New cycloaddition of diarylazines with 1,2-dehydrobenzene, 1,1,2,2-tetracyanoethylene, and dibenzoylacetylene — Facile synthesis of acridinones, pyrazolidine, and pyridazine derivatives

Abstract

Diarylazines were reacted with 1,2-dehydrobenzene (o-benzyne) to give 10-amino-3-substituted-9(10H)-acridinones. On the other hand, 1,1,2,2-tetracyanoethylene was reacted with diarylazines through Michael addition to yield 5-arylpyrazolidine-3,3,4,4-tetracarbonitriles. On reacting the same azines with dibenzoylacetylene, pyridazine derivatives were obtained via a Diels–Alder reaction.Key words: diarylazines, 1,2-dehydrobenzene, tetracyanoethylene, dibenzoylacetylene.