Synthesis of new 4(3H)-quinazolinone derivatives under solvent-free conditions using PEG-400

Abstract

Anthranilic acid 1 was reacted with chloroacetyl chloride in dichloromethane containing triethylamine to yield 2-chloromethyl benzo [d] [1,3]oxazin-4-one 2, which on treatment with aromatic amines yielded 2-(chloromethyl)-3-arylquinazolin-4(3H)-one 3. The latter on reaction with nitrogen nucleophiles such as ethyl piperidine-4-carboxylate, morpholine and piperidine-4-one in CH 3 CN containing K 2 CO 3 and catalytic amount of KI under refluxing conditions, gave 1-(4-oxo-3-aryl-3,4-dihydroquinazolin-2-ylmethyl)piperidine-4-carboxylic acid ethyl ester (4), 2-morpholine-4-ylmethyl-3-aryl-3H-quinazolin-4-one (5), 2-(4-oxopiperidine-1-ylmethyl)-3-aryl-3H-quinazolin-4-one (6) respectively. All the above reactions have been carried out under solvent-free conditions in the presence of PEG-400 by simple physical grinding in a mortar and pestle. The structures of all the new products obtained in the present work are supported by spectral and analytical data (IR, 1 H NMR and Mass spectroscopy).

A Review on Methods of Synthesis of Quinazolines and (4H)-3,1-Quinazolin-4-ones

“…Scheme 13. Synthesis of 2,3-disubstituted quinazolin-4(3H)-ones using amides Anthranilic acid on reaction with acid chloride also forms benzoxazinone which on reaction with primary amine yield 2,3disubstituted-quinazolin-4(3H)ones (Acharyulu et al, 2008, Ameta et al, 2006)(Scheme 14). Acetanthranil (3,1,4benzoxazinone) can be easily prepared by heating anthranilic acid or a substituted anthranilic acid with an acid anhydride.…”

Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents

“…Quinolines are very important compounds used for new drug development. They are reported as highly selective cytotoxic ( Luo et al, 2009 ; Bawa et al, 2010 ; Meshram et al, 2012 ; Sidoryk et al, 2015 ), broad-spectrum antimicrobial (including activity against Mycobacterium tuberculosis as well as HIV-1 integrase inhibition activity) ( Wang et al, 2019 ), antileishmanial ( Asif, 2014 ), anticonvulsant, anti-inflammatory, cardiovascular activity ( Acharyulu et al, 2008 ; Kumar, Bawa, and Gupta, 2010 ), and have antidiabetic effect ( Shang, et al, 2018a ).…”

Green chemistry approach to the synthesis of 3-substituted-quinazolin-4(3H)-ones and 2-methyl-3-substituted-quinazolin-4(3H)-ones and biological evaluation

“…Therefore, green synthetic methods are favorable in this manner. So far, some green techniques have been applied for their synthesis, like microwaves (19)(20)(21), ultrasound (22)(23)(24), grinding methods (25,26) or ionic liquids (11,24,27). As one of the green synthetic methods, utilization of deep eutectic solvents in the synthesis of different heterocycles is getting more attention in the last few years, but only few papers describe their application in quinazolinone synthesis.…”