Synthesis of Peroxide Monomers Based on Unsaturated Carboxylic Acids

Russian Journal of Organic Chemistry -     

Mild and Efficient Synthesis of Carboxylic Acid Anhydrides from Carboxylic Acids and Triazine Coupling Reagents

Abstract

Anhydrides of carboxylic acids were obtained in 53%–95% yield by treatment of appropriate carboxylic acids with 2‐chloro‐4,6‐dimethoxy‐1,3,5‐triazine (CDMT) or 2,4‐dichloro‐6‐methoxy‐1,3,5‐triazine (DCMT) in the presence of N‐methylmorpholine. It has been proved that synthesis proceeds via triazine active esters 3a,b, which are able to acylate carboxylate anion but not less nucleophilic carboxylic acid.     

Catalytic Ketonization of Carboxylic Acids Synthesis of Saturated and Unsaturated Ketones

Activity of 20wt% MO₂/Al₂O₃ catalysts, where M = Mn, Ce and Zr has been studied in ketonisation of the mixtures of propanoic/pentanoic, ethanoic/10-undecenoic and hexanoic/(Z)-9-octadecenoic (oleic) acids. Irrespective of the molecular weights and molar ratios of reacting acids, high yields of ketones were obtained over Mn and Ce oxide catalysts at approximately 673 K. Isomerization of C=C double bonds and partial pyrolysis occurred during catalytic ketonization of 10-undecenoic and oleic acids, diminishing slightly the yield of ketones. The preparation of (Z)-14-tricosen-6-one has been performed, being the starting material for the synthesis of (Z)-9-tricosene - sex attractant of male house fly.     

Dianions of Unsaturated Carboxylic Acids in Synthesis. Synthesis of Juvocimene I

Juvocimene I is prepared by a non ambiguous synthesis based on the regioselective alkylation of 4-methylhexa-2,4-dienoic acid, and Wittig olefination of the aldehyde corresponding to the alkylated acid.     

New Conjugates of Di- and Trichlorocyclopentenones with Amino Derivatives of Adamantane and Amino Acids

Reactions of di- and trichlorocyclopentenones with adamantan-1-amine, 1-(adamantan-1-yl)ethanamine, and amino acids (histidine, L-proline, L-methionine methyl ester hydrochloride) afforded the corresponding enamino ketones.     

Synthesis of Aminoalcohols of the Adamantane Series

The reduction of - and -aminoketones and enaminoketones of the adamantane series with sodium borohydride in methanol at room temperature gives the corresponding adamantylaminoalkanols.     

Microwave-Assisted Esterification of Diverse Carboxylic Acids and Chiral Amino Acids

A facile and efficient synthetic method of esters from their corresponding carboxylic acids and amino acids is described. The esterification reaction of carboxylic acids and amino acids could be greatly accelerated under microwave irradiation because the reactions described in this article took place in only 5 min with almost quantitative yields, and distinct acidity of catalytic acids was well tolerated. Unlike the racemation problem in microwave-assisted N-acylation reactions, the esters of chiral amino acids could be achieved with retention of configuration under this condition.     

Dienediolates of Unsaturated Carboxylic Acids in Synthesis. Tandem Michael Diechmann Synthesis of Substituted 2-Cyclohexenones

3,5-Disubstituted 2-Cyclohexenones are prepared by tandem Michael-Dieckmann addition of lithium dienediolates of dimethylacrylic and β-methylcinnamic acids to lithium carboxylates of unsaturated carboxylic acids.     

Synthesis and Cyclization of Diketones from the Adamantane Series

Cyclic - and -diketones of the adamantane series were synthesized by reactions of chlorides of 1-adamantanecarboxylic acids and 1-adamantyl bromomethyl ketone with cyclic enamines 1-morpholino-1-cyclopentene and 1-morpholino-1-cyclohexene. Cyclization of the -diketones obtained was performed by reaction with hydroxylamine and phenylhydrazine.     

Synthesis and Reactivity of Aldehydes of the Adamantane Series

1-Adamantanecarbonitriles are very active in the Stephen reaction, which allows synthesis of the corresponding aldehydes in high yields. Electron-acceptor substituents in the 3 position of the adamantine nucleus exert almost no effect on the yield of aldehydes. Separation of the nitrile group and the adamantane nucleus by one methylene group results in a complete loss of reactivity. A quantitative study of the reactivity of the synthesized aldehydes in the oximation reaction was performed.     

Synthesis of Ph3Bi(O2CR)2 Compounds with Unsaturated Carboxylic Acids and Use of Triphenylbismuth Dicrotonate in the Synthesis of Bismuth-Containing Polymers

Russian Journal of General Chemistry - Triphenylvismuth dicarboxylates Ph3Bi(O2CCH=CHMe)2, Ph3Bi(O2CCH=CHPh)2, Ph3Bi(O2CCH=CHC6H4NO2-m)2, Ph3Bi(O2CCH=CHC4H3O)2, Ph3Bi(O2CCH=CHC6H4OMe-p)2,...     

Novel Organophosphorus Reagents for the Synthesis of Amines

Abstract:

New organophosphorus equivalents of a² type N-protected amine synthons are presented.     

Synthesis of β-Aminoketones of the Adamantane Series

4-(1-Adamantyl)-1-aminobutan-3-one hydrochlorides were synthesized by the Mannich reaction of (1-adamantyl)acetone with paraformaldehyde and secondary amine hydrochlorides (diethylamine, dibenzylamine, piperidine). Analogous reactions of 1-adamantyl(methyl)amine with acetone, p-hydroxyacetophenone, and methyl 2-thienyl ketone gave 1-[(1-adamantyl)methylamino]propan-3-one hydrochlorides.     

低能氮离子诱发氨基酸前生物合成反应的初步研究

利用氮气火花放电产生离子 ,其中的正离子在阴极位降的加速下“注入”到三种羧酸盐的水溶液中 ,诱发其中的化学反应并沉积在水溶液中 .利用高效液相色谱 (HPLC)对离子注入后的样品进行分析 ,结果表明 ,氮离子注入可使氮沉积在溶液中 ,生成氨及氨基酸 ,这一结果不仅验证了低能离子注入样品时的“质量沉积”效应 ,而且还是原始地球条件下氨基酸生成的一种可能的途径     

Intramolecular Fluorocyclizations of Unsaturated Carboxylic Acids with a Stable Hypervalent Fluoroiodane Reagent

A new class of fluorinated lactones was prepared by the intramolecular fluorocyclizations of unsaturated carboxylic acids by using the stable fluoroiodane reagent in combination with AgBF₄. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step. The fluoroiodane reagent, prepared easily from fluoride, can also be used without a metal catalyst to give moderate yields within just 1 hour, thus demonstrating that it is a suitable reagent for developing new ¹⁸F‐labelled radiotracers for PET imaging.