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

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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
Synlett ( IF 1.7 ) Pub Date : 2018-10-24 , DOI: 10.1055/s-0037-1611041
Kourosch Tehrani ₁ , Wim Van Beek ₁ , Karel Weemaes ₁ , Wouter Herrebout ₂ , Christophe Vande Velde ₃

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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.

中文翻译：

通过铜 (I)-催化偶联 5-Chloropentan-2-one 与肼和末端炔烃合成 1-Aza-6,7-dehydrotropanes

开发了一种一锅、三组分、Cu(I) 催化的伯肼、5-氯戊烷-2-one 和末端炔烃的偶联。由此产生的 1-aza-6,7-dehydrotropanes 构成了一类新的物质，而相关的 1-azatropanes 在文献中几乎没有描述，并且与托烷生物碱非常相似。1-aza-6,7-dehydrotropanes 中双键的氢化引发重排，涉及 [1,3]-氢化物移位，形成环腙。

更新日期：2018-10-24

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