Most secondary amides, such as benzanilide and acetanilide, favor the trans form, but N-methylation of these compounds change the conformation from trans to cis form. On the basis of this property, we have developed pH-induced conformational alteration systems bearing pyridinecarboxamide moieties. Recently, we designed macrocyclic pyridinecarboxamide oligomers which showed cis-favored unique feature and conformational alteration at acidic condition. However, there is no definitive synthetic routes to these compounds. In this study, we developed efficient synthetic method of the macrocyclic N-alkyl aromatic oligoamides bearing pyridinecarboxamides. The pyridinecarboxamide oligomer chains were prepared from acyl chloride or by C–N cross-coupling reactions. To obtain macrocyclic oligoamides, cyclization reactions of these oligomers were investigated in a similar synthetic manner. Furthermore, we will report the conformational preference of these compounds and their constituent units.

Efficient synthesis and conformational analysis of N-alkyl aromatic oligoamides bearing pyridinecarboxamides

256th National Meeting (2018)

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