Lewis acid promoted Friedländer condensation reactions between anthranilonitrile and ketones for the synthesis of tacrine and its analogues

Journal of the Brazilian Chemical Society

Jessé S. Da Costa¹  Diego S. Pisoni¹  Claudia B. Da Silva¹  Cesar L. Petzhold¹  Dennis Russowsky¹  Marco A. Ceschi¹ 

[1] ,Universidade Federal do Rio Grande do Sul Instituto de Química Porto Alegre RS ,Brazil

关键词: tacrine analogues;    Lewis acid;    Friedländer reaction;    Alzheimer's disease;   

DOI  :  10.1590/S0103-50532009000800009

来源: SciELO

【 摘 要 】

The scope of Lewis acid-promoted cyclodehydratation reactions between anthranilonitrile and several ketones, to afford tacrine and its derivatives, was expanded to include the use of various metal chloride salts not reported in the literature. The ability of the Lewis acids to effectively promote the cyclodehydratation between anthranilonitrile and cyclohexanone as the ketone was found to be the following order: InCl3 > AlCl3 ~ BF3.Et2O > FeCl3 > BiCl3 ~ SbCl3 ~ SnCl2.2H2O. The reactions were performed under both solvent and solvent-free conditions in good to excellent yields. Other Lewis acids screened, such as RuCl3, CeCl3, NiCl2, CoCl2.2H2O and CsCl were not effective.

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