Amidobenziodoxoles 2 can be prepared from benziodoxole 1, trimethylsilyltriflate and the appropriate amides in the form of stable, microcrystalline compounds. Amidobenziodoxoles 2 react with adamantane 3 or N,N-dimethylarylamines 5 to afford the corresponding products of amidation, 4 and 6.
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In conclusion, we have prepared and isolated as individual, stable compounds amidobenziodoxoles 2a- e. Compounds 2 are potentially useful reagents for direct amidation of adamantane and N,N- dialkylarylamines. Acknowledgement. This work was supported by a research grant from the National Science Foundation (NSF/CHE-9505868) and by the Undergraduate Research Opportunities Program at the University of Minnesota.