An expedient and straightforward solvent‐free synthesis of 1,8‐dioxo‐octahydroxanthenes using eco‐friendly aluminized polyborate catalyst

Abstract

The present work deals with a catalytic application of aluminized polyborate as a mild solid acid catalyst for multicomponent synthesis of 1,8-dioxooctahydroxanthenes under solvent-free condition at 100 C-110 C. It involves selective domino Knoevenagel-Michael reaction of 1 mole of aromatic aldehyde with 2 moles dimedone. The aluminized polyborate is simply synthesized by using boric acid and aluminum trichloride and characterized by FT-IR, XRD, SEM and EDAX techniques. The mild Lewis acidity, crystalline solid nature, stability and recyclability are significant features of the catalyst. The solvent-free condition, clean reaction profile, inexpensive and non-toxic catalyst, operational simplicity, good to excellent product yields, reduced reaction time and applicability to wide range of substrate are crucial features of this protocol.

Aluminized polyborate catalyzed efficient solvent-free synthesis of 1,8-dioxo-decahydroacridines via hantzsch condensation

“…In the present work, previously reported aluminized polyborate [8][9][10] was successfully employed for the one-pot synthesis of 1,8-dioxo-decahydroacridines by using substituted aromatic aldehydes (1 mmol), dimedone (2 mmol) and ammonium acetate (1.5 mmol) (Fig. 1).…”

“…7 The catalyst was characterized by FT-IR, XRD, SEM and EDAX techniques which are reported in our previous work on aluminized polyborate catalyst. [8][9][10]…”

“…7 The aluminized polyborate catalyst was used in our previous work for the solvent-free green synthesis of various heterocyclic molecules. [8][9][10] In literature several methodologies are been reported for the synthesis of acridinediones among them some are β-CD-mono-SO3H, 11 CdS thin film, 12 MNPs-N-propyl-benzoguanamine-SO3H, 13 AFGONs, 14 GO/CR-Fe3O4, 15 Iron-4 A molecular sieves, 16 MCM-41-Pr-THEIC, 17 Pd/AlO(OH), 18 urease, 19 Fe3O4@SiO2@Ni-Zn-Fe LDH, 20 nano-Fe3O4@SiO2-HBP-FeCl3, 21 citric acid, 22 TEMPO/CuCl2, 23 N-butyl pyridinium heptachlorodialuminate, 24 L-proline, 25 microwave irradiation, 26 Na + -MMT-[bip]-NH2 + HSO4 -, 27 MSrGONCs, 28 phosphate fertilizers, 29 ChCl:urea deep eutectic solvent, 30 Fe3O4@SiO2-Pr-Sulfurol-SO3H MNPs 31 and ultrasound-assisted 32 reaction.…”

The synthesis, structure, and catalytic properties of Cl‐substituted tridentate ONO Schiff base molybdenum(VI) complexes: Expeditious synthesis of 1,8‐dioxo‐octahydro‐xanthene derivatives

“…In recent years, more and more efficient and convenient methods of synthesis of oxanthanedione derivatives have been developed, such as the utilization of pyrazine dicationic Brönsted acidic ionic liquid, 6 choline peroxydisulfate ionic liquid, 7 ultrasound irradiation, 8 mesoporous Lewis acid polymer, 9 and aluminized polyborate catalyst under solvent‐free condition 10 . However, there are still some barriers challenging to overcome, such as expensive reagents, non‐satisfactory yields, and high catalyst loading.…”