On the rearrangement of some Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles into 2-aryl-4-phenacyl-2H-1,2,3-triazoles: a kinetic study of the substituent effects in Boulton-Katritzky reactions

Vincenzo Frenna, Antonio Palumbo Piccionello, Franco Ghelfi, Domenico Spinelli

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4 Citazioni (Scopus)

Abstract

The rearrangement of eight new Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles (3d–k) into the relevant 2-aryl-4-phenacyl-2H-1,2,3-triazoles (4d–k) in dioxane/water solution at different proton concentrations has been quantitatively studied in a wide temperature range (293–333 K). The data collected together with some our previous ones on compounds 3a–c have allowed a deep study of the substituent effects on the course of the rearrangement, thus increasing our knowledge on the Boulton–Katritzky reactions in isoxazole derivatives and on the temperature effects on free energy relationships
Lingua originaleEnglish
pagine (da-a)7315-7322
Numero di pagine8
RivistaTetrahedron
Volume71
Stato di pubblicazionePublished - 2015

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Isoxazoles
Triazoles
Thermal effects
Free energy
Protons
Derivatives
Kinetics
Temperature
Water
1,4-dioxane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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title = "On the rearrangement of some Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles into 2-aryl-4-phenacyl-2H-1,2,3-triazoles: a kinetic study of the substituent effects in Boulton-Katritzky reactions",
abstract = "The rearrangement of eight new Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles (3d–k) into the relevant 2-aryl-4-phenacyl-2H-1,2,3-triazoles (4d–k) in dioxane/water solution at different proton concentrations has been quantitatively studied in a wide temperature range (293–333 K). The data collected together with some our previous ones on compounds 3a–c have allowed a deep study of the substituent effects on the course of the rearrangement, thus increasing our knowledge on the Boulton–Katritzky reactions in isoxazole derivatives and on the temperature effects on free energy relationships",
author = "Vincenzo Frenna and {Palumbo Piccionello}, Antonio and Franco Ghelfi and Domenico Spinelli",
year = "2015",
language = "English",
volume = "71",
pages = "7315--7322",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",

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TY - JOUR

T1 - On the rearrangement of some Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles into 2-aryl-4-phenacyl-2H-1,2,3-triazoles: a kinetic study of the substituent effects in Boulton-Katritzky reactions

AU - Frenna, Vincenzo

AU - Palumbo Piccionello, Antonio

AU - Ghelfi, Franco

AU - Spinelli, Domenico

PY - 2015

Y1 - 2015

N2 - The rearrangement of eight new Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles (3d–k) into the relevant 2-aryl-4-phenacyl-2H-1,2,3-triazoles (4d–k) in dioxane/water solution at different proton concentrations has been quantitatively studied in a wide temperature range (293–333 K). The data collected together with some our previous ones on compounds 3a–c have allowed a deep study of the substituent effects on the course of the rearrangement, thus increasing our knowledge on the Boulton–Katritzky reactions in isoxazole derivatives and on the temperature effects on free energy relationships

AB - The rearrangement of eight new Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles (3d–k) into the relevant 2-aryl-4-phenacyl-2H-1,2,3-triazoles (4d–k) in dioxane/water solution at different proton concentrations has been quantitatively studied in a wide temperature range (293–333 K). The data collected together with some our previous ones on compounds 3a–c have allowed a deep study of the substituent effects on the course of the rearrangement, thus increasing our knowledge on the Boulton–Katritzky reactions in isoxazole derivatives and on the temperature effects on free energy relationships

UR - http://hdl.handle.net/10447/146693

UR - https://www.sciencedirect.com/science/article/pii/S0040402015004822

M3 - Article

VL - 71

SP - 7315

EP - 7322

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

ER -