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Communication | Regular issue | Vol 26, No. 3, 1987, pp.625-631
Published online, 1st January, 1970
DOI: 10.3987/R-1987-03-0625
Heteroanalogous Dezapurines via Novel 4+2 Cycloaddition Reactions of Ketenimines

Gert Kollenz, Gerhard Penn, Walter Ott, Karl Peters, Eva-Maria Peters, and Hans Georg von Schnering

*Isotope Department, Institut fur Organische Chemie, Karl-Franzens-Universitat Graz, Heinrichstr. 28, A-8010 Graz, Austria


The heterocyclic 2,3-diones 1 and the ketenimines 2 combine yielding heteroanalogous deazapurines 4, 6 and 7 partly having so far unknown molecular skeletons, which were made evident with aid of X-ray structure analyses (6b,7a). IR- and 13C NMR measurements. The reaction pathways include 4+2 cycloaddition processes across the C=N-bond of the ketenimine, accompanied by several surprising rearrangements. These are the first examples observed of 4+2 cycloaddition reactions with ketenimines of to oxa-1,3-dienes.