Catalyst-Free Annulation of Acylethynylpyrroles with 1-Pyrrolines: A Straightforward Access to Tetrahydrodipyrrolo[1,2-:1',2'-]imidazoles.

Acylethynylpyrroles undergo facile (rt, MeCN or MeOH, 24-72 h) catalyst-free annulation with 1-pyrrolines to afford acylmethylenetetrahydrodipyrrolo[1,2-:1',2'-]imidazoles in up to 93% yield and 90% -stereoselectivity of the olefin moiety.

Cyanoquinolines and Furo[3,4-]quinolinones Formation via On-The-Spot 2,3-Functionalization of Quinolines with Cyanopropargylic Alcohols.

A convenient approach to 2-(1-ethoxyalkoxy)-3-cyanoquinolines (in up to 50% yields) has been developed. The approach comprises functionalization of quinolines with acetals of cyanopropargylic alcohols (KOH/HO/MeCN, 55-60 °C) followed by their transformation to furo[3,4-]quinolinones (in up to 98% yields) via the sequential removal of acetal protection and intramolecular cyclization/hydration (7% aqueous HCl, acetone, 20-25 °C).

The New Pharmaceutical Compositions of Zinc Oxide Nanoparticles and Triterpenoids for the Burn Treatment.

We studied oleogels containing zinc oxide nanoparticles (ZnO NPs) and lupane triterpenoids in sunflower oil for the treatment of burns. The modification of ZnO was carried out by treatment with alcohol solutions of betulin, betulonic acid, betulin diacetate and betulin diphosphate. The properties of modified ZnO NPs were studied by powder XRD (average sizes of 10-20 nm), FTIR (νZnO 450 cm), UV-vis (345-360 nm), and blue-violet emission (380-420 nm).

Acylacetylenes in multiple functionalization of hydroxyquinolines and quinolones.

The expected one-pot multiple functionalization of hydroxyquinolines and quinolones with acylacetylenes (20 mol% KOH, 5 equiv. HO, MeCN, 55-60 °C), which, according to the previous finding, might involve the addition of OH and NH-functions to the triple bond and insertion of acylacetylenes into the quinoline scaffold, retains mainly on the formation of chalcone-quinoline ensembles in up 99% yield. The higher functionalized quinolines can be obtained in a synthetically acceptable yield, when the above ensembles are treated with the second molecule of acylacetylenes.

Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF-ynones and Base-Induced Rearrangement.

The reaction of quinolines with CF-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield.

One-Pot Metal-Free Synthesis of 3-CF-1,3-Oxazinopyridines by Reaction of Pyridines with CFCO-Acetylenes.

The reaction of pyridines with trifluoroacetylated acetylenes was investigated. It was found that the reaction of various pyridines with two molecules of CFCO-acetylenes proceeds under mild metal-free conditions. As a result, efficient stereoselective synthesis of 3-arylethynyl-3-trifluoromethyl-1,3-oxazinopyridines was elaborated.

Cyanoacetylenes as Triggers and Partners in KOH-Assisted Assemblies of Quinoline-Based Dihydropyrimido[1,2-]quinolin-3-ones on Water.

Arylcyanoacetylenes trigger the assembly of dihydropyrimido[1,2-]quinolin-3-ones in good to excellent yields on the platform of quinolines in the presence of KOH in aqueous media at room temperature. This green on-water methodology provides a simple one-pot access to a novel family of the pharmaceutically prospective compounds.

Betulin-3,28-diphosphate as a Component of Combination Cytostatic Drugs for the Treatment of Ehrlich Ascites Carcinoma In Vitro and In Vivo Experiments.

The activity of betulin-3,28-diphosphate (BDP) in combination with the cytostatics such as 5-fluorouracil (5-FU) and hydrazine sulfate (HS) was demonstrated by using the transplanted Ehrlich ascites carcinoma (EAC) in mice. The dose-dependent effect of combination drugs BDP + HS and BDP + 5-FU was revealed by in vitro experiments on rats. The synergetic effect of HS and BDP on oxidative stress and energy metabolism was established.

Stereoselective tandem ring opening of imidazoles with electron-deficient acetylenes and water: synthesis of functionalized (Z,Z)-1,4-diaza-2,5-dienes.

1-Substituted imidazoles undergo exceptionally facile stereoselective ring opening under the influence of electron-deficient acetylenes and water (equimolar ratio of the reactants) in MeCN at 45-60 °C without any catalysts to afford functionalized (Z,Z)-1,4-diaza-2,5-dienes, (Z,Z)-propenylaminoethenylformamides, in up to 80% yields. The reaction is rationalized to proceed in a tandem manner via zwitterionic vinyl carbanions formed by nucleophilic addition of imidazole to the triple bond. The carbanionic center is then quenched with water followed by the rearrangement of the intermediate 2-hydroxy-3-alkenylimidazolines.

A general synthetic strategy for the design of new BODIPY fluorophores based on pyrroles with polycondensed aromatic and metallocene substituents.

BODIPYrrole: A general strategy for the design of novel BODIPY fluorophores based on pyrroles with polycondensed aromatic and metallocene substituents has been developed. The strategy involves the acylation of the condensed substituent and treatment of the acylated derivative (as oxime) with acetylene in MOH/DMSO (M = alkali metal) to give pyrroles that were then used for assembly of the BODIPY fluorophores (see scheme).

Stereoselective C(2)-vinylation of 1-substituted imidazoles with 3-phenyl-2-propynenitrile.

First examples of direct vinylation of 1-substituted imidazoles at the 2-position of the imidazole nucleus are described. 1-Substituted imidazoles 1a-e are C(2)-vinylated with 3-phenyl-2-propynenitrile (2) at room temperature without catalyst and solvent to afford 3-(1-organyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitriles 3a-e, mainly (c.a.