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

Leiby, Robert W.; Heindel, Ned D.

doi:10.1002/jps.2600660444

Cited by 10 publications

(2 citation statements)

References 8 publications

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“…As was shown in Scheme 10, the use of hydrazonoyl halides allows the introduction of specific substituents to the C 2 carbon atom and to the N 4 nitrogen atom of benzotriazepine 26a . Since the methods known from several earlier publications for the synthesis of benzotriazepines from isatoic anhydride derivatives without the use of hydrazonoyl halides allow one to obtain N 4 H (R = H, 59 %; R = Br, 74 %) IV [51] or hydrobromic salt N 4 Me (36–85 %) V [52] substituted benzotriazepinones (Figure 2).…”

Section: Hydrazonoyl Halides In the Synthesis Of Six‐ And Seven‐membe...mentioning

confidence: 99%

Advances in the Synthesis of Heterocycles with Two and Three Heteroatoms using Hydrazonoyl Halides

Yamaletdinova,

Gataullin

2024

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the use of hydrazonoyl halides in the synthesis of five‐ (pyrazoles, thiazoles, triazoles, oxa‐ and thiadiazoles), six‐ (oxa‐ and thiadiazines, indazoles, pyridazines, pyrazines, tetrazines) or seven‐membered (benzotriazepine) heterocycles. In the formation of these heterocycles, the main intermediate stage of the reaction is the in situ generation of nitrilimine, which enters into a cycloaddition reaction with substituted acetylenes (including in situ generated benzynes, naphthynes), allenes, activated olefins, anthranilic acid derivatives, organosulfur compounds (mercaptoaldehydes, mercaptocarboxylic acids ) or with fused heterocycles. Examples are given of the formation of heterocycles by replacing the halogen atom from a hydrazonoyl halide molecule with a nucleophilic group, followed by exhaustive intramolecular cyclization into the target compound. There are discussions of reactions in which the cycloaddition of the nitrilimine to the in situ synthesized Knoevenagel condensation product (from CH‐acid compounds, such as di‐ and monocarbonyl compounds, dinitrile malonic acid) occurs, leading to spiro‐linked or conventional pyrazoles. Some syntheses of biologically active representatives are shown.

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Section: Hydrazonoyl Halides In the Synthesis Of Six‐ And Seven‐membe...mentioning

confidence: 99%

Advances in the Synthesis of Heterocycles with Two and Three Heteroatoms using Hydrazonoyl Halides

Yamaletdinova,

Gataullin

2024

Helvetica Chimica Acta

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“…Generally, the most common and well-established approach to synthesize 1,3,4-benzotriazepinones is the condensation reaction of 2-aminobenzoyl hydrazines with orthoesters (Scheme a) . Cyanogen bromide and chloroformate have also been demonstrated to be effective in this condensation reaction with 2-aminobenzoyl hydrazines for synthesizing 1,3,4-benzotriazepinones. Moreover, the cyclodesulfurization of 2-aminobenzoyl hydrazines with isothiocyanates has been reported to be another approach for the synthesis of 1,3,4-benzotriazepinones .…”

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confidence: 99%