79202-15-6

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 552-89-6 2-nitro-benzaldehyde 
• 122-52-1 triethyl phosphite 

Downstream Products

• 1181811-99-3 diethyl α-chloro-2-nitrobenzylphosphonate 
• 1181811-93-7 diethyl α,α-chlorofluoro-2-nitrobenzylphosphonate 
• 1326345-19-0 diethyl α,α-bromofluoro-2-nitrobenzylphosphonate 
• 375372-35-3 (R)-4-[(E)-2-(2-Isocyano-phenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 375372-37-5 3-pentyl-2-phenylsulfanyl-1H-indole 
• 1027208-32-7 3-cyclohexyl-2-ethylsulfanyl-1H-indole 
• 375372-32-0 Diethyl [(2-isocyanophenyl)methyl]phosphonate 
• 375372-41-1 1-(cyclohexylidenemethyl)-2-isocyanobenzene 
• 375372-34-2 (S)-4-[(E)-2-(2-Isocyano-phenyl)-vinyl]-2,2-dimethyl-[1,3]dioxolane 
• 156049-40-0 (E)-1-isocyano-2-styrylbenzene 
• 375372-33-1 1-((E)-3,3-Dimethyl-but-1-enyl)-2-isocyano-benzene 
• 156049-42-2 C₁₃H₁₅N 
• 100717-32-6 3-cyclohexyl-1H-indole 
• 16886-10-5 3-benzyl-1H-indole 

Relevant academic research and scientific papers

O-allylated pudovik and passerini adducts as versatile scaffolds for product diversification

The palladium-catalyzed O-allylation of α-hydroxyphosphonates and α-hydroxyamides obtained from Pudovik and Passerini multicomponent reactions has allowed interesting and highly straightforward access to a variety of building blocks for product diversific

Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes

We synthesized substituted benzaldehyde derived α-hydroxyphosphonates (αOHP), α-hydroxyphosphonic acids (αOHPA) and α-phosphinoyloxyphosphonates (αOPP) and characterized their cytotoxicity against a panel of cancer cell lines. A library containing 56 analogues was screened against Mes-Sa parental and Mes-Sa/Dx5 multidrug resistant uterine sarcoma cell lines, using a fluorescence-based cytotoxicity assay. The cytotoxicity screening revealed that dibenzyl-αOHPs and dimethyl-α-diphenyl-OPPs were the most active clusters, which encouraged us to synthesize further dibenzyl-α-diphenyl-OPP derivatives that elicited pronounced cell killing. Further structure-activity relationships showed the relevance of hydrophobicity and the position of substituents on the main benzene ring as determinants of toxicity. The most active analogs proved to be equally, or even more toxic to the multidrug resistant (MDR) cell line Mes-Sa/Dx5, suggesting these compounds may overcome P-glycoprotein mediated multidrug resistance by evading the drug transporter.

Biocatalytic Promiscuity of Lipases in Carbon-Phosphorus Bond Formation

A promiscuous lipase-catalyzed carbon-phosphorus bond formation is presented. The developed enzymatic Pudovik-Abramov reaction of various aromatic and aliphatic aldehydes with dialkyl phosphonates provides biologically and pharmacologically relevant α-hyd

Rational synthesis of α-hydroxyphosphonic derivatives including dronic acids

New, green methods have been elaborated for the syntheses of α-hydroxyphosphonates and α-hydroxymethylenebisphosphonic derivatives (HMBPs, dronates). α-Hydroxyphosphonates were prepared via the Pudovik reaction, while the synthesis of HMBPs has been performed in the three-component reaction of carboxylic acids, phosphorus trichloride and phosphorus acid.

Palladium-catalysed O-Allylation of α-Hydroxyphosphonates: An Expedient Entry into Phosphono-oxaheterocycles

We report here an unprecedented palladium-catalysed O-allylation of α-hydroxyphosphonates. The method was eventually included in a sequential Pudovik/Tsuji-Trost type O-allylation/Ring-Closing Metathesis to afford a variety of phosphorylated heterocycles

Hydrophosphonylation of aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes

This work reports the first method for the synthesis of α-hydroxyphosphonates from aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes. The best results were obtained using the system HP(O)(OEt)2/[RuClCp(PPh3)2

Highly efficient green synthesis of α-hydroxyphosphonates using a recyclable choline hydroxide catalyst

Choline hydroxide has been found to be an efficient basic ionic liquid catalyst for the synthesis of α-hydroxyphosphonates. Hydrophosphonylation of aldehydes was performed via the nucleophilic addition of diethylphosphite to aldehydic carbonyl compounds, in the presence of choline hydroxide under neat as well as solvent conditions. A wide array of substrates, including aromatic, fused aromatic, and heterocyclic aldehydes, were efficiently converted to their corresponding products in good yields. This protocol provides an alternative method for the straightforward synthesis of α-hydroxyphosphonates in high yields.

MgO-coated-Fe3O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of 1-hydroxyphosphonates

Nanosize magnetic particles coated with magnesium oxide (core/shell nanoparticles) have been prepared and used for the synthesis of 1-hydroxyalkyl phosphonates. Catalytic activity studies show that the magnetic particles coated with magnesium oxide have h

Applications of caged-designed proton sponges in base-catalyzed transformations Dedicated to Professor Milan Kratochvíl for his 90th birthday anniversary.

Superbasic properties of caged proton sponges (PSs) - substituted diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) - were utilized in Knoevenagel and Claisen-Schmidt condensations, the Pudovik reaction, and Michael addition. This investigation covers the influence of the solvent, reaction temperature, catalyst loadings as well as the electronic properties of substituents upon the reaction. Moreover, we provided an activity comparison between our new base and a well-known and commercially available proton sponge (DMAN). The basicity (in MeCN) of our chosen DTD (pKBH+=21.7±0.1) exceeded the prototypal PS - 1,8-bis(dimethylamino)naphthalene (DMAN, pKBH+=18.6), by three orders of magnitude. We proved that DTDs are reasonably active species in monitored reactions, which is a consequence of a hydrogen bridge angle (～130°) between the two nitrogen atoms and the captured proton. We present here syntheses of aminoindolizine, substituted 4H-chromene, and flavanones, and the unexpected formation of a bis-addition product formed after Michael addition, all under mild conditions.

Synthesis, structure, and catalytic activity of novel trinuclear rare-earth metal amido complexes incorporating μ-η5:η1 bonding indolyl and μ3-oxo groups

The reactions of different pyrrolyl-functionalized indoles with rare-earth metal(iii) amides [(Me3Si)2N]3RE III(μ-Cl)Li(THF)3 (RE = Yb, Er, Dy, Eu, Y) produced different kinds of rare-earth metal amid