Imidazoline Derivatives with Nucleophilic Reagents

Interaction of Imidazoline Derivatives with Nucleophilic Reagents 

The presence of the reactive nitrone group in the molecule of the 3-imidazoline-3-oxide heterocyle is responsible for the course of reactions of 1,3-bipolar addition. The interaction of 1-hydroxy-2,2,5,5-tetramethyl- 

3-imidazoline-3-oxide (6d) with potassium cyanide in water leads to the formation of l-hydroxy-2,2,5,5-tetramethyl-3-imidazoline-4-carboxylic acid amide (30). Addition to the nitrone group is accompanied by dehydration and partial hydrolysis of the nitrile group (Volodarsky et a/., 1971). Oxidation of amide 30 gives nitroxide 31 and hydrolysis leads to the respective salt 32, from which free acid 33 was obtained. 

Addition of hydrocyanic acid to the electron-deficient immonium group proceeds easily. Treatment of aqueous solutions of 3-imidazolinium methyl sulfates (24a,b) with a solution of an equimolecular quantity of 

Interaction of 3-imidazoline-3-oxide nitroxides with Grignard reagent proceeds with the involvement of the radical center and leads to reduction products 6a,c and methoxy derivatives 35a,c. Meanwhile, in the interaction of methylmagnesium iodide with the methoxy derivatives 1,3-addition to the nitrone group occurs, and 1-methoxy-3-hydroxy-4-alkyl (aryl)- 

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