Catalytic Potential of Pyrazolone Based Dioxidomolybdenum(VI) Complexes for Multicomponent Biginelli Reactions, Epoxidation of Olefins and Oxidative Bromination of Phenol Derivatives

Three different types of dioxidomolybdenum(VI) complexes of 4‐acetyl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (Hmp, I )), 3‐methyl‐1‐phenyl‐4‐propionyl‐5‐pyrazolone (Hpp, II ), 4‐butyryl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (Hbutp, III ), and 4‐isobutyryl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (isobutp, IV ) have been isol...

Full description

Saved in:
Bibliographic Details
Published in:European journal of inorganic chemistry 2023-10, Vol.26 (28)
Main Authors: Maurya, Mannar R., Singh, Devesh, Bisht, Rahul, Avecilla, Fernando, Sharma, Akhilesh, Gupta, Puneet
Format: Article
Language:English
Subjects:
Alkenes
Benzaldehyde
Biomolecules
Bromination
Epoxidation
Hydrogen peroxide
Inorganic chemistry
NMR
Nuclear magnetic resonance
Phenols
Pyrazolones
Single crystals
Thermal analysis
Thiourea derivatives
Thymol
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Three different types of dioxidomolybdenum(VI) complexes of 4‐acetyl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (Hmp, I )), 3‐methyl‐1‐phenyl‐4‐propionyl‐5‐pyrazolone (Hpp, II ), 4‐butyryl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (Hbutp, III ), and 4‐isobutyryl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (isobutp, IV ) have been isolated and characterized by various spectroscopic (FT‐IR, UV/Vis, 1 H and 13 C NMR) techniques, thermal analysis and single crystal X‐ray analysis. These complexes adopt a distorted six‐coordinate octahedral geometry where ligands act as bidentate, coordinating through the two O atoms. These complexes have been used as catalysts to explore a single pot multicomponent (benzaldehyde or its derivatives, urea/thiourea and ethyl acetoacetate/phenyl acetoacatate) Biginelli reaction producing biologically active 3,4‐dihydropyrimidin‐2‐(1 H )‐one and 3,4‐dihydropyrimidin‐2‐(1 H )‐thione based biomolecules under solvent‐free conditions. Presence of H 2 O 2 improves the yield of dihydropyrimidin‐2‐(1 H )‐one but it acts as poison for the later molecule. Epoxidation of internal and terminal alkenes mainly resulted in the formation of the corresponding epoxide. The catalytic oxidative bromination of thymol, a reaction facilitated by vanadium dependent haloperoxidases, resulted in the formation of three product namely 2‐bromothymol, 4‐bromothymol and 2,4‐bromothymol. Other phenol derivatives have also been brominated effectively.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.202300302