Abstract
In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1 : 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.
Highlights
Q UINAZOLINONES are widely used heterocyclic compounds of a great pharmaceutical interest
The aim of our work was to perform a synthesis of 3substituted quinazolinones using deep eutectic solvents
Deep eutectic solvents have found a great application in organic synthesis
Summary
Q UINAZOLINONES are widely used heterocyclic compounds of a great pharmaceutical interest Due to their structural diversity, they possess various biological activities, including antihelmintic,[1,2] antibacterial,[3,4,5] anti-inflammatory,[6] anticancer,[7,8] antihyperlipidemic[9] and antioxidant.[10] Their biological activities have been recognized by pharmaceutical industry and today many commonly available drugs contain different quinazolinones as an active ingredient (Figure 1). Hydrogen bond acceptors (HBAs; quaternary ammonium salts) are combined with hydrogen bond donors (HBDs; ureas, polyols, dicarboxylic acids) in different ratios, to obtain DES with desirable physical and chemical characteristics.[12,13]
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