ABSTRACT
A rapid, one-pot synthesis of eight benzo[a]furo[2,3-c]phenazine derivatives has been achieved in moderate to good yields in good yields via a multi-component of 2-hydroxynaphthalene-1,4-dione, arylglyoxal, indole (H, CH3) in the presence of H3PW12O40@Fe3O4-ZnO magnetic core-shell nanoparticles (MCNPs) under solvent-free conditions using microwave irradiation. The catalyst was synthesised and characterised by X-ray diffraction, EDX, TEM, FESEM, TGA, VSM and atomic force microscope. As an application for the synthesised nanocatalyst, degradation of methylene blue as heavy-mass organic pollution was measured. These results showed advantages for synthesis, such as mild reaction conditions, low energy consumption and economically affordable.
Subject(s)
Ferric Compounds/chemistry , Methylene Blue/isolation & purification , Microwaves , Phenazines/chemistry , Phenazines/chemical synthesis , Zinc Oxide/chemistry , Catalysis , Chemistry Techniques, Synthetic , Kinetics , Methylene Blue/chemistry , Nanoparticles/chemistryABSTRACT
BACKGROUND: A rapid, efficient, and environmentally benign procedure for the synthesis of novel furo [2,3-c]phenazine derivatives has been developed via reactions of 2-hydroxynaphthalene-1,4-dione, arylglyoxals, and indole in the presence of TiO2-SO3H-catalyst (TSAC) as a recyclable heterogeneous catalyst under solventfree conditions using microwave irradiation. INTRODUCTION: This study describes a successful approach for the synthesis of 2-(4-bromophenyl)-1-(1H-indol-3- yl) benzo[a]furo[2,3-c] phenazine in the presence of TiO2-SO3H-catalyst using microwave irradiation. OBJECTIVES: In this paper, we report an efficient and convenient method for the synthesis of phenazine derivatives from benzo[a]phenazin-5-ol, arylglyoxal derivatives, and indoles in the presence of TiO2-SO3H-catalyst under microwave irradiation. MATERIALS AND METHODS: All reagents and solvents were purchased from Merck and Aldrich and used without further purification. 1H NMR spectra (DMSO) were recorded on the Gemini-500 MHz spectrophotometer with TMS as an internal standard. RESULTS AND DISCUSSION: To investigate the reaction conditions for the synthesis of 2-(4-bromophenyl)-1-(1Hindol- 3-yl) benzo[a]furo [2, 3-c] phenazine derivatives, we performed a reaction between 2-hydroxynaphthalene- 1,4-dione (1 mmol) and aromatic 1,2-diamines (1 mmol) as a model. CONCLUSION: We demonstrated a green and straightforward procedure for the efficient synthesis of novel benzo[ a]furo[2, 3-c] phenazine derivatives in high yields via a one-pot, four-component domino protocol by using TiO2-SO3H as a mild, effective, non-toxic, and inexpensive solid acid catalyst without the addition of an organic co-solvent.
ABSTRACT
The importance of DHPs compounds and the need for examining the mechanism of their effect, mandated us to synthesize a number of carbon-14 labeled 1,4-dihydropyridine derivatives for pharmacological studies. Simple preparation and suitable radiochemical yield were advantages of this preparation.
ABSTRACT
A series of benzofuran-based N-benzylpyridinium derivatives 5a-o were designed and synthesized as novel AChE inhibitors. The synthetic pathway of the compounds involved the preparation of 4-(benzofuran-2-yl)pyridine intermediates via the reaction of different salicylaldehyde derivatives and 4-(bromomethyl)pyridine, followed by intramolecular cyclization. Subsequently, the 4-(benzofuran-2-yl)pyridines were N-benzylated by using appropriate benzyl bromide to afford the final product 5a-o. The results of in vitro AChE activity evaluation of synthesized compounds revealed that all compound had potent anti-AChE activity comparable or more potent than standard drug donepezil. The N-(3,5-dimethylbenzyl) derivative 5e with IC50 value of 4.1 nM was the most active compound, being 7-fold more potent than donepezil.