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RESEARCH PRODUCT
Ru(bpy)2Cl2: A catalyst able to shift the course of the photorearrangement in the Boulton-Katritzky reaction
Licia ViggianiVincenzo FrennaDomenico SpinelliAntonio Palumbo-piccionelloMagda MonariMaurizio D'auriaRocco Racioppisubject
RegiochemistryRuthenium catalystDrug Discovery3003 Pharmaceutical ScienceOrganic ChemistryRegioselectivityRuthenium catalystPhotochemistryDFTBiochemistryCatalysischemistry.chemical_compoundchemistryPhotochemical rearrangementDrug Discovery124-OxadiazoleAcetonitriledescription
The Boulton-Katritzky reaction represents one of the most popular and efficient strategies used to realize azole-into-azole conversions. For example, under different experimental conditions, it allows the rearrangement of Z-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazoles (1) into 2-aryl-4-benzoylamino-5-phenyl-2H-1,2,3-triazoles (2) in very high yields. Moreover, we have recently realized this conversion also by UV-photostimulation. Now we have enlarged the scope of the reaction irradiating with visible or UV light an acetonitrile solution of some Z-arylhydrazones (1a-e) in the presence of catalytic amounts of Ru(bpY)(2)Cl-2. We have observed the unexpected formation of the 1-aryl-5-benzoylamino-3-phenyl-1,2,4-triazoles (3a-e) eventually together with the expected 2a-d in high yields. (C) 2015 Elsevier Ltd. All rights reserved.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-11-01 |