Action des hydroxyurées sur les maléate et fumarate de méthyle. Obtention des carbométhoxy-5 oxa-6 dihydrouraciles; transposition en carbométhoxyméthylène-5 hydantoïnes

Bennouna, C.; Petrus, Francoise; Verducci, Jean; Hauw, C.; Gaultier, J.

doi:10.1139/v81-420

Cited by 2 publications

(2 citation statements)

References 7 publications

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“…Ammonia and primary and secondary amines can be added to isocyanates to give ureas; this is again an excellent method. The methodology for obtaining of N -hydroxy ureas is simply modified by using hydroxylamine free base …”

Section: Nitrosocarbonyl Precursors Reactivity and Trappingmentioning

confidence: 99%

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Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

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The nitrosocarbonyls (R-CONO) are highly reactive species and remarkable intermediates toward different synthetic targets. This review will cover a research area whose impact in current organic synthesis is constantly increasing in the chemical community. This review represents the first and comprehensive picture on the generation and trapping of nitrosocarbonyls and is solidly built on more than 380 papers. Six different classes of key starting materials such as hydroxamic acids, N-hydroxy carbamates, N-hydroxyureas, nitrile oxides, and 1,2,4-oxadiazole-4-oxides were highlighted. The content of the review surveys all the methods to generate the nitrosocarbonyls through different approaches (oxidative, thermal, photochemical, catalytic, aerobic, and the less common ones) in the light of efficiency, yields, and mildness. The most successful trapping agents employed to catch these fleeting intermediates are reviewed, exploiting their superior dienophilic, enophilic, and electrophilic power. The work is completed by paragraphs dedicated to the detection of the intermediates, theoretical studies, and insights about the challenges and future directions for the field.

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Section: Nitrosocarbonyl Precursors Reactivity and Trappingmentioning

confidence: 99%

“…The methodology for obtaining of N-hydroxy ureas is simply modified by using hydroxylamine free base. 36 2.1.4. Nitrile Oxides.…”

Section: Nitrosocarbonyl Precursors Reactivity and Trappingmentioning

confidence: 99%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

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ChemInform Abstract: EFFECT OF HYDROXYUREAS ON METHYL MALEATE AND FUMARATE. PREPARATION OF 5‐CARBOMETHOXY‐6‐OXADIHYDROURACILS; TRANSPOSITION TO 5‐CARBOMETHOXYMETHYLENE HYDANTOINS

Bennouna¹,

Petrus²,

Verducci³

et al. 1982

Chemischer Informationsdienst

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In Gegenwart von Triethylamin entsteht aus Dimethylmaleat (II) oder ‐fumarat durch eine Michael‐Addition mit dem Hydroxyharnstoff (Ia) ein Gemisch (Ausb. 40%) der Produkte (IIIa) und (IVa) (RG: P21/c, Z=4) im Verhältnis 40: 60. Der Einsatz einer stärkeren Base wie Methanolat liefert bereits nach 30 min überwiegend (IVa), das nach 24 h vollständig in das Hydantoin (Va) umgewandelt ist, sowie den Bernsteinsäureester (VI) als Nebenprodukt.

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Action des hydroxyurées sur les maléate et fumarate de méthyle. Obtention des carbométhoxy-5 oxa-6 dihydrouraciles; transposition en carbométhoxyméthylène-5 hydantoïnes

Cited by 2 publications

References 7 publications

Generation and Trapping of Nitrosocarbonyl Intermediates

Generation and Trapping of Nitrosocarbonyl Intermediates

ChemInform Abstract: EFFECT OF HYDROXYUREAS ON METHYL MALEATE AND FUMARATE. PREPARATION OF 5‐CARBOMETHOXY‐6‐OXADIHYDROURACILS; TRANSPOSITION TO 5‐CARBOMETHOXYMETHYLENE HYDANTOINS

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