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The reactions of organosilicon derivatives of octacis(2-hydroxyethylated) calix[4]resorcinarenes with phosphoryl trichloride and subsequent hydrolysis of the resulting phosphorochloridates has afforded novel water-soluble calix[4]resorcinarenes containing eight phosphorus acid fragments at the outer rim of the molecule. The synthesized phosphorodichloridate derivatives on a calixarene platform are convenient precursors for the synthesis of the corresponding phosphoramidates.

The reactions of pyridoxal imidazolidines with diphenylchlorophosphine oxide, depending on the substituents nature in the imidazolidine ring, resulted in the formation of new salt-like tricyclic structures or a bisalt structure based on N,N′-dibenzylethylenediamine and diphenylphosphinic acid. The benzoylation of pyridoxal imidazolidines also led to decomposition of the imidazolidine fragment with the formation of dibenzoylated N,N′-dimethylethylenediamine.

The reaction of phenyl isocyanate with pyridoxal is carried out with the participation of hydroxymethyl and phenolic groups with the formation of dicarbamate derivatives. The reactions of pyridoxal azomethines with phenyl isocyanate, depending on the structure and the ratio of the starting reagents, lead to the formation of mono-, di- or tricarbamate derivatives. The product of addition of azomethine pyridoxal to phenyl isocyanate with the participation of a hydroxymethyl group was obtained.

The reaction of equimolar amounts of pyridoxal and 1,2-propylenediamine leads to the formation of monoimine, which exists as a cyclic imidazolidine tautomer. The latter reacts with aromatic aldehydes to form unsymmetric bisazomethines. The reaction of azomethine with phenylisocyanate produces a compound containing a carbamate group, and the reaction with hydrochloric acid leads to the formation of a salt-based furopyridine.

The review systematizes and summarizes data on the synthesis of structurally diverse cyclic ureas published over the last 10 years. Saturated and unsaturated monocyclic ureas, as well as fused heterocycles containing one urea moiety, are considered. Data on the biological activity of selected compounds of this type are provided. The synthetic approaches to cyclic carbamides are classified in terms of the reaction type and the source of a carbonyl group. The bibliography includes 235 references.

A rapid diastereoselective construction of the polycyclic quinoline scaffold has been developed through the triflic-acid catalysed tandem intramolecular cyclization/Povarov reaction of (2,2-dialkoxyethyl)ureas.

The first representatives of diarylmethanes and dibenzoxanthenes bearing aminoalkylphosphoryl moieties were synthesized via the reaction of phosphorylated acetals with phenols. Structures of the resulting compounds were confirmed using a set of physico-chemical methods of analysis.

It was found that the reaction of 2-hydroxy-5,7,8-trimethyl-2H-1,2-benzoxaphosphinine 2-oxide with resorcinol and its derivatives as well as sesamol leads to the formation of phosphaneoflavanones in high yields. The obtained phosphaneoflavanones are precursors in the synthesis of novel unsymmetrical cage phosphonates. The structures of the obtained products were confirmed by IR spectroscopy, 1H, 13C NMR spectroscopy, and X-ray structural analysis.

The reactions of pyridoxal monoimine based on ortho-phenylenediamine with aliphatic aldehydes results in the formation of new C-alkyl-N-pyridoxylmethylbenzimidazoles.

An efficient procedure has been developed for the synthesis of analogs of the alkaloid norhygrine by reaction of 3-(arylmethylidene)-1-pyrrolines with acetone. The synthesized compounds have been converted to hydrazones by treatment with the corresponding substituted arylhydrazines.

A series of new α-aminophosphonates was synthesized based on the acid-catalyzed Kabachnik–Fields reaction involving diethyl phosphite, cyclohexylamine and substituted benzaldehyde. Structure of the reaction products was established by IR, NMR spectroscopy, and mass spectrometry methods.

Pyridoxal monoimines were obtained by the reaction of pyridoxal with aromatic diamines. A change in the ratio of the reagents or introduction of another aromatic aldehyde into the reaction leads to the formation of symmetric and asymmetric diimines. In some cases, the initially formed diimines are transformed into the corresponding benzimidazoles. The products of the reaction of pyridoxal with 1,3-diaminobenzene have a furopyridine structure.

Based on the acid-catalyzed reaction of functionalized aminoacetals with

Pyridoxal in the absence of catalyst forms furo[3,4-c]pyridine species (ortho aldehyde and hydroxymethyl groups are involved) which is further transformed into C–C hybrid with 4-hydroxycoumarin. Different products of chromeno-[3′,4′:5,6]pyrano[2,3-c]pyridine type are formed when pyridoxal hydrochloride or more sophisticated 2,4-dihydroxybenzaldehyde derivative are applied (herein, ortho aldehyde and hydroxy groups are involved into heterocyclization).

