yl-borate esters and investigation of tribological performance as additive. The syn-thesis of dialkyl-(2-(pyridin-2-yl) ethyl) borate esters both in the literature and the novel synthesis of dialkyl 2-(methyl (pyridin-2-yl) borate esters and dialkyl 2- (5-ethylpyridin-2-yl) ethyl borate esters were carried out. The boron esters to be obtained were characterized by using IR, 1H NMR,13C NMR spectroscopic methods as well as physical methods such as TAN and corrosion tests. The fric-tion-reducing and anti-wear properties of the synthesized lubricant additives were measured with a four-ball friction and wear tester. As a result of these stud-ies, it has been shown that the friction coefficient is reduced by about 30-40 % compared to the base oil and the wear is also reduced. In the tribological analysis performed using synthesized four molecules within the scope of the study, it was found that resistance to oxidation is increased when the synthesized molecules were added to group I base oil at 0.5 % and 1% w/w concentration. The novel synthesis of dialkyl 2-(methyl (pyridin-2-yl) borate esters and dialkyl 2- (5-ethylpyridin-2-yl) ethyl borate esters were carried out and tribological perfor-mances in base oil were analysed first time.

Hybrid Quinolinyl Phosphonates as Heterocyclic Carboxylate Isosteres: Synthesis and Biological Evaluation against Topoisomerase 1B (TOP1B).

This work describes, for the first time, the synthesis of dialkyl (2-arylquinolin-8-yl)phosphonate derivatives. The preparation was carried out through a direct and simple process as a multicomponent Povarov reaction of aminophenylphosphonates, aldehydes, and styrenes and subsequent oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or, alternatively, by a cycloaddition reaction between phosphonate aldimines and acetylenes. Based on phosphonate group structural characteristics, considered as phosphorous isosteres of carboxylic heterocycles, they may present interesting biological properties related to cell proliferation. In the current report, a new series of dialkyl (2-arylquinolin-8-yl)phosphonates have been synthesized and their antiproliferative effect evaluated on different human cancer and embryonic cells, as well as on Leishmania infantum parasites, a eukaryotic protist responsible for visceral leishmaniasis. Thereby, the antitumor effect was assessed in human lung adenocarcinoma cells (A549), human ovarian carcinoma cells (SKOV3), and human embryonic kidney cells (HEK293) versus the non-cancerous lung fibroblasts cell line (MRC5). On the other hand, the antileishmanial activity was tested against both stages of L. infantum cell cycle, namely free-living promastigotes and intramacrophage amastigotes, using a primary culture of Balb/c splenocytes to calculate the selectivity index. Besides the antiproliferative and antileishmanial capacities, their behavior as topoisomerase 1B inhibitors has been evaluated as a possible mechanism of action.

Synthesis of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophthalates and Their Sulfonylation

Dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate and dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate were obtained in the free form for the first time. The products were sulfonylated with p-toluenesulfonyl to obtain previously unknown dialkyl 5-(4-toluenesulfonamido)-2-hydroxy-4,6-dimethylisophthalates. The use of p-acetamidobenzenesulfonyl chloride as the sulfonylating agent in this reaction led to the formation of dialkyl 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethyl isophthalates. The synthesized sulfonamide derivatives are of interest as potentially biologically active compounds. The structure of all the obtained compounds was proved using IR and NMR spectroscopy and mass spectrometry.

A Convenient Synthesis of Fused Tetrahydroazocines from Acenaphthylene-1,2-dione, Proline, and Acetylenic Esters

A synthesis of dialkyl (12E,14E)-7-oxo-10,11-dihydro-7H,9H-azocino[2,1-a]benzo[de]isoquinoline-13,14-dicarboxylates through a 1,3-dipolar cycloaddition reaction of azomethine ylides, generated in situ from proline and acenaphthylene-1,2-dione, with dialkyl acetylenedicarboxylates is described. According to the X-ray diffraction data, the tetrahydroazocine ring has a rigid twist-boat form with approximate local C2 symmetry.

Microwave-assisted synthesis of dialkyl ω-azidoalkylphosphonates

ABSTRACTAn efficient and reproducible microwave-assisted synthesis of dialkyl ω-azidoalkylphosphonates via nucleophilic substitution of the appropriate dialkyl ω-bromoalkylphosphonates by sodium azide in water or dimethylformamide (DMF) as solvent has been developed. This process has been optimized for batch reactors. The target, structurally diverse dialkyl ω-azidoalkylphosphonates with different steric hindrance around the phosphonato groups and containing unbranched side carbon chains of different lengths (n = 2–6), has been obtained in moderate to high yields (39–87%).

