Synthesis of 3,4-dihydro-1H-1,3,4-benzotriazepine-2,5-diones

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

“…Structure IV, formed as a result of that rearrangement, is not stable and, after translocation of the hydrogen atom from the carbonyl oxygen atom, transforms into compound 17, which is the product of this reaction chain. Another sequence of intermediate compounds leading to formation of the product is also plausible (as previously reported by N. P. Peet and S. Sunder [6] ; F. Fülöp [11] ).…”

“…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] .…”

Synthetic Methods for the Preparation of Triazepandiones and Review of their Applications

“…However, all these results have been re-examined and contradicted. Peet and Sunder [12] investigated the cyclization of 2-aminobenzoylhydrazine in presence of urea and showed that the reaction did not lead to 1,3,4-triazepan-2,5-dione (9) as described previously, they proposed the 3-amino-1H-quinazoline-2,4-dione 10 to be the product of the reaction (Scheme 3), so did Davidson [13] and Martin and colleagues [14]. Scheme 1.…”

“…Two different methods were developed by Peet and Sunder [12]. The first strategy involved the treatment of 2-carboalkoxyphenyl isocyanate with methyl hydrazine to give Scheme 5.…”

A Facile Synthesis of Substituted 3‐Amino‐1H‐quinazoline‐2,4‐diones.

“…The first reported synthesis involved a reaction of hydrazine hydrate with a 3H-quinazolinedione under harsh conditions [2]. Other reported approaches include reaction of t-butyl carbazate with isatoic anhydride [3], treatment of 2-aminobenzoylhydrazine with urea [4], ring contraction of the 7-membered 1,3,4-benzotriazepine-2,5-dione ring with sodium hydroxide [5], and reaction of 4-oxo-4H-3,1benzoxazine-2-carbonitrile with hydrazine hydrate [6].…”