Syntheses of heterocyclic compounds. Part XXXII. Intramolecular 1,3-dipolar cycloadditions of 2-allyloxy- and 2-prop-2-ynyloxy-aromatic aldehyde azines

Abstract

Thermolysis of 2-prop-2-ynyloxy-benzaldehyde and -1-naphthaldehyde azines as well as 2-allyloxy-1-naphthaldehyde azines in NN-diethylaniline causes intramolecular cycloaddition in a bis-[3 + 2] or ‘criss-cross’ fashion of the prop-2-ynyl or allyl group to the azine side-chain.