On the use of multi-parameter free energy relationships: the rearrangement of (Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole into (2-aryl-5-phenyl-2H-1,2,3-tryazol-4-yl)ureas

Francesca D'Anna, Vincenzo Frenna, Gabriella Macaluso, Salvatore Marullo, Gabriella Macaluso, Salvatore Marullo, Camilla Zairalanza, Vincenzo Frenna, Francesca D'Anna, Giovanni Petrillo, Domenico Spinelli, Raffaella Spisani

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17 Citazioni (Scopus)

Abstract

By usingamulti-parameterapproach(acombinationofHammett/Ingold-Yukawa-Tsuno/Fujita-Nishiokafree energyrelationships)themononuclearrearrangementsofheterocycles(MRH)ratesfor five newortho-substitutedandtennewdi-,tri-,ortetra-substituted(Z)-arylhydrazonesof5-amino-3-benzoyl-1,2,4-oxadiazoleintotherelevant(2-aryl-5-phenyl-2H-1,2,3-triazol-4-yl)ureas(indioxane/waterandina largerangeofpSþ values)havebeenrelatedtotheelectronicandproximityeffectsexertedbythepresent substituents,alsoconsideringpreviousresultsonsomemono meta- and para-substituted(Z)-arylhydrazones.Ineverycase,excellentcorrelationcoefficients havebeencalculated(r2 or R2 0.996).Once morethestudyofMRHhasfurnishedaninterestingpanelofdifferentreactivity(threepathwaysofreaction havebeenevidenced:general-base-catalyzed,uncatalyzed,andspecific-acid-catalyzed)andthishas beenusefulinenlighteninghowpolysubstitutioncandifferentlyaffecttheMRHrates.Moreover2,6-disubstitutiononthe(Z)-arylhydrazonomoietycausesasignificantincreaseofthereactivityinallofthethree studiedpathways.Allofthecollecteddataappearusefulforunderstandingstructure-reactivity/activity relationshipsinpolysubstitutedcompounds.
Lingua originaleEnglish
pagine (da-a)5442-5450
Numero di pagine9
RivistaTetrahedron
Stato di pubblicazionePublished - 2010

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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