1975
DOI: 10.1021/jo00901a008
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Synthesis of 3,4-dihydro-1H-1,3,4-benzotriazepine-2,5-diones

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Cited by 57 publications
(16 citation statements)
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“…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] ).…”
Section: Resultssupporting
confidence: 67%
See 1 more Smart Citation
“…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] ).…”
Section: Resultssupporting
confidence: 67%
“…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] .…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Reaction Of a Diamine Chain With A Carbonyl Donormentioning
confidence: 91%
“…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.…”
Section: Intramolecular Reaction Of a Carboxylic Acid Derivative Withmentioning
confidence: 99%
“…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].…”
mentioning
confidence: 99%