Synthesis of 3,4-dihydro- and 1,4-dihydro-5H-1,3,4-benzotriazepin-5-ones

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

“…In the course of our investigations on these compounds, we studied the reaction of hydrazide with carbonyl compounds in an attempt to prepare novel derivatives of isoxazole heterocyclic system. Many authors reported that those reactions led to the formation of o-amino-benzylidenehydrazines 1, o-arylideneamino-2-arylidenehydrazines 2, 2-substituted-3-arylideneamino-1,2 -dihydroquinazolin-4(3H)-ones 3 or 1,2,4-triazepin-5-ones 4, depending on reaction conditions, the substituents used, and proportions of the reagents [6][7][8][9][10] .…”

New Compounds: Synthesis of 2-Amino-5H-1,3,4-benzotriazepin-5-ones

“…Anthranilohydrazides bearing a methyl on the amide-lie nitrogen (i.e., N-methyl-2-aminobenzohydrazides, I) were obtained by the opening of isatoic anhydride with methylhydrazine (13, 14). These hydrazides condensed instantaneously in chilled ethanol with cyanogen bromide (Scheme I) to give IIa-IIg in 36-8596 yield.…”

2-Amino-N′-phenylbenzohydrazide

“…The synthesis of the 2-amino-N′-phenylbenzohydrazide 2 was done starting of isatoic anhydride (1H-benzo [d] [1,3]oxazine-2,4-dione) (Leiby & Heindel 1976;Iwakura et al, 1976), which was treated with phenyl hydrazine in DMF at reflux by 2 h to give an 82% yield. The product was crystallized in ethyl acetate with melting point 227-228 °C.…”

“…For the synthesis of the starting material 1H-benzo[d] [1,3]oxazine-2,4-dione, see: Iwakura et al (1976); Leiby & Heindel (1976). For hydrogen-bond motifs, see: Bernstein et al (1995).…”