Three-Component Reaction of Alkyl Isocyanide, Acetylenic Diesters and 5-Hydroxy-5- Arylpyrimidine-2,4,6(1H,3H,5H)-Trione

A three-component reaction of an alkyl isocyanide, an acetylenic diester and 5-hydroxy-5-arylpyrimidine-2,4,6(1H,3H,5H)-trione provides an efficient route for the synthesis of dialkyl 2-(alkylamino)-5-(4-nitrophenyl)-7,9,11-trioxo-1-oxa-5,8,10-triazaspiro[5.5]undec-2-ene-3,4-dicarboxylate derivatives.

Synthesis of dialkyl 2-(Methacryloyloxyethyl) phosphonates, their characterization and polymerization

Dimethyl and diethyl 2-(methacryloyloxyethyl) phosphonates were synthesized using the Michaelis-Becker reaction. This method of phosphonate preparation is advantageous over the acid chloride route in terms of mild reaction condition and by employing non-corrosive, moisture insensitive reagents. These phosphonates were characterized by mass spectrometry, Fourier Transform Infrared and Nuclear Magnetic Resonance spectroscopic methods. The kinetics for the bulk polymerization of dialkylmethacryloyloxyethyl phosphonates were followed by Differential Scanning Calorimetry. Activation energy was calculated using Ozawa and Kissinger methods and was found to be in the range of 60–75 kJ/mol. Thermogravimetric analysis of polymerized samples showed two-step degradation in nitrogen atmosphere.

New synthesis of dialkyl (E/Z)-(1-arylethylidene)aminooxy phosphonates by the reaction of oximes and trialkylphosphites in the presence of diisopropyl azodicarboxylate

The reaction between trialkylphosphites and diisopropyl azodicarboxylates in the presence of ketoxime leads to dialkyl (1-arylethylidene)aminooxy phosphonate isomers with (E/Z) geometry.

ChemInform Abstract: Synthesis of Dialkyl {(Aryl)[2,2‐dimethyl‐4‐oxo‐6‐(piperidin‐1‐yl)‐4H‐ [1,3]dioxin‐5‐yl]methyl}phosphonate by Reaction of Meldrum′s Acid, Aryl Aldehydes and Trialkyl Phosphites in the Presence of Piperidine.

ChemInform Abstract: Synthesis of Dialkyl {(Aryl)[2,2‐dimethyl‐4‐oxo‐6‐(piperidin‐1‐yl)‐4H‐ [1,3]dioxin‐5‐yl]methyl}phosphonate by Reaction of Meldrum′s Acid, Aryl Aldehydes and Trialkyl Phosphites in the Presence of Piperidine.

ChemInform Abstract: 2‐Chloro‐3,3,5‐trimethyl‐2,3‐dihydro‐1,2λ 5‐oxaphosphole 2‐Oxide as Precursor in a New Synthesis of Dialkyl(diaryl)(2‐methyl‐4‐oxopent‐2‐yl)phosphine Oxides.

ChemInform Abstract: 2‐Chloro‐3,3,5‐trimethyl‐2,3‐dihydro‐1,2λ ⁵‐oxaphosphole 2‐Oxide as Precursor in a New Synthesis of Dialkyl(diaryl)(2‐methyl‐4‐oxopent‐2‐yl)phosphine Oxides.

Synthesis of Dialkyl {(aryl)[2,2-Dimethyl-4-oxo-6-(Piperidin-1-yl)-4H-[1,3]Dioxin-5-yl]Methyl}Phosphonate by Reaction of Meldrum's Acid, Aryl Aldehydes and Trialkyl Phosphites in the Presence of Piperidine

A four-component reaction between Meldrum's acid, aryl aldehydes with trialkyl phosphites in the presence of piper-idine has been developed. The reaction affords dialkyl {(aryl)[2,2-dimethyl-4-oxo-6-(piperidin-1-yl)-4 H-[1,3]dioxin-5-yl]methyl}phosphonate in moderate to good yields in a one-pot process.

ChemInform Abstract: Synthesis of Dialkyl and Diaryl Benzylphosphonates Through a ZnI2‐Mediated Reaction.

AbstractThe spectrum of phosphite substrates used also includes hindered and optically active ones.

Synthesis of dialkyl and diaryl benzylphosphonates through a ZnI2-mediated reaction

Several trialkyl and two triaryl phosphites have been tested for their reactivity in the zinc iodide mediated conversion of benzyl alcohol to the corresponding phosphonates. Most react smoothly to afford the desired phosphonate diesters, including hindered and nonracemic phosphites. The implications of this reactivity on the reactions involved in the transformation are discussed.

