Dihydroquinazolinones belong to an essential class of heterocyclic compounds which influence various cellular processes. They possess a wide range of biological proprietiesproperties.1 They are used for their antitumor, antidefibrillatory, antipyretic, antihypertonic, and diuretic activities and used also as antihistamine agonists, antidepressant, antibiotic, analgesic, and vasodilator agents.2
In addition, 2,3-dihydroquinazolinones have been exhibited important antiproliferative activity against several human cancer cell lines.3 They act analogously to the antimitotic agent colchicine 4 as efficient inhibitors of tubulin polymerization.5 Also, some 2,3-dihydroquinazolinone derivatives act as inhibitors theto the binding of colchicine to α,β-tubulin.6
Some examples of very significant quinazolinone molecules include medicinally approvedmedicinally-approved drugs like metolazone, quinethazone, raltitrexed, and fenquizone, as well as bio-active natural products such as febrifugine and isofebrifugine.7 A potential drug, ZD 9331, is under advanceadvanced clinical evaluation for treatment of solid tumors and other neoplasia, including colorectal tumors.8
Several methods are described in the literature for the preparation of these important classes of compounds. The synthesis of 2,3-dihydroquinazolin-4(1H)-ones has been achieved via condensation of anthranilamide, with aldehyde or ketone in presence of PTSA as catalyst under reflux conditions.9 The formation of quinazolinone has been also observed on refluxing anthranilamide with benzil in acetic acid, by using ZnCl2 as catalyst.10 Reductive cyclization of o-nitrobenzamides with aldehydes and ketones has been carried out to obtain the corresponding 2,3-dihydroquinazolin-4(1H)-ones in good yields.11 Various quinazolinone derivatives have been prepared from different anthranilic acid derivatives in a multi-step procedure ,12 or by the reaction of isatoic anhydride with Schiff’s bases.13
The synthesis of 2,3-dihydroquinazolinones was also achieved by reductive cyclisation of o-nitrobenzamide or o-azidobenzamide.14 Other recently reported methods involve isatoic anhydride, aldehydes and ammonium acetate or primary amine in the presence of different reagents or catalysts, namely PTSA,15 amberlyst-15 microwaved-assisted,16 montmorillonite K-10,17 ionic liquid,18 silica sulfuric acid,19 Zn(PFO)2,20 gallium (III) triflate ,21 and ceric ammonium nitrate.22