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Synthesis 1997; 1997(9): 1034-1040
DOI: 10.1055/s-1997-1304
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Adamantylation and Adamantylalkylation of Amides, Nitriles and Ureas in Trifluoroacetic Acid

Elvira Shokova
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Publication Date:
31 December 2000 (online)

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A new preparative method for N-adamantylation of carboxylic acid amides, ureas and for C5-adamantylation of barbituric acid in trifluoroacetic acid (TFA) is proposed. Tertiary 1-adamantanols and 1-(1-adamantyl)alkanols were used as adamantylating agents. The reaction of 1-(1-adamantyl)alkanols with nitriles in TFA solution was employed for the first time for the preparation of N-[1-(1-adamantyl)alkyl]amides.

N-[3-(R)-1-adamantyl]- and N-(1-adamantylalkyl)amides