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- Title
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.
- Authors
Tzinavou, Alexandra; Dolka, Chrysanthi; Tsoungas, Petros G.; Van der Eycken, Erik; Van Meervelt, Luc; Varvounis, George
- Abstract
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.
- Subjects
BENZENE compound synthesis; OXIDATION; NITRATION; CERIUM compounds; NITRONAPHTHALENES
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2017, Vol 2017, p41
- ISSN
1551-7004
- Publication type
Article
- DOI
10.3998/ark.5550190.0018.300