Preparation of 9-amino-1,9-diazatricyclo[b.4.0.0(4,8)]dodecane-2,10-dione by a retro-Diels-Alder Reaction

Authors
Stajer, G Miklos, F Sohar, P Sillanpaa, R
Citation
G. Stajer et al., Preparation of 9-amino-1,9-diazatricyclo[b.4.0.0(4,8)]dodecane-2,10-dione by a retro-Diels-Alder Reaction, EUR J ORG C, (21), 2001, pp. 4153-4156
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
21
Year of publication
2001
Pages
4153 - 4156
Database
ISI
SICI code
1434-193X(200111):21<4153:PO9B>2.0.ZU;2-J
Abstract
Treatment of di-endo- or di-exo-3-aminobicyclo[2.2.1]hept-5-ene-2-carbohydr azides (1a and 1b) with ethyl 2-(2-oxocyclopentyl)acetate (2) yields norbor nene-condensed 9-amino-1,9-diazatricyclo[6.4.0.0(4.8)]dodecane -2,10-diones 3a and 3b; the condensed bis(lactams) 4a and 4b and (from 1b and 2) the cy clopenta[c]pyridazinone 5. After separation, 3a and 3b both decompose on he ating by loss of cyclopentadiene to give 9-amino-1,9-diazatricyclo[6.4.0.0( 4.8)]dodecane-2,10-dione (6).