Novel Heterocycles by Bis Heteroannulation of Oxazoles

A. Hassner, B. Fischer

Research output: Contribution to journalArticlepeer-review

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Abstract

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.

Original languageEnglish
Pages (from-to)3419-3425
Number of pages7
JournalJournal of Organic Chemistry
Volume56
Issue number10
DOIs
StatePublished - 1 May 1991

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