SITE-SELECTIVE DIELS-ALDER REACTIONS OF 7-(METHOXYIMINO)-4-METHYLCHROMENE-2,8-DIONE WITH ALKENES

Authors
NICOLAIDES DN BEZERGIANNIDOUBALOUCTSI C AWAD RW LITINAS KE MALAMIDOUXENIKAKI E TERZIS A RAPTOPOULOU CP
Citation
Dn. Nicolaides et al., SITE-SELECTIVE DIELS-ALDER REACTIONS OF 7-(METHOXYIMINO)-4-METHYLCHROMENE-2,8-DIONE WITH ALKENES, Journal of organic chemistry, 62(3), 1997, pp. 499-502
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
3
Year of publication
1997
Pages
499 - 502
Database
ISI
SICI code
0022-3263(1997)62:3<499:SDRO7>2.0.ZU;2-O
Abstract
Regio- and site-selective Diels-Alder reactions of o-quinone monooxime 1 are reported. The electron rich dienophiles 2, 4, 6, 8, and 10 reac t with the exocyclic diene system of monooxime 1 leading to the coumar in derivatives 3, 5, 7, 9, 11, and 12. The electron deficient dienophi les 13a,b and 18 react with the quinoid and the pyrone diene systems o f compound 1 affording the cycloadducts 14a,b, 17a,b, and 19.