Journal of Organic Chemistry p. 3568 - 3572 (1988)
Update date:2022-08-02
Topics:
Taylor, Edward C.
Pont, Joseph L.
Warner, John C.
7-Azalumazines tethered at the C6 position with a series of dienophilic side chains undergo intramolecular Diels-Alder reactions to provide 6,7-annulated lumazines and 8-deazalumazines.The rates of these cycloaddition reactions are markedly faster than for previously reported cycloadditions of isomeric C7-tethered 6-azalumazines.On the other hand, 7-azalumazines do not undergo intermolecular Diels-Alder reactions with enamine dienophiles, whereas under identical conditions, 6-azalumazines react readily.Reasons for this striking reversal in reactivity observed for inter- and intramolecular Diels-Alder reactions of 6- vs 7-azalumazines are discussed.
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