Iodine-catalyzed oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant in dimethyl carbonate

Csp2–O and C–C Bond Formation via Pd‐Catalyzed Coupling Reaction of 2,4‐Dichloroquinazoline

“…This compound was obtained as light‐yellow colored solid (ethanol); mp 217–219°C (Lit. mp 219–220°C); 127 mg, 60% yield; IR (KBr, cm −1 ) ν: 3325, 3116, 1609, 1337, 1280, 1106; 1 H NMR (400 MHz, CDCl 3 ): δ 11.43 (1H, s, NH), 8.95 (1H, d, J = 8.68 Hz), 7.99–7.90 (2H, m), 7.83 (1H, s), 7.69 (2H, d, J = 3.68 Hz), 6.72–6.70 (1H, m); 13 C NMR (100 MHz, CDCl 3 ); δ 157.8, 157.0, 153.8, 152.5, 147.0, 139.4, 134.9, 128.3, 128.2, 127.2, 119.5, 118.3, 114.2, 112.9; GC‐MS: 212.3 (M) + .…”

“…The most widely used method is probably with 2-aminobenzamide or their derivatives under acidic or basic conditions or in the presence of copper catalyst (Scheme 1) [50,51]. Recently, Fu and coauthors developed novel cascade methods starting from 2-halobenzoic acids or 2-halobenzamides [52][53][54][55][56].…”

Synthesis and antitumor activities of novel bis‐quinazolin‐4(3H)‐ones

“…Different representative synthetic methods including aza‐reaction, microwave‐assisted reaction, metal‐catalyzed reaction, ultrasound‐promoted reaction and phase‐transfer catalysis were reported for quinazoline compounds . A number of different strategies have been devised for condensation between aldehydes and o ‐aminobenzamides followed by oxidation of the aminal intermediate . Notably, most of the reported synthetic routes require excess amounts of oxidants or bases and suitable ligands or microwave irradiation conditions are necessary in some cases.…”

SeO2 Mediated Synthesis of Selected Heterocycles by Oxidative C−C Bond Cleavage of AcetophenoneDerivatives

“…Like the benzimidazole, there are various transformations reported for synthesis of quinazolinones by metal and metal free approach with condensation of anthranilamide with various simple aryl precursors. Various reports on this approach includes Zn,Pd,Ir or I 2 / DMSO‐catalyzed benzylic C−H amidation with benzyl alcohols, or condensation with benzyl halides or benzyl amine. Remarkably, an interesting Pd(OAc) 2 /BuPAd 2 /CO catalysedcarbonylative synthesis of quinazolinones was reported by Wu group .…”