Non-symmetrical allenyl azines and their transformations leading to new heterocyclic skeletons

Abstract

The preparation of new non-symmetrical allenyl azines 5 with aliphatic and alicyclic substituents and their reactions are described. When aldazines 5 were refluxed in xylene formation of bicyclic products 7 was observed. Compounds 7 appeared as derivatives of isowithasomnine. Combined intra-intermolecular criss-cross cycloadditions of azines 5 afforded heterocyclic products 8 and 9 containing three fused five-membered rings. Structures of all new compounds were elucidated by 1 H and 13 C NMR, IR and MS measurements and in some cases by X-ray structure analysis.