Palladium and copper catalyzed cyclizations of hydrazine derived Ugi products: facile synthesis of substituted indazolones and hydroxytriazafluorendiones

Tetrahedron Letters(2012)

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Abstract
Indazolones are medicinally relevant targets. Herein we disclose an improved synthesis to N′-(acetamido-2-yl)-substituted indazolones with four points of diversity introduced by Ugi-[M]-amination and -amidation. The ring closure can be achieved by either conventional palladium catalysis or with a ligandless copper protocol. When α-unbranched isocyanides were employed the sole cyclization products of the copper catalyzed reactions are the hitherto undescribed 2-hydroxy-3H-3,4a,9a-triaza-fluorene-4,9-diones.
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Key words
Multicomponent reactions,Heterocycles,Palladium catalysis,Copper catalysis,Triazines,Indazolones,Ugi reaction,Hydroxytriazafluorendione
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