ChemInform Abstract: Heterocyclizations of Functionalized Heterocumulenes with C,N‐, C,O‐, and C,S‐Binucleophiles. Part 13. Synthesis of Dialkyl 2‐Oxo‐3‐allyl‐1,2,3,6‐tetrahydropyrimidine‐4,5‐dicarboxylates (III) and Their Reaction with Arylhydroxymoyl Chlorides.

ChemInformVolume 43, Issue 20 Heterocyclic Compounds ChemInform Abstract: Heterocyclizations of Functionalized Heterocumulenes with C,N-, C,O-, and C,S-Binucleophiles. Part 13. Synthesis of Dialkyl 2-Oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates (III) and Their Reaction with Arylhydroxymoyl Chlorides. O. V. Kushnir, O. V. Kushnir Inst. Org. Chem., Natl. Acad. Sci. Ukr., Kiev 02094, UkraineSearch for more papers by this authorN. V. Mel'nichenko, N. V. Mel'nichenko Inst. Org. Chem., Natl. Acad. Sci. Ukr., Kiev 02094, UkraineSearch for more papers by this authorM. V. Vovk, M. V. Vovk Inst. Org. Chem., Natl. Acad. Sci. Ukr., Kiev 02094, UkraineSearch for more papers by this author O. V. Kushnir, O. V. Kushnir Inst. Org. Chem., Natl. Acad. Sci. Ukr., Kiev 02094, UkraineSearch for more papers by this authorN. V. Mel'nichenko, N. V. Mel'nichenko Inst. Org. Chem., Natl. Acad. Sci. Ukr., Kiev 02094, UkraineSearch for more papers by this authorM. V. Vovk, M. V. Vovk Inst. Org. Chem., Natl. Acad. Sci. Ukr., Kiev 02094, UkraineSearch for more papers by this author First published: 23 April 2012 https://doi.org/10.1002/chin.201220163Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume43, Issue20May 15, 2012 RelatedInformation

Synthesis of Dialkyl 2-(Dialkoxyphosphoryl)-3-(4-oxo-4,5-dihydro-thiazole-2-yl Sulfanyl) Succinates

A three-component reaction of trialkyl(aryl) phosphites, dialkyl acetylenedicarboxylates and rhodanine is described as a simple and efficient route for synthesis of dialkyl 2-(dialkoxyphosphoryl)-3-(4-oxo-4,5-dihydro-thiazole-2-yl sulfanyl) succinates in good yields. Protonation of the reactive 1:1 intermediate produced in the reaction between dialkyl acetylenedicarboxylate and triphenylphosphine by N′-formylbenzohydrazide leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of the NH acid to produce highly functionalized, salt-free phosphorus ylides in excellent yields.

Efficient Synthesis of Succinate Derivatives using Mercaptoalkanols or Mercaptophenols

A one-pot synthesis of dialkyl 2-(diphenoxyphosphoryl)-3-[hydroxy (alkyl)(aryl) sulfanyl] succinate derivatives via the reaction between dialkyl acetylenedicarboxylates, triphenyl phosphite and mercaptoalkanols or mercaptophenols is described. These reactions lead to the formation of dialkyl 2-(diphenoxyphosphoryl)-3-[hydroxy (alkyl)(aryl) sulfanyl] succinates as a mixture of two diastereomers without using any catalyst and in good yields.

Heterocyclizations of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: XIII. Synthesis of dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates and their reaction with arylhydroxymoyl chlorides

Dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates obtained by condensation of 1-chlorobenzyl isocyanates with N-allylfumarates reacted regioselectively with arylhydroxymoyl chlorides with the formation of dialkyl 6-aryl-3-[(3-aryl-4,5-dihydro-5-isoxazolyl)methyl]-2-oxo-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates.

One-pot, three component reactions between isocyanides and dialkyl acetylenedicarboxylates in the presence of phenyl isocyanate: synthesis of dialkyl 2-(alkyl/arylimino)-2,5-dihydro-5-oxo-1-phenyl-1H-pyrrole-3,4-dicarboxylate

The reactive 1:1 adduct, generated from the reaction between alkyl/aryl iscyanides and dialkyl acetylenedicarboxylates, was trapped by phenyl isocyanate to yield dialkyl 2-(alkyl/arylimino)- 2,5-dihydro-5-oxo-1-phenyl-1H-pyrrole-3,4-dicarboxylate in good yields.

Synthesis of Dialkyl 2-(4-oxopyridin-1(4H)-yl)dicarboxylates Through the Reaction of 4-hydroxypyridine and Dialkyl Acetylenedicarboxylate in the Presence of Triphenylphosphine

Hydroxypyridine undergoes a smooth reaction with dial- kyl acetylenedicarboxylates in the presence of triphenylphosphine (15 mol %) to produce the E/Z isomers of dialkyl 2-(4-oxopyridin-1(4H)- yl)but-2-enedioates in high yields.