Synthesis of Symmetric Bis(N-alkylaniline)triarylmethanes via Friedel–Crafts-Catalyzed Reaction between Secondary Anilines and Aldehydes

Autor:	Rafael F. A. Gomes, Jaime A. S. Coelho, Raquel F. M. Frade, Alexandre F. Trindade, Carlos A. M. Afonso
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Aryl Organic Chemistry Substrate (chemistry) Iminium Aldehyde Medicinal chemistry Catalysis chemistry.chemical_compound chemistry High pressure Electrophile Organic chemistry Friedel–Crafts reaction
Zdroj:	The Journal of Organic Chemistry. 80:10404-10411
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.5b01875
Popis:	The first general protocol for the preparation of symmetric triarylmethanes bearing secondary anilines by ytterbium-catalyzed Friedel-Crafts reaction of hetero(aryl) aldehydes and secondary anilines is reported. Mechanistic studies indicated that the iminium ion intermediate is the electrophilic partner. The reaction is greatly accelerated by high pressure (9 kbar) and showed a broad substrate scope on the hetero(aryl) aldehyde. The new triarylmethanes exhibited activity against HT-29 cancer cell lines, with the best result scoring an IC50 of 1.74 μM.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0791e86140b167f3e8cfb9263ad7c9f1 https://doi.org/10.1021/acs.joc.5b01875 Zobrazit plný text záznamu