シアノ基の特性を利用した含窒素複素環の効率的な構築法の開発と天然物合成への応用
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Viridicatin derivatives were synthesized from cyanoacetanilides utilizing the CN groups as electron-withdrawing groups and leaving groups. Also, the key scaffolds of glycocitlones were constructed via the intramolecular Houben-Hoesch-type reactions of cyanoacetanilides where the CN groups functioned as electrophiles. It was found that Houben-Hoesch-type reactions of cyanoacetanilides were promoted by α-functionalization such as perfluoroacylation and N,N-dimethylaminomethylenation and that introduction of such substituents at α-position with respect to the CN groups greatly influenced the physical properties and chemical reactivity of the CN groups.