Solvent-free synthesis of xanthene derivatives by Preyssler type heteropolyacid (original) (raw)
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Journal of the Iranian Chemical Society, 2012
A simple, efficient, and environmentally benign route was developed for the preparation of 14-aryl or alkyl-14H-dibenzo[a,j]xanthene, 1,8-dioxo-octahydroxanthene and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones from condensation of various aldehydes with (i) b-naphthol, (ii) cyclic 1,3-dicarbonyl compounds and (iii) b-naphthol and cyclic 1,3-dicarbonyl compounds, using novel polymeric catalyst [poly(AMPS-co-AA)] under solvent-free conditions. Use of easily available catalyst, shorter reaction times, better yields, simplicity of the reaction, heterogeneous system, and easy work-up are the advantages of the present method.
DABCO promoted multi-component one-pot synthesis of xanthene derivatives
Research Journal of Chemical Sciences …, 2012
The reaction of dimedone with various heteroaryl aldehydes afforded the corresponding heteroaryl substituted xanthene derivatives. Reaction proceeds via initial Knoevenagel, subsequent micheal and final heterocyclization reactions using 1,4diazabicyclo(2.2.2)octane (DABCO) as catalyst. Short reaction time, environmentally friendly procedure, no need to use cumbersome apparatus for the purification of the products and excellent yields are the main advantages of this procedure which makes it more economic than the other conventional methods.
DABCO Catalyzed Synthesis of Xanthene Derivatives in Aqueous Media
2013
The reaction of 5,5-dimethylcyclohexane-1,3-dione with various heteroarylaldehydes afforded the corresponding heteroaryl substituted xanthene derivatives 1(a-f). The reaction proceeds via the initial Knoevenagel, subsequent Michael, and final heterocyclization reactions using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a catalyst in aqueous media. The synthesized heteroaryl substituted xanthenes 1(a-f) reacted with malononitrile to obtain different alkylidenes 2(a-f). Short reaction time, environmentally friendly procedure, avoiding of cumbersome apparatus, and excellent yields are the main advantages of this procedure which makes it more economic than the other conventional methods.
[DBN][HSO4]-Promoted Facile and Green Synthesis of Xanthene Derivatives via Knoevenagel Condensation
Der Pharmacia Lettre, 2021
A novel [DBN] [HSO 4 ] difunctionalized bronsted acidic ionic liquid-promoted Knoevenagel condensation followed by cyclization protocol has been developed for the first time by a successive reaction of aldehydes, and dimedone to afford xanthene derivatives in high to excellent yields at 80 ο C temperature. The ionic liquid provided the capability to allow a variability of functional groups, short reaction times, easy workup, high yields, recyclability of the catalyst and solvent-free conditions, thus providing economic and environmental advantages.
Synthesis, spectroscopic and photophysical studies of xanthene derivatives
Journal of Molecular Structure, 2017
We report on the experimental, crystal structure and computational investigation of a new class of xanthenes obtained by the reaction of salicylaldehyde and its derivatives with, 5,5-Dimethylcyclohexane-1,3-dione (Dimedone). The synthesized xanthenes were characterized by state-of-the-art techniques, such as IR, Raman, 1 H and 13 C NMR, Single Crystal X-ray crystallography, UV-Vis and photophysical measurements. The structure, groundandexcited-state properties of one xanthene derivative was investigated using Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) calculations with and without solvent (ethanol). The optimized geometries and predicted IR frequencies were in good agreement with experimental data. Hirshfeld surface analyses were carried out to gain insight on the close-contact interactions of the crystal, where hydrogen showed the highest contribution (66.1%). The synthetic route proposed in this work does not use any catalysts and leads to high yields (75-85 %), therefore being an interesting alternative to synthesize xanthene derivatives.
Applied Catalysis A: General, 2007
This article was originally published in a journal published by Elsevier, and the attached copy is provided by Elsevier for the author's benefit and for the benefit of the author's institution, for non-commercial research and educational use including without limitation use in instruction at your institution, sending it to specific colleagues that you know, and providing a copy to your institution's administrator. All other uses, reproduction and distribution, including without limitation commercial reprints, selling or licensing copies or access, or posting on open internet sites, your personal or institution's website or repository, are prohibited. For exceptions, permission may be sought for such use through Elsevier's permissions site at: http://www.elsevier.com/locate/permissionusematerial A u t h o r ' s p e r s o n a l c o p y Short communication Dowex-50W promoted synthesis of 14-aryl-14H-dibenzo[a,j]xanthene and 1,8-dioxo-octahydroxanthene derivatives under solvent-free conditions