Aryne-Mediated Arylation of Hantzsch Esters: Access to Highly Substituted Aryl-dihydropyridines, Aryl-tetrahydropyridines and Spiro[benzocyclobutene-1,1'-(3',4'-dihydropyridines)]
Aryne-Mediated Arylation of Hantzsch Esters: Access to Highly Substituted Aryl-dihydropyridines, Aryl-tetrahydropyridines and Spiro[benzocyclobutene-1,1'-(3',4'-dihydropyridines)]
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芳炔介导的 Hantzsch 酯的芳基化：获得高度取代的芳基-二氢吡啶、芳基-四氢吡啶和螺[苯并环丁烯-1,1-(3,4-二氢吡啶)]
DOI：
10.1055/s-0037-1611065
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Jones C
中科院分区：
文献类型：
--
作者：
Jones C
这是我们通过Hantzsch酯分子间芳烃反应生成高度官能化的2-芳基-1，2-二氢吡啶和2-methylene-3-aryl-1，2，3，4-tetrahydropyridines的研究的全部内容。此外，暴露在过量芳烃中发现了不寻常的3′-aryl-spiro[benzocyclobutene-1，1′-(3′，4′-dihydropyridines)].。机理上的见解是通过氚标记研究和密度泛函计算提供的，而初步的细胞毒性研究表明，螺旋环对卵巢癌细胞系中的结肠癌具有选择性，并且所有化合物对非癌细胞都具有高选择性指数。
This is a full account of our studies into the generation of highly functionalised 2-aryl-1,2-dihydropyridines and 2-methylene-3-aryl-1,2,3,4-tetrahydropyridines via intermolecular aryne ene reactions of Hantzsch esters. Furthermore, exposure to excess aryne revealed unusual 3′-aryl-spiro[benzocyclobutene-1,1′-(3′,4′-dihydropyridines)]. Mechanistic insights are provided by deuterium-labelling studies and DFT calculations, whilst preliminary cytotoxicity investigations reveal that the spirocycles are selective against colon carcinomas over ovarian cancer cell lines and that all the compounds have high selectivity indices with regards to non-cancer cells.