The reactions of N-(4,4-diethoxybutyl)amidophosphates with С-nucleophiles in chloroform in the presence of trifluoroacetic acid provided new 2-hetarylpyrrolidines. The reaction proceeded under mild conditions and gave good yields in the absence of metal-based catalysts.

The reaction of N-(4,4-diethoxybutyl)phosphamides with chloro(diphenyl)phosphine in chloroform in the presence of acetic acid gave previously unknown 2-(diphenylphosphoryl)pyrrolidines, and hydrolysis of the latter afforded 2-(diphenylphosphoryl)pyrrolidine.

Pyrrolinium salts containing 3-arylidene fragment were obtained. Their synthesis is based on the reaction of (E)-4-(4-chlorobenzylidene)-3,4-dihydro-2H-pyrrole with various bromo-alkanes. Structures of the obtained compounds were confirmed by a set of physico-chemical analysis methods.

Published data on ring opening reactions of nitrogen-containing cyclic compounds resulting in various acyclic products are integrated and systematized. The reactions of common five-, six- and seven-membered nitrogen heterocycles containing one to four nitrogen atoms in the ring and having various structures (mononuclear, polynuclear, fused, saturated, unsaturated and aromatic) are considered. Special emphasis is made on the potential of nitrogen heterocycles for the synthesis of polyfunctional open-chain compounds. The advantages and disadvantages of the proposed approaches are noted. Data on the biological activities of some ring opening products of the title heterocycles are presented. The text is arranged according to the type of reagents and catalysts used. The bibliography includes 196 references.

The reactions of 4-methylpiperazin-1-amine, 2-amino- and 4-aminomethylpiperidines with pyridoxal afforded the corresponding azomethines. Their reactions with organic and inorganic acids lead to the formation of salt derivatives of pyridoxal azomethines.

Regioisomeric cage phosphonates have been prepared and isolated for the first time by the reaction of 4-methyl- and 4,6-dimethylresorcinols with (2-ethoxyvinyl)phosphonic dichloride. It has been shown that different phosphorus-containing heterocyclic compounds are formed depending on the nature of substituent at positions 4 and 6 of resorcinol aromatic ring.

The reactions of 1-(4,4-diethoxybutyl)ureas with diphenyl chlorophosphine in the presence of acetic acid afforded new 2-(diphenylphosphoryl)pyrrolidine-1-carboxamides.

The acid-catalyzed reaction of {2-[1-(2,2-dimethoxyethyl)-3-(phenylcarboxamido)]ethyl}phosphonate or diethyl [2-(2-oxo-3-phenyl-2,3-dihydro-1H-imidazol-1-yl)ethyl]phosphonate with resorcinol and its derivatives afforded new 4(5)-arylimidazolin-2-ones. The ratio of the resulting regioisomers is significantly affected by the structure of the starting compounds, which allows one to obtain products with a predominance of one regioisomer.

The review provides a brief historical background for the establishment of structure of benzofuroxanes. Methods for their synthesis are summarized, and the chemical properties are described, which are splitted into two parts: reactions proceeding with a ring opening of the heterocycle, and those occuring with a participation of the isocyclic moiety. The biological activity of various representatives belonging to the benzofuroxan series is covered in details.

The review presents and summarizes comprehensive data starting from 2000 on the synthesis of ureas containing alkylaromatic moieties. The advantages and drawbacks of various synthetic methods were highlighted. The biological activity was covered for some representatives of this class of compounds.

An efficient procedure has been developed for the synthesis diarylpropanes containing an urea fragment by acid-catalyzed reaction of N-(3,3-diethoxypropyl)ureas with sesamol. The product structure was proved by spectral data.

Short contacts play an important role in the formation of crystalline structures and stabilize the crystal packing. Short contacts involving S-atom of P = S-bonds and some C–H-bonds are formed in c...

International audience; The efficient approach to novel water-soluble 2-aryl-substituted N-(phosphorylmethyl)pyrrolidines via acid-catalyzed elimination/cyclization/Friedel–Crafts reaction sequence of {[(4,4-diethoxybutyl)amino]methyl}phosphonates is proposed. Zwitterionic structure of N-(phosphorylmethyl) pyrrolidines has been proved by X-ray crystallography.

The review presents and summarizes comprehensive data starting from 2006 on the synthesis of mono- and di-N-oxides of 2H-benzimidazoles and their chemical properties. Especial attention was paid to the chemical transformations of 2H-benzimidazole 1,3-dioxides upon heating to give 3H-2,1,4-benzoxadiazine 4-oxides and 2H-benzimidazole mono-N-oxides. The biological activity of compounds was covered.

A possibility to use pyridoxal as an alkylating agent in the reactions of electrophilic mono-, di-, and trisubstitution in the aromatic core of various phenols and polyphenols was demonstrated for the first time. New types of hydroxyl-containing aromatic aldehydes containing vitamin B6 fragment were obtained, and the conditions for their synthesis were optimized.

