Abstract
A simple and efficient protocol for the synthesis of highly substituted xanthenes is developed through the condensation of β-naphthol, aldehydes, and cyclic 5,5-dimethylcyclohexane-1,3-dione with zirconium oxychloride octahydrate as a catalyst via multicomponent condensation strategy. The present method gives good to excellent yields of substituted 9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one derivatives.
Highlights
Xanthenes and benzoxanthenes are biologically important drug intermediates
Santalin pigments have been isolated from a number of plant species [6]
In continuation of our efforts towards the development of novel methodologies under green chemical approaches we report a mild, efficient, and facile one-pot synthesis of multisubstituted xanthen derivatives for the first time by the multicomponent reaction of β-naphthol, benzaldehyde, and 5,5-dimethylcyclohexane-1,3-dione using zirconium oxychloride octahydrate as a Lewis acid catalyst (Scheme 1)
Summary
Xanthenes and benzoxanthenes are biologically important drug intermediates. They are cited as active oxygen heterocycles possessing antibacterial. Santalin pigments have been isolated from a number of plant species [6] Due to their useful spectroscopic properties, they are used as dyes [7], in laser technologies [8], and in fluorescent materials for visualization of biomolecules [9]. We investigated the condensation reaction of β-naphthol, benzaldehyde, and 5,5-dimethylcyclohexane-1,3dione using different Lewis acids catalysts and conditions such as La(OTf), ZnCl2, AlCl3, and Sr(OTf)3 [18]. Many of these reagents or catalysts are expensive, harmful, and difficult to handle especially on a large scale
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