ZnO Nanoparticles: A Highly Effective and Readily Recyclable Catalyst for the One-Pot Synthesis of 1,8-dioxo-decahydroacridine and 1,8-dioxooctahydro-xanthene Derivatives

Abstract

ZnO nanoparticles as a worthwhile and recyclable catalyst have been used for the one-pot synthesis of 1,8-dioxo-decahydroacridines and 1,8-dioxooctahydro-xanthenes via multi-component reactions under solvent-free conditions. The presented method is mild, environmentally friendly, inexpensive and highly effective to give the products in good to excellent yields.

Fe3O4@Propylsilane@Histidine[HSO4‐] magnetic nanocatalysts: Synthesis, characterization and catalytic application for highly efficient synthesis of xanthene derivatives

“…After determination of optimum conditions, the performance of the HILMNPs as catalyst for the synthesis of other xanthene derivatives were evaluated by reaction of dimedone and aromatic aldehydes or isatin derivatives. In all studied cases, HILMNPs gave the corresponding products 3a–h and 5a‐e in better yields, and shorter times in comparison to previously reported (Table ).…”

“…Among them, 9‐arylxanthene‐1,8‐diones is found in many of the natural products and is used as multifunctional synthons due to the pyran ring . Various methods for the synthesis of 9‐arylxanthene‐1,8‐diones are described in the literature via condensation of aromatic aldehydes and 1,3‐cyclic diketone using various catalysts such as NaHSO 4 ·SiO 2 , TiO 2 /SO 4 2– , Dowex‐50 W, silica sulfuric acid, ZrOCl 2 ·8H 2 O, InCl 3 ·4H 2 O, CaCl 2 , Fe 3+ ‐montmorillonite, SmCl 3 , FeCl 3 ‐SiO 2 , Alumina‐sulfuric acid and amberlyst‐15 catalyst . Also, synthesis of spiro[indoline‐3,9′‐xanthene]trione derivatives in the presence of some catalyst such as p ‐TSA and SBA‐15‐Pr–SO 3 H was reported.…”

ZnO NPs: an efficient and reusable nanocatalyst for the synthesis of nitrones from DAG using H2O as a solvent at room-temperature

“…A strong band at 523 cm -1 is attributed to the Zn-O stretching band which is consistent with that reported before. These data are similar to the results observed by others [44]. The crystalline phases of the as-obtained compounds were determined by XRD.…”

“…Via this mechanism, the five-membered heterocyclic ring is formed. By deprotonation, the final products 5b are obtained [44].…”

Recent developments on nano-ZnO catalyzed synthesis of bioactive heterocycles

“…Recently, Safaei-Ghomi et al have synthesized a variety of structurally diverse xanthene derivatives using ZnO-nanoparticles as catalyst. In 2013, they developed a simple protocol for the efficient synthesis of 1,8-dioxooctahydroxanthene derivatives (53) via a one-pot pseudo three-component condensation between various aldehydes (5) and dimedone (16) in the presence of catalytic amount of ZnO-nanoparticles at 90 °C under solvent-free conditions [113] (Scheme 7). The optimized reaction conditions also worked satisfactorily in synthesizing a variety of N-aryl-1,8-dioxodecahydroacridine derivatives (54) in one-pot when the reaction was carried out in presence of aromatic amines (20) with excellent yield of 70-91% within just 5-25 min (Scheme 7).…”