Preparation of 6-, 7-, and 9-substituted derivatives of 2-oxa-1,3,4,10-tetraazacyclopenta[b]fluoren-9-one

Citation
Ld. Bratton et al., Preparation of 6-, 7-, and 9-substituted derivatives of 2-oxa-1,3,4,10-tetraazacyclopenta[b]fluoren-9-one, J HETERO CH, 38(5), 2001, pp. 1103-1111
Citations number
13
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
5
Year of publication
2001
Pages
1103 - 1111
Database
ISI
SICI code
0022-152X(200109/10)38:5<1103:PO67A9>2.0.ZU;2-N
Abstract
The preparation of a variety of derivatives of 2-oxa-1,3,4,10-tetraazacyclo penta[b] fluoren-9-one 1 is described. A series of substituted indan-1-ones were prepared and oxidized with N-bromosuccinimide and dimethyl sulfoxide to the corresponding ninhydrin derivatives. Cyclization of the ninhydrins w ith furazan-3,4-diamine yielded the target tetracycles. Appropiate choice o f substituents in ninhydrins led to a preference for one regioisomer in the target tetracycles. This permitted the synthesis of a variety of 8-substit uted heterocycles. In those instances where isomer formation was possible, structural assignments were confirmed by X-ray crystallography.