Synthesis and properties of the (n)(2,5)pyridinophane ring system.

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概要

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• The synthesis and properties of a series of [<I>n</I>](2,5)pyridinophane derivatives (<B>13a–e</B>) (<I>n</I>=10, 8, 7, and 6) are described. These compounds are prepared in low yields by the [Mo(CO)<SUB>6</SUB>]-induced cycloaddition reaction of 3-aryl-4,5-polymethylene-substituted isoxazoles (<B>11a–e</B>) with dimethyl acetylenedicarboxylate. The reaction pathways are suggested to involve the inclusion of the acetylenic ester across the C-4–C-5 bond of the N-complexed isoxazoles and the subsequent elimination of the oxygen atom from the resulting isoxazoline ring. The structures of <B>13a–e</B> are established on the basis of the <SUP>1</SUP>H-NMR, <SUP>13</SUP>C-NMR, and UV spectra. A significant strain for the pyridine ring in <B>13a–e</B> is reflected in the UV spectra. As the [<I>n</I>] decreases in <B>13–e</B>, there is a red shift in the absorption spectra. This feature is in good accordance with that observed in a series of [<I>n</I>]paracyclophane ring systems.

• 公益社団法人 日本化学会の論文

著者

• Nitta Makoto

  Department Of Applied Pharmacology Toyama Medical And Pharmaceutical University

• Kobayashi Tomoshige

  Department Of Chemistry Faculty Of Science Shinshu University

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