Acetic Acid → HCID 20258679, Verbindung

Reaktionsgleichung

[F:1][CH:2]([C:8](=O)C1C=CC=CC=1)[C:3](OCC)=[O:4].[C:16]1([NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22].C(O)(=O)C>C(O)C>[F:1][C:2]1[C:3](=[O:4])[N:23]=[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]2=[N:22][CH:8]=1

Komponenten

Versuchsvorschrift

Refluxing of ethyl α-fluorobenzoylacetate (2.25 g, 10 mmol) with o-phenylenediamine (10 mmol) in the mixture of acetic acid and ethanol (25%) for 5 h gave 3-fluoro-1,5-benzodiazepin-2-one derivatives in good yields as follows. ##STR17## wherein X=H, 4-Me, 4-Cl or NO2. It is clear that the first step of this reaction is condensation of carbonyl ketone and amine by losing water and second step is cyclization of their ester with another amine by losing ethanol. When used p-CH3 or p-Cl o-phenylenediamine, these were condensed with α-fluorobenzoylacetate,