Catalyst Free One-Pot Synthesis of Chromeno Quinolines and Their Antibacterial Activity

Abstract

An efficient greener one pot synthesis of dimethyl-dihydro-7H-chromeno[3, 2-h]quinolin-8(9H)-one derivatives has been synthesized through cyclization of aromatic aldehyde, dimidone and 8-hydroxy-quinoline through one-pot condensation method is described. The synthesized compounds are screened for further biological activities against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Bacillus using cut plate method and disc diffusion method.

NH4OAc‐Promoted Cascade Approach towards Aberrant Synthesis of Chromene‐Fused Quinolinones

“…Strikingly, chromene nucleus has displayed a center‐stage role in designing a number of fascinating fluorescent heterocyclic architectures of immense potential in medicinal and material chemistry . In particular, chromene‐fused quinolines constitute an integral part of several natural products including santiagonamine, and have been identified as antibacterial, and anticancer agents, sensors, dyes for mitocondrial imaging, estrogen receptor β ‐selective ligands, selective non‐steroidal progesterone receptor modulators, and glucocorticoid modulators (Figure ).…”

Recent Advances on Synthesis of Fused Chromeno‐Quinoline Heterocycles under Transition Metal‐Free Condition

“…One-pot, three component reaction methodology for the synthesis of quinoline fused chromene moieties from 8-hydroxy quinoline. [38] led to the formation of the target molecule chromeno [4,3b]quinolin-6-one (Scheme 5). Both electron donating and withdrawing substituent on the aldehydes produced good to excellent yields.…”

“…The reaction mechanism follows the Michael addition followed by cyclization. Sanasi et al also independently developed [38] a similar strategy for the synthesis of chromeno-quinolines under refluxing condition (Scheme 9). However, Sanasi et al took 8hydroxy quinoline and didn't employ any base.…”

“…Sanasi et alalso studied the anti-bacterial activity of the synthesized compounds against Pseudomonas aeruginosa,Bacillus subtilis, Escheria Colietc. [38] Two different series like benzo[f]chromeno [3,4-b]quinoline-6-one and chromeno [3,4-b]quinoline-6,11-dione scaffolds have been synthesized [39] Another multi component one-pot reaction methodology [40] for the synthesis of tetracyclic chromeno[2,3-b]quinoline-1-ol 20 was designed by Bhusare et al by using proline nitrate (19) as green organocatalyst (Scheme 11). The reaction occurred via condensation of four components-aromatic aldehydes, malononitrile, resorcinol and cyclohexanone.…”

Palladium/Copper Cocatalyzed C–H Activation and C–C Bond Regioselective Cleavage Reaction for the Synthesis of Fused Chromeno Quinolines

“…The fused chromeno quinolines have shown important roles in biological, medicinal, and fluorescence areas (Figure ). For example, chromeno quinolones A and B show significant anti-inflammatory and ulcerogenicscore activities. , The heterocyclic scaffold C , which is an emitting fluorophore, has excellent fluorescent properties . The synthesized dimethyl-dihydro-7 H -chromeno­[3,2- h ]­quinolin-8­(9 H )-one derivatives D show excellent antibacterial activity .…”