A. Yu. Fedorov

Synthesis and structures of the six-coordinate donor-acceptor complexes R3(C6H4O2)Sb…L (R=Ph, L=OSMe2 or ONC5H5; R=Me, L=ONC5H5 or NC5H5) and R3(C2H4O2)Sb…L (R=Ph, L=ONC5H5; R=Cl or C6F5, L=OPPh3)

One-pot oxidation of R3Sb (R=Ph, Me, Cl, or C6F5) withtert-butyl hydroperoxide in the presence of 1,2-diols and monodentate donor compounds was studied. The structures of the resulting neutral organic donor-acceptor SbV complexes, Ph3(C6H4O2)Sb…OSMe2, Ph3(C6H4O2)Sb…ONC5H5, Me3(C6H4O2)Sb…ONC5H5, Me3(C6H4O2)Sb…NC5H5, Ph3(C2H4O2)Sb…ONC5H5, and Cl(C6F5)2(C2H4O2)Sb…OPPh3, were established by X-ray diffraction analysis. In these complexes, the coordination environment about the Sb atoms is a distorted octahedron. The Sb−O(N) distances and the Sb−O−E angles (E=S, N, or P) vary over wide ranges.

Catalytic methods of creation and functionalization of the coumarin skeleton

Methods of synthesis and functionalization of coumarins using metal complex and organic catalysis are considered in the review.

Organic chemistry. History and mutual relations of universities of Russia

The review describes the history of development of organic chemistry in higher schools of Russia over a period of 170 years, since the emergence of organic chemistry in our country till now.

Novel water-soluble anticancer agents derived from 4-arylcoumarins

Novel 4-arylcoumarin derivatives were obtained. They are water-soluble analogs of the well-known anticancer drug combretastatin A-4. The key step of the synthesis involves the Suzuki-Miyaura cross-coupling. The water-soluble salts obtained exhibit considerable cytotoxic activity against the HBL-100 and HaCaT cell lines.

Synthesis of (azidomethyl)phenylboronic acids

The synthesis of 2-, 3-, and 4-(azidomethyl)phenylboronic acids was carried out. The geometric and electronic structures were studied by quantum-chemical methods. The suggestion is made that there are weak intramolecular interactions between the boron atom and the nitrene nitrogen atom of the azido group.

N- and O-arylation with triphenylantimony ortho-phenylenedioxides

Abstract2,2,2-Triphenyl-1,3,2-benzodioxastibolanes react with alcohols, phenols, and amines in the presence of copper salts to give the corresponding O- and N-phenyl derivatives. Cyclic SbV dialkoxide containing an electron-withdrawing nitro group in the dioxastibolane fragment is most reactive in N-phenylation of primary and secondary amines. Organoantimony analogs containing electron-donating groups are more efficient in O-phenylation of primary and secondary alcohols and phenols.

Syntheses of antimony(v) derivatives from trimethyl and triphenylantimony(III), dihydric phenols, andtert-butyl hydroperoxide

Trimethyl and triphenylantimonyo-phenylene dioxides were obtained by the reaction of trimethyl- and triphenylantimony with pyrocatechol in the presence oftert-butyl hydroperoxide in 68 and 81 % yields, respectively. 7,7,7,15,15,15-Hexamethyl-(and phenyl)-6,8,14,16-tetraoxa-7, 15-distibatricyclo[11.3.1.19,13]octadeca-1,3,5,9,11,13-hexaenes were synthesized analogously by the reaction with resorcinol (in 79 and 93 % yields, respectively). The use of hydroquinone resulted in polymeric trimethyl- and triphenylantimony hydroquinolates.

Modern Trends of Organic Chemistry in Russian Universities

This review is devoted to the scientific achievements of the departments of organic chemistry in higher schools of Russia within the past decade.

2-(Azidomethyl)phenylboronic acid in the synthesis of isoquinoline derivatives

Abstract2-(Azidomethyl)phenyllead triacetate was obtained by the reaction of 2-(azidomethyl)phenylboronic acid with lead tetraacetate. A strategy for the synthesis of isoquinoline derivatives was proposed that involves a reaction of this organolead reagent with enolizable substrates followed by annelation in the presence of triphenylphosphine. The use of 2-(azidomethyl)phenylboronic acid allowed α-arylation products to be obtained from β-diketones and natural β-oxo lactones in good yields.

Synthesis of new sulfur-containing derivatives of furanoallocolchicinoids

Reaction of hydroxyl-containing heterocyclic colchicinoids with S-nucleophiles led to the formation of furanoallocolchicinoid sulfides in a high yield.