Vera L. Mamedova

A novel acid-catalyzed rearrangement of 2-substituted-3-(2-nitrophenyl)oxiranes for the synthesis of di- and mono-oxalamides

A novel one-pot synthetic approach to N1-(2-carboxyaryl)-N2-(aryl or H)oxalamides from 3-(2-nitroaryl)oxirane-2-carboxamides via the classical Meinwald rearrangement and a new rearrangement sequence has been developed. The methodology is applicable to the synthesis of N-(2-carboxyphenyl)aryloxalmonoamides from (3-(2-nitrophenyl)oxiran-2-yl)(aryl)methanones. The method is operationally simple and high yielding, thus providing a new useful formula for both anthranilic acid derivatives and oxalamides.

The Meinwald rearrangement in tandem processes (microreview)

The Meinwald rearrangement refers to the process of conversion of epoxides to carbonyl compounds, accompanied by the migration of one of the substituents of the epoxide ring. In this microreview, literature concerning the Meinwald rearrangement in tandem processes from 2012 to the present is surveyed. Tandem processes in this review are interpreted as one-pot processes that represent a set of reactions taking place without changing the conditions during the experiment.

Synthesis of 5-[bromo(aryl)methyl]-2,2-dimethyl-1,3-oxazolidin-4-ones

A Darzens condensation of α-chloroacetamide with aromatic aldehydes furnished a series of 3-aryl-2,3-epoxypropionamides, which were further converted to 5-[bromo(aryl)methyl]-2,2-dimethyl-1,3-oxazolidin-2-ones.

Transformations of anilides of 3-aryl-2,3-epoxypropionic acids when exposed to acidic agents

Anilides of 3-aryl-2,3-epoxypropionic acids on treatment with aqueous HBr gave 3-aryl-3-bromo-2-hydroxypropionic acid anilides and (in some cases) 2-bromo-3-hydroxy regioisomers. Cyclization of these products into 3-arylquinolin-2(1H)-ones was studied.

New hydrophosphoryl compounds derived from ent -16-oxobeyeran-19-oic acid

A number of 16-hydroxy derivatives were obtained from ent-16-oxobeyeran-19-oic acid, O-phosphorylation of which with subsequent hydrolysis led to the corresponding hydrophosphoryl compounds. Their diastereomeric composition was studied.

Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation – Friedel-Crafts Alkylation Strategy

The new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones through the Darzens condensation (epoxidation) of dichloroacetanilides with aromatic aldehydes followed by one-pot dechlorative epoxide-arene cyclization is described. This methodology has been utilized for the synthesis of naturally occurring viridicatol, a fungal metabolite isolated from the penicillium species.

5-(α-Halobenzyl)- and 5-Benzylidene-2,2-dimethyl-1,3-oxazolidin-4-ones in Synthesis of α-Hydroxy Acids

The reactions of acid hydrolysis of 5-(α-halobenzyl)- and 5-benzylidene-2,2-dimethyl-1,3-oxazolidin-4-ones were studied. A possibility of the synthesis of corresponding α-hydroxy acids was shown.

First coordination polymer based on diterpenoids. Synthesis, structure, and magnetic properties

One-dimensional coordination polymer was obtained by cation exchange reaction of triethylammonium salt of methyl ent-16α-H-phosphonyloxybeyeran-19-oate with CuCl2. Its structure was determined by single crystal X-ray diffraction analysis. The formation of hydrophilic channels consisting of phosphorus containing fragments, copper atoms, and water, which are framed by hydrophobic surroundings from tetracyclic bulky beyeran substituents, is observed in the crystal. The study of the temperature dependence of the static magnetic susceptibility of the polymer indicates a weak antiferromagnetic interaction between the copper spins.