By usingamulti-parameterapproach(acombinationofHammett/Ingold-Yukawa-Tsuno/Fujita-Nishioka free energyrelationships)themononuclearrearrangementsofheterocycles(MRH)ratesfor five new ortho-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/waterandin a largerangeofpSþ values)havebeenrelatedtotheelectronicandproximityeffectsexertedbythe present substituents,alsoconsideringpreviousresultsonsomemono meta- and para-substituted(Z)- arylhydrazones.Ineverycase,excellentcorrelationcoefficients havebeencalculated(r2 or R2 0.996). Once morethestudyofMRHhasfurnishedaninterestingpanelofdifferentreactivity(threepathwaysof reaction havebeenevidenced:general-base-catalyzed,uncatalyzed,andspecific-acid-catalyzed)andthis has beenusefulinenlighteninghowpolysubstitutioncandifferentlyaffecttheMRHrates.Moreover2,6- disubstitutiononthe(Z)-arylhydrazonomoietycausesasignificantincreaseofthereactivityinallofthe three studiedpathways.Allofthecollecteddataappearusefulforunderstandingstructure-reactivity/ activity relationshipsinpolysubstitutedcompounds.
D'Anna, F., Frenna, V., Lanza, C.Z., Macaluso, G., Marullo, S., Spinelli, D., et al. (2010). 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. TETRAHEDRON, 5442-5450 [10.1016/j.tet.2010.05.025].
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
D'ANNA, Francesca;FRENNA, Vincenzo;MACALUSO, Gabriella;MARULLO, Salvatore;
2010-01-01
Abstract
By usingamulti-parameterapproach(acombinationofHammett/Ingold-Yukawa-Tsuno/Fujita-Nishioka free energyrelationships)themononuclearrearrangementsofheterocycles(MRH)ratesfor five new ortho-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/waterandin a largerangeofpSþ values)havebeenrelatedtotheelectronicandproximityeffectsexertedbythe present substituents,alsoconsideringpreviousresultsonsomemono meta- and para-substituted(Z)- arylhydrazones.Ineverycase,excellentcorrelationcoefficients havebeencalculated(r2 or R2 0.996). Once morethestudyofMRHhasfurnishedaninterestingpanelofdifferentreactivity(threepathwaysof reaction havebeenevidenced:general-base-catalyzed,uncatalyzed,andspecific-acid-catalyzed)andthis has beenusefulinenlighteninghowpolysubstitutioncandifferentlyaffecttheMRHrates.Moreover2,6- disubstitutiononthe(Z)-arylhydrazonomoietycausesasignificantincreaseofthereactivityinallofthe three studiedpathways.Allofthecollecteddataappearusefulforunderstandingstructure-reactivity/ activity relationshipsinpolysubstitutedcompounds.
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