Thiamine hydrochloride (VB1) in aqueous media catalyzed the synthesis of polysubstituted quinolines via a one-pot strategy: a combined experimental and theoretical investigation
Mina Hajipour, Hossein Mehrabi, Hamid Reza Masoodi
TL;DR
This study shows how thiamine hydrochloride in water can efficiently synthesize complex quinoline compounds in one step, with high yields and catalyst reusability.
Contribution
A novel one-pot method using thiamine hydrochloride in water for synthesizing polysubstituted quinolines, supported by DFT calculations.
Findings
Thiamine hydrochloride catalyzed the synthesis of 4-amino-2-benzoylquinoline-3-carboxamide in water with high yields.
Solvent stability calculations showed water to be the most effective medium for the reaction.
Electronic properties of the compounds were estimated and correlated with solvent effects.
Abstract
In this work, an efficient one-pot three-component reaction of 2-cyano-N-methylacetamide, arylglyoxals, and arylamines in the presence of thiamine hydrochloride in H2O under reflux conditions was designed for the synthesis of 4-amino-2-benzoylquinoline-3-carboxamide. In this protocol, various synthetic methods such as Knoevenagel/Michael/cyclization cascade reactions were used to introduce different functional groups, such as amino and carboxamide groups, on the quinoline ring system in a single step. In addition to operational simplicity and absence of tedious separation procedures, this method offered the advantages of catalyst reusability and high product yields. Characterization techniques such as nuclear magnetic resonance spectroscopy, infrared spectroscopy, and CHN analysis were used to confirm the structure and purity of the synthesized compounds. In addition to the experimental…
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Taxonomy
TopicsChemical Synthesis and Analysis · Asymmetric Synthesis and Catalysis · Chemical Synthesis and Reactions