Journal of Organic Chemistry p. 3419 - 3425 (1991)
Update date:2022-07-29
Topics:
Hassner, A.
Fischer, B.
We report the first examples of intramolecular Diels-Alder addition of heterodienophiles N=N, C=N, C=O, C=S to oxazoles.The required 5-ethoxy- and 5-phenyloxazoles were synthesized bearing a side chain of variable length on C-2 to which the different heterodienophiles are attached.The products of the thermal bis heteroannulation are 3-triazolines, imidazolines, oxazolines, or thiazolines fused to a five- to six-membered ring.Relative reactivities were established and the mechanism is discussed.
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