Reactions of pyridoxal hydrochloride with 5-pyrazolone derivatives in alcohol medium in the presence of concentrated hydrochloric acid led to the formation of new pyrazolones with pyridoxal fragments in the molecule. The corresponding diarylmethanes were formed when using pyridoxal and pyrazolone in a 1: 2 ratio.

New nitrogen-containing derivatives of pyridoxal were obtained as a result of its reaction with various amines. The reactions with amines bearing a heterocyclic fragment (pyridine, pyrimidine, quinoline, piperidine) furnished the final products stabilized in an aminoacetal form. The product prepared from 2-aminomethylpiperidine has an imidazolidine fragment in the molecule.

The reaction of 3-arylidene-1-pyrrolines with phenols yielded 2-arylpyrrolidines. The proposed method makes it possible to obtain pyrrolidines containing a phenol fragment in the position 2 in high yields and under mild conditions.

Adenine derivatives with a phosphorus-containing substituent on N9 have been synthesized, and their structure has been confirmed by 1H, 13C, and 31P NMR and IR spectroscopy, X-ray diffraction, MALDI mass spectrometry, and elemental analysis.

Dialkyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonates reacted with phenol and benzenediols in the presence of trifluoromethanesulfonic acid to give products of electrophilic substitution in the benzene ring, the corresponding diarylmethylphosphonates or [phenylenebis(arylmethylene)]- diphosphonates. The reaction of diphenyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate with 2-methylbenzene-1,3-diol at a ratio of 1: 1 afforded 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-6-hydroxy-7-methyl-2-phenoxy-2,3-dihydro-1,2λ5-benzoxaphosphol-6-one.

New salt structures have been synthesized from pyridoxal and various organic and inorganic acids.

The reaction of pyridoxal with 2,4-dihydroxybenzaldehyde in a hydrochloric acid solution gave 1-(5-formyl-2,4-dihydroxyphenyl)-7-hydroxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-5-ium chloride. Treatment of the latter with sodium hydride in ethanol afforded a free aldehyde in 85% yield. A series of azomethines and imidazolidines was obtained by reacting the obtained aldehyde with various amines and diamines.

4-Chloro-6-[1-(vinylsulfonyl)pyrrolidin-2-yl]benzene-1,3-diol prepared by the reaction of 2-ethoxypyrrolidine with 4-chlororesorcinol was introduced into the aza-Michael reaction with various amines which led to the formation of new 1-sulfonyl-2-arylpyrrolidines

Phosphonoethylated amino acetals were synthesized for the first time by reacting vinylphosphonates with α- and γ-aminoacetals. The reaction of 2-methylresorcinol with the acetals in ethanol in the presence of hydrochloric acid afforded the first representative of diarylbutylamines containing β-aminoethylenephosphoryl fragment.

Novel types of substituted framework phosphonates have been synthesized via functionalization of bicyclic compounds obtained in the reaction of 2-ethoxyvinyl dichlorophosphonate with different phenols. The reactions of functionalized bicyclic phosphonates with triphenyl phosphine have been studied; antimicrobial activity of the prepared compounds has been investigated.

Reactions of dialkyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonates with butyl, benzyl and propargyl alcohols in the presence of catalytic amounts of trifluoromethanesulfonic acid resulted in the formation of nucleophilic 1,6-addition products. Azide-alkyne cycloaddition reaction of dimethyl (3,5-di-tert-butyl-4-hydroxyphenyl)(prop-2-ynyloxy)methylphosphonate with benzyl azide and 1,3-bis-(2-azidoethoxy)benzene in the presence of copper sulfate and sodium ascorbate afforded 1,2,3-triazoles with sterically hindered phenol fragments.

New ethylenebisphosphorylated α-amino acetals were synthesized by the reaction of aminoacetaldehyde dimethyl acetal with ethenylidenebisphosphonates (Michael reaction). It was found that the synthesized compounds react with 2-methylresorcinol and resorcinol in the presence of HCl to form previously unknown diarylalkylammonium salts containing ethylidenebisphosphonate groups.

First specimens of 4-aryl-substituted tetrahydropyrimidin-2(1H)-ones containing a phosphoryl group were obtained through the reaction of 1-(3,3-diethoxypropyl)-1-[(dihexylphosphoryl)methyl]-3-phenylurea with resorcinol and its derivatives in the presence of trifluoroacetic acid.

The reaction of 2-hydroxy-5,7,8-trimethyl-2-oxobenzo[e]-1,2-oxaphosphorine with thionyl chloride yielded the pyrophosphonate product, which was isolated and characterized for the first time. Subsequent treatment of it with phosphorus pentachloride led to the formation of new types of unsymmetrical cage phosphonates.

An efficient procedure has been developed for the synthesis of macroheterocycles by acid-catalyzed reaction of N,N′-(1,4-phenylene)bis[N′-(4,4-diethoxybutyl)urea] with resorcinol, 2-methylresorcinol, and pyrogallol. The structure of the isolated compounds was proved by spectral methods.