6,12-METHANODIPYRANO [4,3-B-4,3-F]DIOXOCINE-1,7-DIONE - THE REACTIVITY TOWARDS NITROGEN NUCLEOPHILES

Authors
SVETLIK J HANUS V LAGOJA IM SCHANTL JG
Citation
J. Svetlik et al., 6,12-METHANODIPYRANO [4,3-B-4,3-F]DIOXOCINE-1,7-DIONE - THE REACTIVITY TOWARDS NITROGEN NUCLEOPHILES, Heterocycles, 45(9), 1997, pp. 1833-1838
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
9
Year of publication
1997
Pages
1833 - 1838
Database
ISI
SICI code
0385-5414(1997)45:9<1833:6[-TR>2.0.ZU;2-I
Abstract
The reaction of the title compound (1) with hydrazine hydrate induces a complex ring transformation affording 3,4,6-trimethyl-1H-indazoIe-7- carboxylic acid (2) and (3-methyl-1H-pyrazol-5-yl)acetic acid hydrazid e (3). The product structures have been elucidated by 2D-NMR technique s, and a mechanistic rationalization of this multistep reaction is pre sented. Methylhydrazine converts compound (1) into (1,3-dimethyl-1H-py razol-5-yl)acetic acid (12), while phenyl hydrazine fails to affect 1.