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

Tijdschriftbijdrage - Tijdschriftartikel

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.
Tijdschrift: Synlett : accounts and rapid communications in synthetic organic chemistry
ISSN: 0936-5214
Volume: 29
Pagina's: 2643 - 2647
Jaar van publicatie:2018
Trefwoorden:A1 Journal article
BOF-publication weight:1
CSS-citation score:1
Authors from:Higher Education