Symmetrical Bis-Hydrazone Ligand-Based Binuclear Oxido/Dioxido-Vanadium(IV/V) Complexes: Synthesis, Reactivity, and Catalytic Applications for the Synthesis of Biologically Potent 2-Phenylquinazolin-4-(3H)-ones
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Updated: Jun 1, 2025
Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Mannar R Maurya1, Monojit Nandi1, Sonu Kumar1
1Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, India.
Abstract:
Symmetrical bis(hydrazone)-based ligands, H4dar(bhz)2 (I), H4dar(fah)2 (II), H4dar(nah)2 (III), and H4dar(inh)2 (IV) obtained from 4,6-diacetylresorcinol (H2dar) and different hydrazides [benzoylhydrazide (Hbhz), isonicotinoylhydrazide (Hinh), nicotinoylhydrazide (Hnah), and 2-furoylhydrazide (Hfah)], were used to prepare potassium salts of binuclear cis-[VVO2]+ complexes, {K(H2O)2}2[(VVO2)2dar(bhz)2] (1), {K(H2O)2}2[(VVO2)2dar(fah)2] (2), {K(H2O)2}2[(VVO2)2dar(nah)2] (3), and {K(H2O)2}2[(VVO2)2dar(inh)2] (4), and binuclear [VIVO]2+ complexes, [{VIVO(MeOH)}2dar(bhz)2] (5), [{VIVO(MeOH)}2dar(fah)2] (6), [{VIVO(MeOH)}2dar(nah)2] (7), and [{VIVO(MeOH)}2dar(inh)2] (8). In the presence of warm MeOH/DMSO (4:1), 3 changed to {K(H2O)2}[(VVO2)2Hdar(nah)2]·DMSO (3a·DMSO). Single crystal XRD studies of 1 and 3a confirm a binuclear structure along with a distorted square pyramidal geometry of each vanadium center where bis{ONO(2-)} ligands coordinate through phenolate-O, azomethine-N, and enolate-O atoms of each unit. While growing crystals of 6 in EtOH, part of it oxidizes and gives [{VVO(OEt)}2dar(fah)2] (9) along with powdery 6. Complex 9 has a distorted octahedral structure. These complexes were used as catalysts for the synthesis of biologically important 2-phenylquinazolin-4-(3H)-ones having different aryl aldehydes, and they all show excellent catalytic performance (up to 97% yield) in less reaction time and low temperature, in the presence of 70% aqueous TBHP/30% aqueous H2O2 as a greener oxidant. Generally, these complexes perform better than their mononuclear analogues. Spectroscopy, DFT studies, and isolated intermediates have helped in proposing a suitable reaction mechanism for the catalytic reaction.
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