Idris M. Akhmedov

Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds

2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into β-enamino, β-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared in good yield.

Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones

Abstract Mn(OAc)3 oxidation of aromatic ketones afforded the α-acetoxy ketones in good yield. Selective hydrolysis of the acetoxy ketones by the fungus Rhizopus oryzae yields (R)-hydroxy ketones in high enantiomeric excess.

The synthesis of chiral 5-methylene pyrrol-2(5H)-ones via photooxygenation of homochiral 2-methylpyrrole derivatives

Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amines, amino alcohols and amino acid esters. The photooxygenation of these pyrrole derivatives in the presence of a photosensitiser furnishes the corresponding α,β,γ,δ-unsaturated γ-lactams as the major products in good yields.

Synthesis and characterization of waterborne and phosphorus-containing flame retardant polyurethane coatings

Phosphorus-containing flame retardant water-dispersed polyurethane coatings were produced by incorporating different amounts of a phosphorus compound onto the polyurethane main chain. The novel phosphorus containing compound (phosphorus phenyl dihydroxy) was synthesized in three steps using benzaldehyde, pentaerythritol, phenyl phosphonic dichloride, and acetic acid.The addition of phosphorus phenyl dihydroxy to the main chain of polyurethane, in which NCO/OH ratio was kept constant at 1.5 and the amount of dimethylolpropionic acid (DMPA) at 3.5 wt%, increased the hardness and abrasion resistance, but only slightly decreased the gloss values of the polyurethane paints. All the samples showed superior impact resistance and flexibility. Moreover, increasing the phosphorus content increased the char yield, and the maximum fire retardancy was reached at 1.5% P content with a limiting oxygen index (LOI) value of 29.

Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-methylpyrrole derivatives

Abstract 5-Chloro-3-penten-2-one reacts with the amino group of homochiral amines, amino alcohols, amino acid esters to form corresponding 2-pyrrole derivatives in good yield and without racemization.

Hexachlorocyclopentadiene in diels—alder asymmetric reaction

Abstract Asymmetric thermal Diels—Alder reactions with chiral dienophiles l-menthyl acrylate and l-menthyl allyl ether, using hexachlorocyclopentadiene (HCC) gave cycloadducts of up to 150%ee. Milder reaction conditions achieved by the use of Lewis acid catalysis increased the optical yields up to 2.8 fold. The catalyzed and uncatalyzed reactions using l-menthyl acrylate result in the formation of adducts having opposite configurations. The products have also been resolved via diastereomer formation as pure enantiomers.

Resolution of (±)-2-substituted norbornadiene and hexachloronorbornadiene derivatives using CCL and PLE

Abstract (±)-2-Hydroxymethylbicyclo[2.2.1]hepta-2,5-diene, (±)-2-acetoxymethylbicyclo[2.2.1]hepta-2,5-diene and their hexachlorinated derivatives were resolved via CCL- and PLE-catalysed hydrolysis to afford enantiomerically enriched products with e.e.s of 61–93%. The absolute configurations were determined by transforming 2-hydroxymethylbicyclo[2.2.1]hepta-2,5-diene into the 2-formylbicyclo[2.2.1]hepta-2,5-diene with known absolute configuration.

Reactions of 2-Substituted Epichlorohydrins

Abstract 2-Substituted epichlorohydrins have been synthesized by starting with 1,2-dichloro acetone and various alkyl and aryl halides via dichlorohydrins followed by cyclization. The reactive 2-substituted epichlorohydrins were subjected to nucleophilic attacking of azide and cyanide ions to afford corresponding β-azido alcohols and α,β-unsaturated nitriles.

Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-substituted pyrrole derivatives

The conversion of the amino group of chiral amines, amino alcohols, amino acids and their esters into chiral 2-substituted pyrrole derivatives with various halogeno enones is described. The conversion works in good yield and without racemization. The synthesis of 2-phenylpyrrole derivatives was possible with amino alcohols but not with amino acids or their esters.

Asymmetric Ene Reactions of 2-Methylpropene with Chloroaldehydes in the Presence of Borontrifluoride-l-menthylethyl Etherate

Abstract The asymmetric ene reactions of prochiral chloroaldehydes, chloral and 2,3-dichlorobutanal with 2-methylpropanal in the presence of BF 3 l-menthylethyl etherate gave optically active homoallylic alcohols in 16–22% ee. The dechlorination of the chloro alcohols lead to the unsaturated derivatives of alcohols.