Formation of 3,3,5,7-tetranitrooxindole and 3,5,7-trinitroindazole by nitration of oxindole

Bergman, Jan; Bergman, Solveig

doi:10.1016/s0040-4039(96)02139-9

Cited by 15 publications

(5 citation statements)

References 9 publications

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“…Many of them are thermally unstable and easy to decompose. Examples of such decomposition can be found in the literature, − and carbonylation was usually achieved finally. According to 13 C NMR studies, Latypov confirmed that 1 underwent slow decomposition in DMSO to yield finally 5 .…”

Section: Resultsmentioning

confidence: 99%

Study on Reactions of 2-(Dinitromethylene)-4,5-imidazolidinedione

et al. 2004

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Some new reactions of 2-(dinitromethylene)-4,5-imidazolidinedione (1) with water, alcohols, carboxylic acids, and alkalis were discovered. By reaction of 1 with carboxylic acids, large particle size 1,1-diamino-2,2-dinitroethylene (2) was prepared. By reaction of 1 with methanol, the methanol adduct (4) was synthesized and characterized. By reaction of 1 with water, the synthetic pathway of 2-methylimidazole to 2 could be achieved in a continuous process. By reaction of 1 with KOH, 2 and potassium dinitromethane (6) could be formed at different temperature, respectively. Compounds 1 and 4 decomposed into parabanic acid (5), losing nitrogen oxides and carbon oxides. Some explosive properties of 1 were studied. The mechanisms of synthesis of 1, 2, and 5 are discussed.

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Section: Resultsmentioning

confidence: 99%

Study on Reactions of 2-(Dinitromethylene)-4,5-imidazolidinedione

et al. 2004

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“…Trying to overcome these difficulties and to see if the presence of only carbonyl groups could promote gem -dinitration in nitrogen heterocyles we have studied the nitration of several pyrimidinones. Nitric acid in sulfuric acid was chosen as the reaction medium as this had previously been found to favor the formation of gem -dinitro compounds. − …”

Section: Introductionmentioning

confidence: 99%

Nitration of 2-Substituted Pyrimidine-4,6-diones, Structure and Reactivity of 5,5-gem-Dinitropyrimidine-4,6-diones

Langlét¹,

Latypov²,

Wellmar³

et al. 2002

J. Org. Chem.

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“…In recent years attention focused particularly on pernitrated azaheterocycles [2][3][4][5][6] which in some cases can be directly obtained by exhaustive nitration of the corresponding heterocyclic scaffolds [7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

“…The search for new energetic compounds with combined high efficiency and low sensitivity is of considerable current interest [2]. In recent years attention focused particularly on pernitrated azaheterocycles [2][3][4][5][6] which in some cases can be directly obtained by exhaustive nitration of the corresponding heterocyclic scaffolds [7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

On the reaction of 3,4‐dihydropyrimidones with nitric acid. Preparation and x‐ray structure analysis of a stable nitrolic acid

Puchala

Belaj

Kappe

et al. 2001

Journal of Heterocyclic Chem

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A series of substituted 3,4-dihydro-2-pyrimidones (DHPMs) was reacted with nitric acid under different reaction conditions. Treatment of DHPMs with 50-65% nitric acid at 0 °C led to the formation of the corresponding dehydrogenated 2-pyrimidones in moderate to good yields. In contrast, reaction of one representative DHPM with 60% nitric acid at 50 °C led to an unusually stable nitrolic acid, involving a formal nitration, nitrosation, and dehydrogenation step. The molecular structure of this product was determined by X-ray crystallographic analysis

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Formation of 3,3,5,7-tetranitrooxindole and 3,5,7-trinitroindazole by nitration of oxindole

Cited by 15 publications

References 9 publications

Study on Reactions of 2-(Dinitromethylene)-4,5-imidazolidinedione

Study on Reactions of 2-(Dinitromethylene)-4,5-imidazolidinedione

Nitration of 2-Substituted Pyrimidine-4,6-diones, Structure and Reactivity of 5,5-gem-Dinitropyrimidine-4,6-diones

On the reaction of 3,4‐dihydropyrimidones with nitric acid. Preparation and x‐ray structure analysis of a stable nitrolic acid

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