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Construction of Tricyclic Nitrogen Heterocycles by a Gold(I)-Catalyzed Cascade Cyclization of Allenynes and Application to Polycyclic π-Electron Systems.

Hiroki KomatsuTakaya IkeuchiHitomi TsunoNorihito ArichiKosuke YasuiShinya OishiShinsuke InukiAiko FukazawaHiroaki Ohno
Published in: Angewandte Chemie (International ed. in English) (2021)
A novel approach to the direct construction of tricyclic nitrogen heterocycles based on gold-catalyzed cascade cyclization of aminoallenynes is described. The expected biscyclization reaction of hydroxyisobutyryl-protected aminoallenynes was efficiently promoted by a catalytic amount of BrettPhosAuNTf2 in the presence of iPrOH to produce 1,2-dihydrobenzo[cd]indole derivatives in good yields. When the reaction was combined with Friedel-Crafts acylation or palladium-catalyzed N-arylation, the resulting tricyclic products were efficiently converted into nitrogen-containing polycyclic aromatic compounds (N-PACs) with highly conjugated π-electron systems. A newly obtained hexacyclic indolium salt showed characteristic concentration-dependent absorption and emission properties.
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