Natalya M. Vinogradova

Extraction Properties of P(O)-Modified N-Aryl-Carbamoylmethylphosphine Oxides in Nitric Acid Media

Novel polyfunctional neutral organophosphorus compounds, P(O)-modified N-aryl- carbamoylmethylphosphine oxides, Ph2P(O)CH2C(O)NH-(o-C6H4)(CH2)n-P(O)Ph2 and Ph2P(O)CH2C(O)NH-(m-C6H4)(CH2)n-P(O)Ph2 (n = 1,2), were synthesized and studied as extractants for U(VI), Th(IV) and Ln(III) from HNO3 solutions. The influence of aqueous and organic phases on the extraction efficiency was elucidated and stoichiometry of the complexes extracted was determined. Introduction of an additional phosphoryl group into the phenyl substitutent at the nitrogen atom of diphenyl(N-phenylcarbamoylmethyl)phosphine oxide resulted in an increase of the efficiency of U(VI), Th(IV), Ln(III), and Re(VII) extraction.

The Selective C-Mono-and C,C-Dialkylation of Thiophosphorylacetonitriles and Reactivity of the Products

The facile synthetic route to selective C-mono-and C,C-dialkylation of thiophosphorylacetonitriles by primary haloalkanes under phase transfer catalysis conditions has been developed. Using under the same conditions unsymmetric α,ω-dihaloalkanes results in different linear and cyclic products depending on the alkylene chain length. 3-Halopropylsubstituted thiophosphorylacetonitriles synthesized transform to mono-and bis-heterophosphacyclanes under elevated temperatures.

SYNTHESIS AND X-RAY STRUCTURE OF 6-CYANO-2,10-DIOXA-1-PHOSPHABICYCLO [4.4.0]DECANE-1-OXIDE

Abstract Bis(ω-chloropropyl)dialkoxyphosphonylacetonitriles 4 were established to undergo intramolecular bisdealkylation during distillation affording 6-cyano-2,10-dioxa-1-phosphabicyclo[4.4.0]decane-1-oxide 5 in high yield. The molecular structure of 5 was determined by the single crystal X-ray diffraction method. The molecule consists of cis-fused six-membered rings both in chair conformation.

Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity

A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.

Novel 3-Cyanosubstituted 1,2-Thiaphosphacyclanes: Synthesis and Stereochemistry

The facile synthetic route to 5- and 6-membered 3-cyano-2-oxo-1,2-thiaphosphacyclanes and 6-cyano-2-oxa-10-oxa(thia)-phosphabicyclo [4.4.0]-decane-1-oxides was elaborated via intramolecular S-alkylation in a series of y -haloalkylsubstituted thiophosphorylacetonitriles. The compounds were used to prepare novel P(III)-containing bidentate ligands with definite stereochemistry. Diastereomeric transformations among 2-oxo-1,2-thiaphosphinanes were found and the mechanism of such transformations is suggested.

Bis(carbamoylmethylphosphine oxide) ligands fixed on the arene core via 1,2,3-triazole linkers: Novel effective extractants for palladium, lanthanides and actinides

GRAPHICAL ABSTRACT ABSTRACT Novel polydentate neutral organophosphorus ligands containing two diphenyl-(diethylcarbamoyl-methyl)phosphine oxide moieties fixed on the arene platform via methylene-1,2,3-triazole linkers (Ar-CMPO) were synthesized by the method of click chemistry and studied as an extractant for Pd(II), U(VI), Th(IV), and lanthanides(III) ions from HNO3 solutions.

Phosphorylation of natural products—Cytisine, anabasine, and camphor using click chemistry methodology

GRAPHICAL ABSTRACT ABSTRACT Anabasine-, cytisine-, and camphor-containing azides and acetylenes were used as building blocks in copper(I) catalyzed 1,3-dipolar cycloaddition reactions with a series of acetylenes and azides via click chemistry to provide a range of anabasine, cytisine, and camphor conjugates that are substances with potential biological activity.

New 3-Cyano-1,2λ 3 -Thiaphosphacyclanes and Their Complexing Properties

Reduction of both individual diastereomers of 2-oxo-1,2-thiaphosphacyclanes by HSiCl 3 proceeds with retention of cyclic structure, cyano-group, and stereochemical configuration.

SelectiveC-mono- andC,C-dialkylation of thiophosphorylacetonitriles

Alkylation of thiophosphorylacetonitriles under phase transfer catalysis conditions in the 50% NaOH/CH2Cl2 system proceeds as monoalkylation, whereas alkylation in MeCN with the use of solid KOH as a base gives a disubstituted product. The order in which the reagents were added as well as dilution of the reaction mixture affected substantially the yields of the target compounds. X-ray diffraction analysis of a single crystal of dibutyl(diphenylthiophosphoryl)acetonitrile was carried out.