Synthesis of 1-Aza-6,7-dehydrotropanes via Copper(I)-Catalyzed Coupling of 5-Chloropentan-2-one with Hydrazines and Terminal Alkynes

被引：1
|
作者：
Van Beek, Wim E. [1 ]
Weemaes, Karel [1 ]
Herrebout, Wouter A. [2 ]
Vande Velde, Christophe M. L. [3 ]
Tehrani, Kourosch Abbaspour [1 ]
机构：
[1] Univ Antwerp, Dept Chem, Organ Synth, Groenenborgerlaan 171, B-2020 Antwerp, Belgium
[2] Univ Antwerp, Dept Chem, Res Grp Mol Spect, Groenenborgerlaan 171, B-2020 Antwerp, Belgium
[3] Univ Antwerp, Fac Appl Engn, Adv Reactor Technol, Groenenborgerlaan 171, B-2020 Antwerp, Belgium
来源：
SYNLETT | 2018年 / 29卷 / 20期
关键词：
multicomponent reactions; alkynes; hydrazines; ketones; copper catalysis; 1-azatropanes; AZOMETHINE IMINES; 1,3-DIPOLAR CYCLOADDITION; HETEROCYCLES; ALDEHYDES; CATALYST; AMINES;
D O I：
10.1055/s-0037-1611041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：2643 / 2647
页数：5
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