Reactions of 2,2-dimethyl-3-phenylazirine with hydrazino and amino alcohols

Abstract

The reaction of 2,2-dimethyl-3-phenylazirine with β-hydrazino alcohols leads to the corresponding β-hydroxyalkylhydrazones of 2-amino-2-methyl-1-phenyl-1-propanone. The reaction of the same azirine with β- and γ-amino alcohols gives primarily substituted oxazolidines and perhydro-1,3-oxazine, respectively, which undergo isomerization to the chain form, viz., the corresponding N-(2-amino-2-methyl-1-phenylpropylidene)amino alcohols; the tendency to undergo isomerization to the chain form is not manifested in the case of β-aminoethanol. A conclusion regarding the preferred conformation of the oxazolidines was drawn on the basis of the data from ¹H and ¹³C NMR spectroscopy. The product of the reaction of azirine with α-aminoethanol is 2,5,5-trimethyl-4-phenyl-3-imidazoline.