Aryne-mediated arylation of Hantzsch esters: access to highly substituted aryl-dihydropyridines, aryl-tetrahydropyridines and spiro[benzocyclobutene-1,1’-(3’,4’-dihydropyridines)]

Weitao Sun, Piera Trinchera, Nada Kurdi, David Palomas, Rachel Crespo-Otero, Saeed Afshinjavid, Farideh Javid, Christopher R. Jones

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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.

Original languageEnglish
Pages (from-to)4591-4605
Number of pages15
Issue number23
Early online date25 Oct 2018
Publication statusPublished - 2018


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