Aryne-Mediated Arylation of Hantzsch Esters: Access to Highly Substituted Aryl-dihydropyridines, Aryl-tetrahydropyridines and Spiro[benzocyclobutene-1,1′-(3′,4′-dihydropyridines)]

Autor:	Christopher R. Jones, S. Afshinjavid, David Palomas, Weitao Sun, Farideh A. Javid, Piera Trinchera, Rachel Crespo-Otero, Nada Kurdi
Rok vydání:	2018
Předmět:	010405 organic chemistry Aryl Organic Chemistry High selectivity 010402 general chemistry 01 natural sciences Combinatorial chemistry Aryne Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Benzocyclobutene Cytotoxicity Ene reaction
Zdroj:	Synthesis. 50:4591-4605
ISSN:	1437-210X 0039-7881
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7fa719db7dce96aad2659e2d931e7641 https://doi.org/10.1055/s-0037-1611065 Zobrazit plný text záznamu