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On the dichotomic behavior of the Z-2,4-dinitrophenylhydrazone of 5-amino-3-benzoyl-1,2,4-oxadiazole with acids in toluene and in dioxane/water: rearrangement versus hydrolysis.
MedLine Citation:
PMID:  15575748     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The mononuclear rearrangement (MRH) of the Z-2,4-dinitrophenylhydrazone (4a) and of the Z-phenylhydrazone (4b) of 5-amino-3-benzoyl-1,2,4-oxadiazole into the relevant triazoles 5a and 5b in toluene has been quantitatively investigated in the presence of trichloroacetic acid (TCA) and of piperidine at 313.1 K. While the behavior in the presence of piperidine recalls the one previously evidenced for some Z-hydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole, the study of the reactivity in the presence of TCA has most interestingly evidenced a general-acid-catalyzed rearrangement for "both" 4a and 4b. Thus, 4a offers the first example of a solvent-dependent dichotomic behavior in MRH processes on 1,2,4-oxadiazole derivatives as far as it undergoes an "acidic hydrolysis" in dioxane/water and a "rearrangement" in toluene.
Authors:
Francesca D'Anna; Vincenzo Frenna; Gabriella Macaluso; Stefano Morganti; Patrizia Nitti; Vitalba Pace; Domenico Spinelli; Raffaella Spisani
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Dec 
Date Detail:
Created Date:  2004-12-03     Completed Date:  2005-02-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8718-22     Citation Subset:  -    
Affiliation:
Dipartimento di Chimica Organica E. Paterno, Università degli Studi di Palermo, Viale delle Scienze, Parco d'Orleans 2, 90128 Palermo, Italy.
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