C- and O-Alkylation with α-Haloketones of the Adamantane Series

Reactions of 1-adamantyl bromomethyl ketone and 1-(1-adamantyl)-3-bromo-2-propanone with acetylacetone and ethyl acetoacetate in a mixture of dry diethyl ether with anhydrous methanol in the presence of sodium methoxide afforded 3-(1-adamantylcarbonylmethyl)-2,4-pentanedione, ethyl 2-(1-adamantylcarbonylmethyl)-3-oxobutanoate, 4-acetyl-1-(1-adamantyl)-2,5-hexanedione, and ethyl 2-acetyl-5-(1-adamantyl)-4-oxopentanoate. The Knoevenagel-Cope reactions of 1-adamantyl bromomethyl ketone and 1-(1-adamantyl)-3-bromo-2-propanone with diethyl malonate yielded, respectively, diethyl 1-(1-adamantyl)-2-bromoethylidenemalonate and diethyl 1-(1-adamantylmethyl)-2-bromoethylidenemalonate. O-Alkylation of ethyl acetoacetate with 1-adamantyl bromomethyl ketone gave ethyl 3-(1-adamantylcarbonylmethoxy)-2-butenoate. Carboxylic acids reacted with 1-adamantyl bromomethyl ketone to form the corresponding 2-(1-adamantyl)-2-oxoethyl carboxylates.     

Reactions of 1-Cyanoimidazoles with Phenols

Phenols with pK _a 7 react with 1-cyanoimidazole and 1-cyano-2-methylimidazole to give addition products at the cyano group; phenols with pK _a 1 give rise to the corresponding quaternary salts, 1-cyanoimidazolium phenolates; phenols with pK _a 4 do not react with 1-cyanoimidazoles.     

Synthesis,Application, and Properties of Bis(1H-azol-1-yl)methanimines

Russian Journal of Organic Chemistry - The review considers methods of preparation and application of bis(1H-azol-1-yl)methanimines that are imino analogs of 1,1′-carbonylbisazoles widely...     

Synthesis of 4-(1<Emphasis Type="Italic">H</Emphasis>-Azol-1-ylmethyl)benzohydrazides and Their Acyclic and Heterocyclic Derivatives

4-(1H-Azol-1-ylmethyl)benzohydrazides were prepared from methyl 4-(bromomethyl)benzoate, azoles, and hydrazine hydrate. Reactions of 4-(1H-imidazol-1-ylmethyl)benzohydrazide with carbonyl compounds gave hydrazones whose tautomerism was studied. From the hydrazides, 1,3,4-oxadiazoles, 1,2,4-triazole- 5-thione, and N-benzoyl-N′-alkyl(aryl)sulfonylhydrazines were synthesized.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 1, 2005, pp. 123–129.Original Russian Text Copyright © 2005 by Osyanin, Purygin, Belousova.     

Reaction of N,N-dimethylaniline with N-cyanoazoles according to electrophilic aromatic substitution pattern

Russian Journal of Organic Chemistry -     

Relationship of energy characteristics and the Randic indices of imidazole and some azolides of sulfonic acids with chromatographic retention

Imidazole and some newly synthesized imidazolides and triazolides of sulfonic acids were investigated by reversed-phase chromatography. The Randic indices, the total energies of molecules, and the energies of the transition states to hydrolysis of imidazolides and triazolides in a neutral medium were calculated. Correlations between these parameters and the retention factors were elucidated. Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1401–1404, August, 2000.