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Note | Regular issue | Vol 45, No. 9, 1997, pp.1833-1838
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7894
6,12-Methanodipyrano[4,3-b:4,3-f]dioxocine-1,7-dione: The Reactivity towards Nitrogen Nucleophiles

Jan Svetlik,* Vladimir Hanus, Irene M. Lagoja, and Joachim G. Schantl

*Department of Analytical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, SK-83232 Bratislava, Slovakia


The reaction of the title compound (1) with hydrazine hydrate induces a complex ring transformation affording 3,4,6-trimethyl-1H-indazole-7-carboxylic acid (2) and (3-methyl-1H-pyrazol-5-yl)acetic acid hydrazide (3). The product structures have been elucidated by 2D-NMR techniques, and a mechanistic rationalization of this multistep reaction is presented. Methylhydrazine converts compound (1) into (1,3-dimethyl-1H-pyrazol-5-yl)acetic acid (12), while phenyl hydrazine fails to affect 1.