Über die Reaktion von freier Anthranilsäure mit freien Imidsäureestern

Abstract

Freie Anthranilsaurc reagiert mit freien Imidslureestern zu Derivaten des 4-Hydroxy-chinazolins. Es wird die Darstcllung von 4-Hydroxy-chinazolyl-(2)carbonsaurenitrilen, der daraus herzustellenden Carbonsauren und von 2.2'- Polymethylcn-bis-[4-hydroxy-chinazolinen] beschrieben.Wahrend sich aliphatische a-Aminosiuren mit freien Imidstiureestem zu Amidinosauren umsetzen und hierbei nur in wenigen Fallen die Bildung von Imidazolonen beobachtet wirdz),

Biological Activity of Quinazolinones

“…In 1960, Ried et al reported [25][26][27] the reaction of imidates and 2-aminobenzoic acid in methanol at 80°C to afford the desired quinazolinones (7) in good yields (Figure 2).…”

“…In 2006, (−)-chaetominine 24, a tetracyclic tripeptide alkaloid ( Figure 7) was isolated from an endophytic fungus, Chaetomium sp. IFB-E015, and showed smaller IC 50 than the most frequently prescribed anticancer drug 5-fluorouracil Quinazolinone alkaloids, auranomides A-C (25)(26)(27) were isolated from Penicillium aurantiogriseum and showed moderate cytotoxicity against human tumor cells [50]. Sartorymensin (28), a hexcyclic indoloazepine-fused quinazolinone derivative was isolated from Neosartorya siamensis fungus (KUFC 6349) showed a moderate in vitro growth inhibitory activity of several cancer cell lines [51].…”

Mo (CO)6‐assisted Pd‐supported magnetic graphene oxide‐catalyzed carbonylation‐cyclization as an efficient way for the synthesis of 4(3H)‐quinazolinones

“…Palladium‐catalyzed oxidative insertion reaction of isocyanide with anthranilamide, carboxylic acids and amines, the carboxylation of ortho C–H bonds in anilides leading to N ‐acyl anthranilic acids and then treatment with anilines in the presence of PCl 3 , and the reaction of nitriles with lithiated anthranilamides are reported for the preparation of this class or compounds. In addition, other methods including microwave‐assisted condensation of anthranilic acids, oxidative reaction between benzyl halides, isatoic anhydride and primary amines, and the condensation of imidates with anthranilic acids, are reported for this purpose. Amine‐induced thermal rearrangement of iminobenzoxazines, phosphine‐catalyzed intramolecular aza‐Wittig reaction, copper iodide‐catalyzed reaction between anthranilamide, and terminal alkynes and azides have also been used for the synthesis of 4(3 H )‐quinazolinone.…”

Indium(III) Trifluoromethanesulfonate: a Reusable Catalyst for the Sol-vent-free Synthesis of some Quinazolinones/thiones

“…6 The most general method for the preparation of octahydroquinazolinones/thiones involves the one-pot Biginelli condensation reaction of cyclic 1,3-dione, aromatic aldehydes and urea/thiourea in the presence of a Lewis or mineral acids. Although, synthesis of octahydroquinazolinones/thiones via the Biginelli reaction using several reagents have been previously reported, [7][8][9][10][11][12][13][14] some of the procedures have disadvantages such as, long reaction time, use of strongly acidic condition or organic solvents, unsatisfactory product yield, and also side products. Due to its low toxicity, ease of han- dling, and high activity, the In(III) triflate has emerged as a useful catalyst in many organic synthesis, including, highly chemo and regioselective head-to-tail heterodimerization of vinylarenes, 15 chemoselective conversion of aldehydes to acylals, 16 synthesis of 2,4-disubstituted quinolines, 17 reaction of sugars, 18 and Friedel-Crafts sulfonylation of arenas.…”