Green synthesis of biologically and industrially important heterocyclic derivatives

Abstract

Aromatic/hetero aromatic carbaldehyde based heterocyclic derivatives were synthesized through an eco-friendly greener approach, by reaction of aromatic/hetero aromatic carbaldehyde hydroxynaphthalene-1-carbaldehyde,3-formylchromone, bromophenyl)-ferrocene-prop-2-en-1-one, etc.) with (2- 1-(4- different aromatic/hetero aromatic active methylene compounds (different barbituric acid derivatives, meldrum's acid, dimedone, azomethine ylides etc,) in presence of recyclable and reusable green catalysts. The use of solvent-free heating/room temperature reaction in presence of green catalysts for the synthesis of heterocyclic derivatives makes the present protocol as green and eco-friendly. A comparative study of conventional method and solvent-free method highlights the advantages, such as admirable yield, reduced reaction time with eviction of environmentally hazardous solvents, which leads to sustainability. The chemical structures of compounds were characterized by spectral techniques like IR, 1H NMR, 13C NMR and mass spectrometry and employed analytical techniques to characterize the newly developed catalytic systems. Additionally, computational studies of synthesized compounds were performed using density functional theory (DFT) at M06 level and 6-311G (d,p) basis set to elucidate the electronic structures, and counter check the experimental findings. Overall, DFT findings at M06/6-311G (d,p) level show good agreement with the experimental data which confirms the purity of entitled compounds. Natural bond orbital (NBO) analysis and non-linear optical (NLO) properties were explored at the M06-/6-311G (d,p) level of theory. NBO analysis confirms that hyper conjugative interactions are responsible for the stability of compounds. Furthermore, the global reactivity parameters were calculated using the FMOs energies which indicate that most of the compounds possess more donating capability and stability. NLO findings confirmed that newly synthesised compounds have superior properties as compared to prototype standard compounds which unveiled their potential applications for optoelectronic technology. Some of the compounds were examined for single crystal X-ray diffraction study, which is additionally validated with Hirshfeld surface analysis. The molecular docking study, it was clear that the examined compounds can produce different kinds of non-covalent interactions within the hydrophobic cavity complexes and restrict the functioning of bacterial DNA, thereby satisfying the crucial feature of a molecule to behave like an antimicrobial agent and it was proved by invitro screening. The evaluation of pharmacological activities of newly synthesized heterocyclic derivatives, including antibacterial and antifungal properties, through insilico and invitro studies also shows comparable results and highlighted their potential application in biomedical fields.