Name: Pyridine-3,5-dicarbonitrile. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about A study of solvent effect on photochemically induced reactions between pyridinedicarbonitriles and alkenes: an easy approach to the synthesis of cyclopenta[b or c]pyridines. Author is Bernardi, Rosanna; Caronna, Tullio; Luogo, Daniela dal Pio; Morrocchi, Sergio; Poggi, Gabriella; Vittimberga, Bruno M..
Photochem. induced reactions of pyridinedicarbonitriles and alkenes showed an interesting dependence on solvent polarity. In non-polar solvents ipso-substitution of the cyano groups in positions α or γ to the heterocyclic nitrogen occurred to a larger extent, while in polar solvents the reaction provided a path to the formation of a new ring between the carbon atom of one of the cyano groups and a ring position, forming a cyclopenta[b]pyridine or cyclopenta[c]pyridine derivatives Studies on the multiplicity of the excited state controlling the reaction showed that the singlet state was involved in the ipso-substitution, while the triplet state controlled the formation of the pyridine. An explanation for the solvent effect was given in terms of shift of the excited states with the solvent used. Theor. calculations justified the position of the cyclization, although no correlation was found for the regioisomers ratio. This reaction represented an effective entry to the biol. interesting pyrindine systems.
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