Synthesis of novel “hybrid” structures based on phosphorylacetic acid hydrazides and sterically hindered phenols

N-Benzylation of acylhydrazones of the hydroxybenzaldehyde series with 3,5-di-tert-butyl-4-hydroxybenzyl acetate was performed at room temperature in the absence of acid or base catalysts. Carboxamides do not react with 3,5-di-tert-butyl-4-hydroxybenzyl acetate under similar conditions. N-Benzylation of isoniazid and (diphenylphosphoryl)acetic acid hydrazones was shown to be an effi cient method for the synthesis of new hybrid compounds containing moieties of biologically active acylhydrazones and sterically hindered phenols. N-Benzyl derivatives of isoniazid and (diphenylphosphoryl)acetic acid hydrazones containing a hydroxy group at the ortho position of the aromatic ring are formed as individual E isomers with respect to the C=N double bond.

show abstract

“…Acylhydrazones 2a,b, 25 2c, 26 6, 27 4c, 28 and 9 (see Ref. 28) were synthesized by procedures described previously.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

Modular Synthesis of Phosphino Hydrazones and Their Use as Ligands in a Palladium‐Catalysed Cu‐Free Sonogashira Cross‐Coupling Reaction

et al. 2023

View full text Add to dashboard Cite

Phosphino hydrazones represent a versatile class of nitrogen‐containing phosphine ligands. Herein, we report a modular synthesis of phosphino hydrazone ligands by hydrazone condensation reaction of three different aryl hydrazines with 3‐(diphenylphosphino)propanal (PCHO). Complexation reactions of these phosphino hydrazone ligands with palladium(II) and platinum(II) were investigated and the catalytic activity of the palladium(II) complexes was explored in a Cu‐free Sonogashira cross‐coupling reaction achieving yields up to 96 %. Additionally it was shown that the catalytically active species is homogeneous.

show abstract

Reactions of derivatives of phosphorylacetic acid hydrazides with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

Бухаров

Khabibullina

Akylbekov

et al. 2019

Synthetic Communications

View full text Add to dashboard Cite

Melting points were determined on a melting point apparatus and are uncorrected. The 1 H NMR spectra were recorded on Bruker AVANCE 400 (Bruker BioSpin, Rheinstetten, Germany) NMR spectrometer (400.13 MHz) using tetramethylsilane as an internal standard and the chemical shifts are reported in δ units. The IR spectra were recorded on a TENSOR 27 Fourier spectrometer (Bruker Optik GmbH, Karlsruhe, Germany) in the range 400-4000 сm -1 . Crystalline samples were studied as emulsions in vaseline oil. Elemental analyses were performed on a CHNS-O Elemental Analyser EuroEA3028-HT-OM (EuroVector S.p.A., Milan, Italy) with an accuracy ±0.4% for C, H and N. Most chemicals were purchased from commercial sources. Solvents were of analytical grade and were used without further purification unless otherwise stated. MALDI-TOF experiments were performed with an Ultraflex III TOF/TOF (Bruker Daltonics, Germany) mass spectrometer equipped with a Nd:YAG laser. The spectra were measured in the positive ion linear modе. MS data were processed using the software FlexAnalysis 3.0 from Bruker Daltonics.2-(Diphenylphosphoryl)-2- (3',5'-di-tert-butyl-4'-hydroxybenzyl)methyl acetate (5, С 30 H 37 O 4 Р) A solution of 1.0 g benzyl acetate 3 (3.6 mmol), 0.9 g ether 4 (3.3 mmol) and 2 cm 3 of triethylamine in 30 cm 3 of DMF was kept at 25 °C for 5 days. The reaction mixture was poured into saturated NaCl solution. The precipitate was filtered off, washed with water and dried in air to constant weight. The dry precipitate was washed with hot hexane 3 times. Yield 0.4 g (45%), the product is white powder.

show abstract

Synthesis of novel “hybrid” structures based on phosphorylacetic acid hydrazides and sterically hindered phenols

Cited by 4 publications

References 30 publications

Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

Modular Synthesis of Phosphino Hydrazones and Their Use as Ligands in a Palladium‐Catalysed Cu‐Free Sonogashira Cross‐Coupling Reaction

Reactions of derivatives of phosphorylacetic acid hydrazides with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

Contact Info

Product

Resources

About