Polycyclic N-heterocyclic compounds. Part 60: reactions of 3-(2-cyanophenyl)quinazolin-4(3H)-ones with primary amines.
The reaction of 3-(2-cyanophenyl)quinazolin-4(3H)-one with various primary alkylamines gave 3-alkylquinazolin-4(3H)-ones via an addition of the nucleophile, ring opening, and ring closure (ANRORC) mechanism. This type of reaction required hydroxy group functionality in either the solvent or reagent. When hydroxylamine was used as nitrogen nucleophile, the intermediate of this reaction was isolated and found to be an amide oxime. When ethylenediamine was used as the nucleophile, the amidine moiety of the intermediate decomposed to give a benzanilide.
Okuda
Kensuke
K
Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan. okuda@gifu-pu.ac.jp
Tagata
Tsuyoshi
T
Kashino
Setsuo
S
Hirota
Takashi
T
Sasaki
Kenji
K
D000588:Amines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D052999:Quinazolinones / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D006571:Heterocyclic Compounds; D011083:Polycyclic Compounds; D052999:Quinazolinones