Studies on 4(1H)-quinazolinones. III. Some derivatizations of 2-ethoxycarbonylalkyl-1-substituted-4(1H)-quinazolinones.

Green Synthesis of Substituted Anilines and Quinazolines from Isatoic Anhydride-8-amide

“…13 C NMR (101 MHz, DMSO- d 6 ): δ 173.65, 171.96, 149.57, 133.27, 129.47, 114.76, 114.37, 111.40, 38.34, 34.03. MS (m/z): 207 (M − 1), 209 (M + 1) 22 .…”

“…Our synthetic method simplifies isatin transformations considerably compared to prior methods. Synthesis of isatoic anhydride from isatin previously required using reagents such as peroxides 21,22 , phenyliodide 23 , and NBS 24 ; making benzamide derivatives from isatin required using chromic acid 25 , peroxide/phosphate buffer systems 26 , or in situ generated hydrazoic acid 27,14 ; and generating amino benzamide derivatives from isatoic anhydride required using ammonia 22,28 and ammonium carbonate 29 . In contrast, we can now approach multiple classes of derivatives from IAA using mild, established reactions.…”

Solvent-free synthesis of 5-(aryl/alkyl)amino-1,2,4-triazines and α-arylamino-2,2′-bipyridines with greener prospects

“…It should be noted that a very few examples have been reported for the substitution of cyano-group by reaction of amines under solvent-free conditions in some other heterocycles, for instance, in pyrazines, 46 4H-imidazole, 47 1-arylethene-1,2,2-tricarbonitriles, 48 quinazolinone (in an aqueous media), 49 and benzonitrile. 50 In addition, the intermolecular cyclization reaction of tetrazine followed by the ipso-substitution of cyanogroup has been reported.…”

Pyrrolo[1,2-a]quinazolines: synthesis and biological properties

“…The pyrrolo[1,2-a]-quinazoline derivatives 9 were observed in mixtures with the pyrroles only in the case when dimethyl acetylenedicarboxylate was used as dipolarophile (R = E = COOMe) and were isolated in two cases with moderate yields. [13][14][15][16][17][18][19][20] By intramolecular cyclisation of the 1,2-dihydroquinazolinepropionitrile 3-oxides in alkaline media (Scheme 4) the corresponding 1-iminotetrahydropyrrolo[1,2-a]quinazoline-4-oxides 10 were obtained. …”