SYNTHESIS AND REACTIVITY OF MICHAEL ADDUCTS OF LITHIATED 2,5-DIMETHOXY-N-PIVALOYLANILINES AND ARYLIDENEMALONATES

Authors
FERRER P AVENDANO C SOLLHUBER M
Citation
P. Ferrer et al., SYNTHESIS AND REACTIVITY OF MICHAEL ADDUCTS OF LITHIATED 2,5-DIMETHOXY-N-PIVALOYLANILINES AND ARYLIDENEMALONATES, Tetrahedron, 53(9), 1997, pp. 3231-3242
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
9
Year of publication
1997
Pages
3231 - 3242
Database
ISI
SICI code
0040-4020(1997)53:9<3231:SAROMA>2.0.ZU;2-O
Abstract
Michael addition of lithiated 2,5-dimethoxypivaloylaniline to diisopro pyl arylidenmaionates, followed by acid cyclization, affords 5,8-dimet hoxy-4-aryl-3,4-dihydro-2(1H)quinolinines (5). These compounds are ver y inert to the 3,4-dehydrogenation, but were easily transformed to 4-a ryl-3,4-dihydro-(1H)quinoline-2,5,8-triones (10) which, through Diels- Alder heterocyclization, gave 4-aryl-3,4-dihydro- 1,8-diazaanthracene- 2,9,10-triones (16). (C) 1997 Elsevier Science Ltd.