Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties

Abstract

Rapid and facileaccess to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties.

The applications of β‐keto amides for heterocycle synthesis

“…Besides, Lee and co-workers used ferromagnetic Fe 3 O 4 nanoparticles as a recyclable catalyst for this synthesis [158]. Using 1 equiv of Et 3 N as the base and PEG-300 as the recyclable solvent, β-keto amides 346 reacted quickly with 4-chloro-3-formylcoumarine 347 to afford a series of novel chromeno [4,3]pyridine-2,5-diones 348 with high yield and substrate scope (Scheme 84) [159]. These heterocyclic compounds exhibited potential antimicrobial activities and antioxidant properties.…”

Synthesis and anticancer activity evaluation of some new derivatives of 2-(4-benzoyl-1-piperazinyl)-quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline.

“…The N-phenylacetoacetamide 5 was synthesized according to the procedure reported in the literature (12). The 4-methylquinolin-2(1H)-one 6 was also synthesized according to the procedure reported elsewhere (13).…”

One‐pot three‐component synthesis of novel chromeno[3,2‐c]pyridine‐1,9(2H)‐diones by using SnCl2⋅2H2O as catalyst

“…Several methods have been yet used for the synthesis of chromenopyridine derivatives with different substrate via the hetero‐Diels‐Alder reaction, intramolecular CC bond coupling reactions, [3 + 2 + 1] cycloaddition strategy and etc. [25] including two or multicomponent reaction such as under catalyst and solvent free conditions [26], under reflux conditions in the presence of piperidine [27] or niobium pentachloride [28] or PEG‐300 [29] and magnesium oxide [30] via microwave irradiation [31], solvent‐free conditions [32], and in particular, there are two reports of synthesis of somewhat similar compounds, one in ionic liquid in the presence of toluene sulfonic acid in a three‐component reaction [33], and the other in a multi‐step synthesis [34].…”