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首页> 外文期刊>RSC Advances >One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones
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One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones

机译：通过炔烃的碱催化异构化一步一步制备新型1-（N-吲哚基）-1,3-丁二烯，以获取5-（N-吲哚基）-萘醌

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A series of novel 1-( N -indolyl)-1,3-butadienes, as (1?:?1) mixtures of the ( E ) and ( Z ) dienes, was prepared in one step by base-catalysed isomerization of N -alkylindoles with a terminal butyne chain. The reaction conditions are mild, and in all cases the yields were very high (>90%). The ( E ) and ( Z ) dienes were separable by preparative TLC and could be fully characterized. This isomerization proceeded readily in the case of a butynyl chain, but didn't take place with a pentynyl chain. A mechanism was proposed for this reaction, based on previous studies on the isomerization of alkynes in basic media, and a key intermediate that supports the proposed mechanism could be isolated and fully characterized. A theoretical study of the proposed mechanism was performed by computational methods and the results validated the proposal. The reactivity of the synthesized dienes was studied in Diels–Alder reactions with p -benzoquinone, to obtain a small library of new 5-( N -indolyl)-1,4-naphthoquinones.The lack of reactivity in the case of the ( Z ) isomers was explained by calculation of the rotational curves of the central bond of the ( Z ) and ( E ) dienes. Finally, the cytotoxicity of the new 5-( N -indolyl)-1,4-naphthoquinones was tested against a panel of three cell lines.
机译：通过碱催化的N异构化一步制备一系列新的1-（N-吲哚基）-1,3-丁二烯，（E）和（Z）二烯的（1？：？1）混合物。 -带有末端丁炔链的烷基吲哚。反应条件温和，在所有情况下收率都很高（> 90％）。 （E）和（Z）二烯可通过制备TLC分离，并可以得到充分表征。在丁炔基链的情况下，这种异构化很容易进行，但在戊炔基链中却没有发生。基于先前在碱性介质中炔烃异构化的研究，提出了该反应的机理，并且可以分离和充分表征支持该机理的关键中间体。通过计算方法对提出的机制进行了理论研究，结果验证了该提议。在Diels–Alder与对苯醌的反应中研究了合成的二烯的反应性，以获得一个小的新的5-（N-吲哚基）-1,4-萘醌的文库。（Z情况下缺乏反应性异构体通过计算（Z）和（E）二烯的中心键的旋转曲线来解释。最后，针对一组三个细胞系测试了新的5-（N-吲哚基）-1,4-萘醌的细胞毒性。

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