ChemInform Abstract: Nitriles in Organic Synthesis: The Reaction of Cinnamonitriles with Cyclohexanone and Acetylacetone.

Abstract

The reaction of 1 a, b with cyclohexanone afforded hexahydronaphthalene derivatives (3a, b). In contrast to the behaviour of 1a, b, cyclohexanone reacts with 4a–c to yield the propenylidenecyclohexanone derivatives (5a–c). The reaction of 1a with acetylacetone gives 4H-pyran 6 and a 1:2-adduct 8a. On treatment of 8a with sodium metal in the presence of dioxane, the pyrano [2, 3-b]pyridine (9a) was obtained. When 1b, c reacted with acetylacetone, the only isolable products were 8b,c. Reaction of 4a with acetylacetone gives acyclic compound 10. This on treatment with basic reagents, gives the pyran derivative (13).