Abbaspour Tehrani, Kourosch

Herrebout, Wouter

Van Beek, Wim

Vande Velde, Christophe

Weemaes, Karel

Abstract: A one-pot, three-component, Cu(I)-catalyzed coupling of primary hydrazines, 5-chloropentan-2-one, and terminal alkynes was developed. The resulting 1-aza-6,7-dehydrotropanes compose a new class of substances while related 1-azatropanes are scarcely described in literature and closely resemble tropane alkaloids. Hydrogenation of the double bond in 1-aza-6,7-dehydrotropanes triggered a rearrangement, involving a [1,3]-hydride shift, forming cyclic hydrazones

Synthesis of 1-aza-6,7-dehydrotropanes via copper(I)-catalyzed coupling of 5-chloropentan-2-one with hydrazines and terminal alkynes

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