Michael A. Pudovik

New Calix[4]Resorcinols with Thiophosphoryl-Containing Fragments

Abstract The condensation of thiophosphorylated aldehydes 1 and 2 with resorcinol and its derivatives leads to the formation of the new type of calix[4]resorcinols with four thiophosphoryl groups inserted to the substituents located in methylidene bridges of the molecule. The conformation of these compounds was found to be “flattened partial cone” or “chair,” which was determined by NMR methods and a single-crystal X-ray diffraction study. GRAPHICAL ABSTRACT

Single step preparation and conformational analysis of novel thiophosphorylated ligands based on calix[4]resorcinol matrix

We have synthesized novel calix[4]resorcinols with four 2-thioxo-1,3,2-dioxaphospholane groups introduced in aromatic substituents in the methylidene bridges of macromolecules by the condensation of new thiophosphorylated benzaldehyde with resorcinol and its derivatives in acidic media with high yields. The formation of only one rctt isomer with corresponding chair conformation is observed, which was determined by 2D NMR-experiments.

SYNTHESIS OF NEW PHOSPHORUSCONTAINING THREE-DIMENSIONAL STRUCTURES ON THE BASIS OF CALIX[4] RESORCINARENES

Abstract Phosphorylation of calix[4]resorcinarenes with long chain aliphatic radicals (R=C6, C,. C,) (1a,b,c) with a number of P(III) derivatives i.e. triamido- and diamidophosphites, triphenylphosphite, monoand polyhalogenides of P(III) is described. A series of phosphoamide cavitands (2), (3) were obtained. A new three-dimensional “container”- like structures, in which tetraresorcinol fragments are connected by means of phosphite bridges (13,14) were formed in the reaction of (Ib) with (-) bis(N,N-diethylamido)menthylphosphite, phosphorus trichloride and triphenylphosphite. Phosphorylation of calix[4]resorcinarene (1c) with chloroanhydrides of chloromethylphosphonic and bis(chloromethyl) phosphinic acids results in completely or partially posphorylated products depending on the reaction conditions. The synthesis of dimeric “head to head” macrocyclic derivative of chlormethylphosphonic acid (19) is described. Structures and properties of synthesized compounds were discussed on the basis of physical and q...

Synthesis and Properties of Novel Calix[4]Resorcinols Containing Phosphonium Substituents

Abstract Condensation of resorcinol and its derivatives with novel phosphonium-substituted acetals under conditions of acidic catalysis yields either calix[4]resorcinols containing four phosphonium fragments or phosphonium salts including diarylmethane moiety depending on the structure of the phosphorus-containing reagent. The latter, in turn, undergo condensation with propionic aldehyde forming new calix[4]resorcinols with alternating phosphonium and ethyl substituents, which have remarkable surface-active properties. GRAPHICAL ABSTRACT

New P-Containing Linear and Macrocyclic Polyphenols

Abstract We synthesized new phosphorus-containing linear and macrocyclic polyphenols using organic compounds containing phosphorus-carbon bonds and the phosphorus atom of various coordination, and also with reactive acetal, aldehyde, vinylethoxy, and methylene quinone fragments as starting materials. These achievements are briefly summarized.

Nitrogen-containing acetals and ketals in the synthesis of pyrrolidine derivatives

n This review offers analysis and generalization of data regarding the synthesis of substituted pyrrolidines by using nitrogen-containing acetals and ketals as starting compounds published from year 2000 to 2016. Particular attention has been focused on the synthesis of pyrrolidines that are substituted at position 2. Biological activity data for several pyrrolidine derivatives are reported.

Phosphorylated and Silylated Derivatives of Alfa-Mercaptocarbonyl Compounds

Abstract The phosphorylation and silylation of α-mercaptocarbonyl compounds have been investigated. Novel different cyclic and linear silicon(phosphorus) containing derivatives have been obtained.

Acid-catalyzed reaction of phenols with N-(4,4-diethoxybutyl)sulfonamides – a new method for the synthesis of 2-aryl-1-sulfonylpyrrolidines

nWe have developed a new method for the synthesis of 2-aryl-1-sulfonylpyrrolidines on the basis of reactions between various phenols and N-(4,4-diethoxybutyl)sulfonamides in the presence of trifluoroacetic acid. The structures of the obtained products were confirmed by 1H and 13C NMR spectroscopy, IR spectroscopy, and X-ray structural analysis.

The Syntheses and Binding Properties of the Novel Organophosphorus Calixarenes

Phosphorylation of bromo, dialkylaminomethyl calix[4]resorcinarenes with various long chain aliphatic radicals with a number of P(III) derivatives i.e. triamido-and diamidophosphites, and polyhalogenides of P(III), P(IV) is described. A series of phosphoamide cavitands were obtained. Structures and properties of synthesized compounds were discussed on the basis of physical and quantum chemical methods.

Phosphorus-containing calix[4]resorcinols: Synthesis and properties

GRAPHICAL ABSTRACT Abstract The presented mini-review summarizes the results of our study of the condensation of resorcinol and its derivatives with phosphorylated acetals, aldehydes, and vinylphosphonates with an aim to prepare new calix[4]resorcinols (thio)phosphorylated on the lower rim of macromolecule. The properties of the synthesized macrocyclic compounds are studied and some aspects of their possible application are considered.