Synthesis and study of properties of azoles and their derivatives - Communication 22. Syntheses based on 1-adamantanecarbonitrile

Article abstract of DOI:10.1007/BF00922328

1. 1-Adamantanecarbonitrile reacts with alcohols and hydrogen chloride with greater difficulty than do aliphatic nitriles to give the hydrochlorides of the imino esters of 1-adamantanecarboxylic acid, which are more stable than the corresponding compounds of the aliphatic series. 2. The hydrochloride of the methyl imino ester of 1-adamantanecarboxylic acid condenses with ethylenediamine, o-phenylenediamine and o-aminophenol in the usual manner to give the corresponding heterocyclic compounds. 3. The methyl imino ester of 1-adamantanecarboxylic acid when heated with ethanolamine gives the corresponding oxazoline. The hydrochloride of the methyl imino ester of 1-adamantanecarboxylic acid does not give the s-triazine when heated, and instead gives 1-adamantanecarbonitrile.