Aromatic amide compounds, such as acetanilide and benzanilide, predominantly exist as trans form in crystal and solution. However, N-methylation of aromatic amide compounds induces conformational alternation; cis form became the predominant form in solution and crystal. These conformational alternation is very important in drug design since the N-alkylation of amide compounds would easily change the shape of the molecule, resulted in the loss of activity. In this study, we synthesized and examined the crystal structure of N-vinyl and alkynyl acetanilide derivatives. In addition, we find the effective method to cleave these alkene and alkyne moiety, which would be useful as the linkage of functional molecules with amide main chain via nitrogen atom.

Conformational properties of N-vinyl and alkynyl substituted aromatic amides compounds

255th National Meeting (2018)

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