Convenient syntheses of functionalized phosphorus-containing carboxamides based on the reaction of adducts of imines and carboxylic acid chlorides with trimethylsilyl esters of trivalent phosphorus acids have been developed. Adducts ClCH(Ar)—N(R)C(O)R′ are convenient synthons for the preparation of the target phosphorus-containing carboxamides bearing P(O)—C—N—C(O) moieties. The resulting compounds contain polar amide and phosphoryl moieties, have potential biological activity, and are also of interest as effective extractants and polydentate chelating ligands.

Convenient synthesis of functionalized phosphorus-substituted dialkylamides of organophosphorus acids based on 1,3,5-trisubstituted hexahydro-1,3,5-triazines has been developed, and key aminomethylphosphonates containing NSi and NH moieties have been obtained. These compounds are convenient synthons for the synthesis of the target phosphorus-substituted amides of phosphorus acids containing P—C—N—P and P—C—N—C—C—N—P units. The resulting substances bear bioactive aminomethyl and thiophosphoryl moieties, have potential biological activity, and are also of interest as effective extractants and polydentate chelating ligands.

Convenient syntheses of functionalized bisorganophosphorus acids and their derivatives containing hydroxymethylene moieties have been developed. Trimethylsilyl esters of trivalent phosphorus acids react with acyl chlorides to give new hydroxymethylene-substituted functionalized bisorganophosphorus acids containing P—C—P units. The resulting compounds are structural analogs of pharmaceutical agents used to treat various diseases. They are also of interest as promising biologically active substances and effective polydentate ligands.

Convenient syntheses of functionalized PCHNH-containing amines have been developed based on the nucleophilic addition of trivalent phosphorus acid esters to various imines. Subsequent acylation of these amines at the NH fragment opens the way to promising types of amides and sulfonamides of functionalized aminomethyl-substituted organophosphorus acids. The resulting compounds contain polar amide (sulfonylamide) and phosphoryl moieties, have potential biological activity, and are also of interest as effective extractants and polydentate chelating ligands.

Convenient syntheses of phosphorus-substituted amines containing P(O)CH2NH and P(O)CH2NSi moieties based on the reaction between N,N′,N″-trisubstituted hexahydro-1,3,5-triazines and trivalent phosphorus acid esters have been developed. Various functionalization reactions (2-carboxyethylation, 2-pyridylethylation, and acylation) of the NH and NSi units of the resulting synthons proceed under mild conditions and give new functionalized phosphorus-containing amines in high yields. The resulting compounds are of interest as promising biologically active substances, water-soluble polydentate ligands, and effective extractants.

Convenient syntheses of functionalized PCH2N-containing mono-, bis-, and tris-(spirophosphoranylmethyl)amines and analogous amino acids based on hydrospirophosphoranes of the 1,4,6,9-tetraoxa-5λ5-phosphaspiro[4.4]nonane type using mono-, bis-, and tris-aminomethylating agents have been developed. Transesterification of diethyl esters of N,N-disubstituted aminomethylphosphonous acids with ethylene glycol is accompanied by a redox process and furnishes aminomethylspirophosphoranes. The target compounds are of interest as biologically active substances, polydentate chelating ligands, and also as promising monomers for the synthesis of phosphorus-containing polymers.

Convenient synthesis of functionalized bis(2,2,2-trifluoroethyl) phosphonates based on tris(2,2,2-trifluoroethyl) phosphite using N-chloromethylamino carboxylic acids and carbonyl compounds has been developed. The resulting compounds containing functionalized N-amidomethyl and phosphoryl moieties have potential biological activity, and are of interest as effective extractants and polydentate chelating ligands, as well as components of lithium-ion battery electrolytes.

Convenient syntheses of functionalized hydroxymethyl-substituted organophosphorus acids and their derivatives have been developed. Trimethylsilyl esters of trivalent phosphorus acids react with various aldehydes and ketones to give new hydroxymethyl-substituted phosphonous, phosphonic and phosphinic acids with P—C—O units. The resulting compounds are of interest as promising biologically active substances, water-soluble polydentate ligands, and effective extractants.

Convenient syntheses of mono- and diphosphorus-containing amino acid derivatives based on 1,3,5-[ω-(alkoxycarbonyl)alkyl]hexahydro-1,3,5-triazines have been developed. The reaction of PH acids with readily available hexahydro-1,3,5-triazines and N-substituted bis(alkoxymethyl)amines obtained therefrom gives new mono- and diphosphorus-substituted amino acids containing P(O)CH2NH and P(O)CH2NCH2P(O) units together with glycine, β-alanine and γ-aminobutyric acid residues. The resulting compounds are of interest as promising biologically active substances, effective extractants, and water-soluble polydentate ligands.

