About: Some New Information on the Formation of Substituted 4-Amino-1-Substituted Phenyl-1H-Pyrazoles from beta-Enaminones and Diazonium Tetrafluoroborates     Goto   Sponge   NotDistinct   Permalink

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  • Upon reaction of 2-methyl-, 3-ethoxycarbonyl, and 4-ethoxycarbonylbenzenediazonium tetrafluoroborate with 1-cyclopropyl-3-phenylaminohex-2-en-1-one 3-cyclopropylcarbonyl-1-(substituted phenyl)-5-ethyl-4-phenylamino-1H-pyrazoles are formed. On the other hand, the reaction of 1-cyclopropyl-3-phenylaminohex-2-en-1-one and 5-methylaminohept-4-en-3-one with sterically more demanding 2-ethoxycarbonylbenzenediazonium tetrafluoroborate does not give the corresponding pyrazoles but the probable intermediates on the route to the pyrazoles: 1-cyclopropyl-3-phenyliminohexane-1,2,4-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone) and 3-methyliminoheptane-2,4,5-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone), respectively. All the compounds were identified on the basis of 1H-/13C-NMR spectra. The structure of 1-cyclopropyl-3-phenyliminohexane-1,2,4-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone) was confirmed by 15N-NMR spectra and X-ray. The bis(2-ethoxycarbonylphenylhydrazones) were found to show atropoisomerism.
  • Upon reaction of 2-methyl-, 3-ethoxycarbonyl, and 4-ethoxycarbonylbenzenediazonium tetrafluoroborate with 1-cyclopropyl-3-phenylaminohex-2-en-1-one 3-cyclopropylcarbonyl-1-(substituted phenyl)-5-ethyl-4-phenylamino-1H-pyrazoles are formed. On the other hand, the reaction of 1-cyclopropyl-3-phenylaminohex-2-en-1-one and 5-methylaminohept-4-en-3-one with sterically more demanding 2-ethoxycarbonylbenzenediazonium tetrafluoroborate does not give the corresponding pyrazoles but the probable intermediates on the route to the pyrazoles: 1-cyclopropyl-3-phenyliminohexane-1,2,4-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone) and 3-methyliminoheptane-2,4,5-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone), respectively. All the compounds were identified on the basis of 1H-/13C-NMR spectra. The structure of 1-cyclopropyl-3-phenyliminohexane-1,2,4-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone) was confirmed by 15N-NMR spectra and X-ray. The bis(2-ethoxycarbonylphenylhydrazones) were found to show atropoisomerism. (en)
Title
  • Some New Information on the Formation of Substituted 4-Amino-1-Substituted Phenyl-1H-Pyrazoles from beta-Enaminones and Diazonium Tetrafluoroborates
  • Some New Information on the Formation of Substituted 4-Amino-1-Substituted Phenyl-1H-Pyrazoles from beta-Enaminones and Diazonium Tetrafluoroborates (en)
skos:prefLabel
  • Some New Information on the Formation of Substituted 4-Amino-1-Substituted Phenyl-1H-Pyrazoles from beta-Enaminones and Diazonium Tetrafluoroborates
  • Some New Information on the Formation of Substituted 4-Amino-1-Substituted Phenyl-1H-Pyrazoles from beta-Enaminones and Diazonium Tetrafluoroborates (en)
skos:notation
  • RIV/00216275:25310/11:39892209!RIV12-MSM-25310___
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  • Z(MSM0021627501)
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  • 4
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  • 230623
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  • RIV/00216275:25310/11:39892209
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  • BENZOYLACETONE DERIVATIVEs; NMR; SALTS; TAUTOMERISM; BOND LENGTHS; NEUTRON-DIFFRACTION; X-RAY; AZO COUPLING PRODUCTS (en)
http://linked.open.../riv/klicoveSlovo
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  • US - Spojené státy americké
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  • [B4BE21697BD5]
http://linked.open...i/riv/nazevZdroje
  • Journal of Heterocyclic Chemistry
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http://linked.open...v/svazekPeriodika
  • 48
http://linked.open...iv/tvurceVysledku
  • Růžička, Aleš
  • Šimůnek, Petr
  • Macháček, Vladimír
  • Svobodová, Markéta
http://linked.open...ain/vavai/riv/wos
  • 000293745900005
http://linked.open...n/vavai/riv/zamer
issn
  • 0022-152X
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  • 10.1002/jhet.579
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  • 25310
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