112425-22-6Relevant articles and documents
Synthesis and Reactions of 3-Amino-2-methyl-3H-[1,2,4]Triazolo[5,1-b]-quinazolin-9-one and 2-Hydrazino-3-phenylamino-3H-quinazolin-4-one
Saleh, Mohamed A.,Hafez, Yehia A.,Abdel-Hay, Foad E.,Gad, Wagdy I.
, p. 973 - 978 (2003)
The reaction of 3-N-(2-mercapto-4-oxo-4H-quinazolin-3-yl)acetamide (1) with hydrazine hydrate yielded 3-amino-2-methyl-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-one (2). The reaction of 2 with o-chlorobenzaldehyde and 2-hydroxy-naphthaldehyde gave the corresponding 3-arylidene amino derivatives 3 and 4, respectively. Condensation of 2 with 1-nitroso-2-naphthol afforded the corresponding 3-(2-hydroxy-naphthalen-1-yl-diazenyl)-2-methyl-3H-[1,2,4]triazolo[5,1-b] quinazolin-9-one (5), which on subsequent reduction by SnCl2 and HCl gave the hydrazino derivative 6. Reaction of 2 with phenyl isothiocyanate in refluxing ethanol yielded thiourea derivative 7. Ring closure of 7 subsequently cyclized on refluxing with phencyl bromide, oxalyl dichloride and chloroacetic acid afforded the corresponding thiazolidine derivatives 8, 9 and 10, respectively. Reaction of 2-mercapto-3-phenylamino-3H-quinazolin-4-one (11) with hydrazine hydrate afforded 2-hydrazino-3-phenylamino-3H-quinazolin-4-one (12). The reactivity 12 towards carbon disulphide, acetyl acetone and ethyl acetoacetate gave 13, 14 and 15, respectively. Condensation of 12 with isatin afforded 2-[N-(2-oxo-1,2-dihydroindol-3-ylidene)hydrazino] -3-phenylamino-3H-quinazolin-4-one (16). 2-(4-Oxo-3-phenylamino-3,4-dihydroquinazolin-2-ylamino)isoindole-1,3-dione (17) was synthesized by the reaction of 12 with phthalic anhydride. All isolated products were confirmed by their ir, 1H nmr, 13C nmr and mass spectra.
