Synthesis and Structure of Mixed Phosphonium-iodonium Ylide

A mixed phosphonium-iodonium ylide, phenyliodoniumethoxycarbonylmethylenetriphenylphosphorane borofluoride, was synthesized. Its structure was established by means of X-ray diffraction analysis. Temperature dependence of ¹H, ¹³C, and ³¹P spectra of the ylide synthesized was investigated. A dynamic equilibrium between Z and E-isomers was observed.     

Three-component catalytic method for synthesis of α-amino phosphonates with the use of α-amino acids as amine component

Interaction of aliphatic and aromatic aldehydes and ketones with optically active L-α-amino acids or their esters in the three-component catalytic one-pot synthesis of α-aminophosphonates was studied. The corresponding α-amino phosphonates are formed in high yields as mixtures of diastereomers. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 768–774, April, 2007.     

Regioselective heterocyclization of mixed phosphonium-iodonium ylides with acetylenes involving dimethyl acetylenedicarboxylate

Russian Chemical Bulletin - A new approach to the synthesis of λ5-phosphinolines was developed consisting in the reaction of mixed phosphonium-iodonium ylides with acetylenes in the presence...     

Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex as a reagent for preparation of carboxylic acid bromides

Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex was successfully used as a new reagent for the synthesis of carboxylic acid bromides which were isolated as individual substances or were identified by conversion into the corresponding anilides. The reaction is chemoselective, and it can be applied to polyfunctional compounds, e.g., hydroxy acids.Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 10, 2004, pp. 1517–1521.Original Russian Text Copyright © 2004 by Matveeva, Podrugina, Sandakova, Zefirov.     

Benzoylhydrazones in catalytic hydrophosphorylation

Reactions of benzoylhydrazones derived from heterocyclic and aromatic aldehydes and aliphatic, heterocyclic, and aliphatic-aromatic ketones with diethyl phosphite in the presence of [tetra(tert-butyl)phthalocyanine]aluminum chloride afford α-benzoylhydrazino phosphonates in high yields.     

Aggregation properties of copper dibenzo-barrelenophthalocyanine

Depending on the solvent in which they are placed or from which they have been obtained, sterically hindered copper octa-tert-butyltetra-4,5-dibenzobarrelenophthalocyanines in solution and as a powder can take a monomeric form or dimer or trimer aggregate forms. In the aggregates, the molecules are disposed opposite one another around a high-order axis at an angle of 45° from equatorial displacement.Institute for the Chemistry of Natural Organic Materials, Russian Academy of Sciences, Krasnoyarsk 660000. Scientific-Research Institute for Organic Itermediates and Dyes, Moscow 103787. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 171–175, February, 1995. Original article submitted December 22, 1994.     

Synthesis and photophysical properties of conformationally fixed tricarbocyanines with phosphonate groups

A method for the synthesis of a series of symmetric and asymmetric conformationally fixed tricarbocyanines was developed based on benzоindolenine containing ethyl phosphonate and diethyl phosphonate groups in the linker at the quaternary nitrogen atom of the indolenine fragment. The polymethine chain meso position was modified by nucleophilic substitution of chlorine with O- and N-nucleophiles. Their absorption and fluorescence spectra were recorded, the possibility of further use of phosphonate-substituted tricarbocyanines as biomarkers was demonstrated. The dark cytotoxicity of synthesized compounds was studied, the possibility of their accumulation in HCT116, MCF7 cancer cells was shown.     

Aminopyridines as amino components in the catalytic synthesis of α-aminophosphonates

6h-Aminophosphonates containing alicyclic, aromatic, and heterocyclic fragments were obtained in high yields by the Kabachnick—Fields reaction of the corresponding carbonyl compounds with 2-, 3- and 4-aminopyridines and diethyl phosphite using tetra- tert-butyl- phthalocyanine aluminum chloride as the catalyst. 2-, 3-, 4-Aminopyridines were found to vary in their reactivity with ketones and diethyl phosphite in the catalytic three-component one-pot process.     

Mixed iodonium-, phosphonium-, arsonium-, sulfoniumdiazonium ylides in reactions with nucleophiles

Russian Chemical Bulletin - The reactions of mixed ylides containing a diazonium fragment and an "onium" group of different nature with nucleophiles were studied. In the...     

Syntheses of Compounds Active toward Glutamate Receptors: II. Synthesis of Spiro Hydantoins of the Indan Series

The article describes a general procedure for synthesizing hydantoins of the indan series, which makes it possible to obtain bioisosteric analogs of 1-aminoindan-1,5-dicarboxylic acid, a group I metabotropic glutamate receptor antagonist.