Cerium(IV) ammonium nitrate for the tandem nitration and oxidative rearrangement of 2-Acetyl-1-naphthol benzoylhydrazones into 1,2-diacylnaphthalenes; synthesis of benzo[f]phthalazines

A novel nitration and oxidation reaction sequence of 2-Acetyl-1-naphthol benzoylhydrazones with CAN is presented. There is strong indication that nitration precedes an oxidative rearrangement to 1,2-diacyl-4- nitronaphthalenes or oxidative electrocyclisation to 3-methyl-5-nitronaphtho[2,1-d]isoxazole. Condensation of 1,2-diacyl-4-nitronaphthalenes with hydrazine hydrate yields 1,4-disubstituted benzo[f]phthalazines.

Authors
Tzinavou A.1 , Dolka C.1 , Tsoungas P.G.2 , Van Der Eycken E. , Van Meervelt L. , Varvounis G.5
Journal
Arkivoc
Number of issue
3
Language
English
Pages
41-54
Status
Published
Link
External link
DOI
10.3998/ARK.5550190.0018.300
Volume
2017
Year
2017
Organizations
  • 1 Department of Chemistry, Section of Organic Chemistry and Biochemistry, University of Ioannina, Ioannina, 45110, Greece
  • 2 Department of Biochemistry, Hellenic Pasteur Institute, 127 Vas. Sofias Ave., Athens, 11521, Greece
  • 3 Department of Chemistry Katholieke Universiteit Leuven, Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 4 Peoples Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
  • 5 Biomolecular Architecture, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
Keywords
Benzoylhydrazones; Benzo[f]phthalazines; Cerium(IV) ammonium nitrate; Electrocyclisation; Nitration; Oxidative rearrangement
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