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

被引：36

作者：

Gomes, Rafael F. A. ^{[1
]}

Coelho, Jaime A. S. ^{[1
]}

Frade, Raquel F. M. ^{[1
]}

Trindade, Alexandre F. ^{[1
]}

Afonso, Carlos A. M. ^{[1
]}

机构：

[1] Univ Lisbon, Fac Pharm, Inst Invest Medicamento iMed ULisboa, P-1649003 Lisbon, Portugal

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 20期

关键词：

SOLVENT-FREE CONDITIONS; HIGH-PRESSURE REACTION; REACTION VOLUMES; IMINIUM SALTS; ACTIVATION; TRIARYLMETHANES; CHEMISTRY; RING; EPOXIDES; PLATFORM;

D O I：

10.1021/acs.joc.5b01875

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 mu M.

引用

页码：10404 / 10411

页数：8

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