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Site-Selective Diels-Alder Reactions of 7-(Methoxyimino)-4-methylchromene-2,8-dione with Alkenes
D. N. Nicolaides1, C. Bezergiannidou-Balouctsi, R. Wajih Awad
1National Research Center of Physical Sciences "Demokritos", 15310, Aghia Paraskevi, Attiki, Greece.
The Journal of Organic Chemistry
|February 7, 1997
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 react with the exocyclic diene system of monooxime 1 leading to the coumarin derivatives 3, 5, 7, 9, 11, and 12. The electron deficient dienophiles 13a,b and 18 react with the quinoid and the pyrone diene systems of compound 1 affording the cycloadducts 14a,b, 17a,b, and 19.