Convenient syntheses of organophosphorus analogs of α- and β-alanine containing functionalized phosphonous and phosphinic acid moieties based on readily available trimethylsilyl esters of trivalent phosphorus acids have been developed. Nucleophilic addition of bis(trimethylsiloxy)phosphine to trimethylsilyl acrylates or α-(acetylamino)-acrylates proceeds regioselectively to give [2-(trimethylsiloxycarbonyl)ethyl]phosphonites, the subsequent functionalization of which affords various derivatives of the target acids. The resulting compounds are of interest as promising biologically active substances and water-soluble ligands.

Convenient syntheses of functionalized 2-hydroxyalkyl-substituted organophosphorus acids and their derivatives based on nucleophilic addition of trimethylsilyl esters of tricoordinated phosphorus acids to functionalized oxiranes have been developed. 2-Trimethylsiloxyalkyl-substituted phosphonites are effective synthons for the production of new functionalized 2-hydroxyalkyl-substituted organophosphorus acids bearing amino, carboxy or sulfo groups. The resulting compounds are of interest as potential bioactive substances, promising extractants and polydentate ligands.

A convenient synthesis of functionalized N-acylated amino acids containing 3- and 4-coordinated phosphorus moieties as well as N-alkoxycarbonyl groups has been developed. Aminomethylation of tricoordinated phosphorus acid esters with N-chloromethylsubstituted N-alkoxycarbonylamino acids proceeds under mild conditions and affords new types of target products of different structures. The resulting compounds are of interest as promising biologically active substances, effective extractants, and water-soluble polydentate ligands.

Convenient syntheses of functionalized phosphonous and phosphinic acids containing hydrolysis-resistant triethylgermyl moieties have been developed. Radical addition of bis(trimethylsiloxy)phosphine to (triethyl)(vinyl)germane occurs regioselectively to give novel germanium-containing ethylphosphonites, the subsequent functionalization of which affords various target acids. The resulting compounds are of interest as promising biologically active substances and water-soluble ligands.

A convenient synthesis of pyrrolidones substituted with functionalized phosphonous, phosphonic, and phosphinic acid residues has been developed. The radical addition of bis(trimethylsiloxy)phosphine to N-vinylpyrrolidone proceeds regioselectively to give 2-pyrrolidone-substituted ethylphosphonite, and its subsequent functionalization affords the target products. The resulting compounds are of interest as promising biologically active substances and water-soluble ligands.

Convenient methods for the synthesis of a series of organophosphorus analogs of glycine containing aminomethyl groups as well as azaheterocyclic and amino acid moieties have been developed. Aminomethylation of phosphinic acid esters with chloro-, alkoxy- and amino-substituted methyl(dialkyl)amines affords various new functionalized aminomethylphosphonites and bis(aminomethyl)phosphinates. The resulting compounds are of interest as promising biologically active substances, extractants, and water-soluble ligands.

A convenient synthesis of functionalized phosphorus-substituted derivatives of γ-butyrolactone based on readily available γ-crotonolactone and trimethylsilyl esters of trivalent phosphorus acids has been developed. The addition of bis(trimethylsiloxy)phosphine to γ-crotonolactone proceeds regioselectively to give phosphonites containing γ-butyrolactone moieties, the subsequent functionalization of which leads to a variety of target derivatives. The resulting compounds are of interest as promising biologically active substances and water-soluble ligands.

Convenient synthesis of phosphorus-containing derivatives of succinic acid, which contain functionalized phosphonous, phosphonic, and phosphinic acid moieties have been developed. The nucleophilic addition of bis(trimethylsiloxy)phosphine to diesters of maleic, itaconic, and acetylenedicarboxylic acids proceeds regioselectively to give a number of functionalized phosphonites. Further aminomethylation of these compounds affords various target acid derivatives. The resulting compounds are of interest as promising biologically active substances and water-soluble ligands.

A series of new N-substituted derivatives of octahydrothieno[3,4-b]pyrazine 6,6-dioxide were synthesized for further biological screening.

A convenient synthesis of organophosphorus analogs of β-phenylalanine containing functionalized 2-phenylethylphosphonous and 2-phenylethylphosphinic acid moieties has been developed. The radical addition of bis(trimethylsiloxy)phosphine to styrene, trimethylsilyl cinnamate, or arylacetylenes proceeds regioselectively to give a variety of substituted 2-phenylethylphosphonites, and the subsequent functionalization affords various derivatives of the target acids. The resulting compounds are of interest as promising biologically active compounds and water-soluble ligands.

A convenient synthesis of functionalized 2-diphenylphosphinoethyl-containing phosphonous and phosphinic acids has been developed. Radical addition of bis(trimethylsiloxy)-phosphine to diphenyl(vinyl)phosphine and phenyl(divinyl)phosphine proceeds regioselectively to give new 2-phosphino-substituted ethylphosphonites, the subsequent functionalization of which affords the target phosphinic acids and a variety of their derivatives. The resulting compounds are of interest as effective water-soluble ligands and promising biologically active substances.