A novel method for the synthesis of tetrahydrobenzo[a]-xanthen-11-one derivatives using cerium(III) chloride as a highly efficient catalyst

Abstract

Cerium(III) chloride is found to be an highly efficient catalyst for the addition of aldehydes, b-naphthol and cyclic 1,3-dicarbonyl compounds/Meldrum's acid via a multicomponent reaction. The easy availability of starting materials, novel and eco-friendly procedure makes this strategy more useful for the preparation of tetrahydrobenzo[a]-xanthen-11one, and benzo[f]chromen-3-one derivatives.

Synthesis of tetrahydrobenzo[a]xanthen‐11‐ones using a high‐performance catalyst based on Fe3O4/MCM‐41/covalent organic polymer decorated with gold nanoparticles

“…Xanthenes can also be applied in the fabrication of laser dyes, 8 fluorescent sensors, 9 compounds for visualization of biomolecules, 10 as antagonists, 11 and photodynamic therapy 12 . Various acid catalysts have been employed for the fabrication of tetrahydrobenzo[a]xanthen‐11‐ones via the condensation of aromatic aldehydes, 1,3‐dicarbonyl compounds, and β‐naphthols 13–32 . The utility of these catalysts can be limited owing to difficulties in separation from the product, high cost, or low yields of the products.…”

“…Several approaches have been utilized for the fabrication of tetrahydrobenzo[a]xanthen‐11‐one derivatives 13–32 . However, these methods have restrictions of harsh reaction conditions, long reaction time, and often required expensive catalysts.…”

HAp‐encapsulated γ‐Fe2O3‐supported dual acidic heterogeneous catalyst for highly efficient one‐pot synthesis of benzoxanthenones and 3‐pyranylindoles

“…They can also be used as dyes, in laser technology and as pH‐sensitive fluorescent materials for visualization of biomolecules . Several procedures for the preparation of benzo[ a ]xanthene‐11‐one derivatives have been reported using various catalysts such as Zr(HSO 4 ) 4 , InCl 3 , TCCA, NaHSO 4 ⋅SiO 2 , XSA, HClO 4 –SiO 2 , PWA, nano‐TiO 2 , Ph 3 CCl, CeCl 3 ⋅7H 2 O, HY zeolite, Sr(OTf) 2 , RuCl 3 ⋅ n H 2 O and ruthenium anchored on multi‐walled carbon nanotubes …”

Introduction of a new bi-SO3H ionic liquid based on 2,2′-bipyridine as a novel catalyst for the synthesis of various xanthene derivatives

“…To improve these reactions several methodologies were reported in the literature. [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] Although these procedures provide an improvement, most of them suffer from disadvantages such as long reaction times, harsh reaction conditions, need to excess amounts of the reagent, use of organic solvents and use of toxic reagents. Additionally, only some of them are useful for the synthesis of all of the above mentioned xanthenes.…”