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

页码：2643 / 2647

页数：5

共 40 条

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