I. A. Motorina

Synthesis of hydroxyisoxazolidines on adsorbents

Abstract 3- And 5-hydroxyisoxazolidines can be synthesized in solution and on the surface of an adsorbent. The regioselectivity depends on the type of adsorbent used.

Synthesis of isoxazolidine derivatives from N-substituted hydroxylamines and α,Β-unsaturated ketones

The reaction of methyl vinyl ketone with N-Phenyl-hydroxylamine leads to a tautomeric mixture of 5-hydroxy-2-phenyl-5-methylisoxazolidine and its linear form, while the reaction with benzohydroxamic acid leads to linear products of addition to the oxygen or nitrogen atoms, depending on the reaction conditions. The first representatives of 5-hydroxyisoxazolidines with the residue of an aliphatic carboxylic acid attached to the nitrogen atom were obtained by acylation of 5-hydroxy-3,3,5-trimethylisoxazolidine.

Interaction of 5-hydroxypyrazolidines with Ch-acid compounds

The interaction of I-acetyl-2 phenyl-5-hydroxypyrazolidine with carbonyl compounds on the surface of acidic aluminum oxide results in the formation of products in which the hydroxyl group has been replaced by the residue of the carbonyl compound. It has been shown that derivatives of ß-dicarbonyl compounds, under the conditions of the reaction, may undergo subsequent conversions in which one of the carbonyl-containing residues is split off.

SYNTHESIS AND PROPERTIES OF FUNCTIONALLY SUBSTITUTED 1,2- AZOLIDINES

Results of investigations on the synthesis and properties of functionally substituted 1,2-azolidines are reviewed.

Synthesis of hydroxyisoxazolidines on the surface of adsorbents

The reaction of arylhydroxamic acids with α, Β-unsaturated carbonyl compounds on the surface of adsorbents without a solvent leads, depending on the properties of the adsorbent, to the formation of 2-aroyl-3-hydroxyisoxazolidines and/or 2-aroyl-5-hydroxyisoxazolidines. Reactions on the surface of silica gel and di- and triethylaminoethylcellulose proceed regioselectively.

Acid-base characteristics of 2-acyl-3(5)-hydroxyisoxazolidines in a hydrogen bond

In solution hydroxyisoxazolidines form intermolecular hydrogen bonds. For 3-hydroxyisoxazolidines the proton acceptor is the oxygen atom of the hydroxyl group, and for the 5-hydroxy compounds it is the cyclic oxygen atom. These compounds are close to phenol with respect to the relative acidity in the hydrogen bond.

Spatial structure of 2-benzoyl-3-methoxy-5-methylisoxazolidine

The nuclear Overhauser effect and x-ray diffraction analysis have been employed to determine the spatial structure of the diastereoisomeric 2-benzoyl-3-methoxy-5-methylisoxazolidines. It has been found that the predominant isomer in the reaction mixture has the cis-configuration.