A. Stukalov, V.V. Sokolov, V.V. Suslonov, M.A. Kuznetsov
“Pyrazoles and C-Imidoylaziridines through [4+1] Annulation and [2+1] Cycloaddition of 1-Azabuta-1,3-dienes with a Synthetic Equivalent of Phthalimidonitrene”
Eur. J. Org. Chem., 2017, 2587-2595
Oxidative addition of N-aminophthalimide to 1,2,4-triaryl-1-azabuta-1,3-dienes leads, in most cases, to the regiodefined formation of 1,3,5-triarylpyrazoles in moderate to good yields through [4+1] annulation. This transformation is supposed to proceed by nitrenoid attack onto a lone pair of electrons of the imine nitrogen atom to give the vinylazomethine imine, followed by its 1,5-electrocyclization into pyrazoline and further aromatization into pyrazole. Rare examples of 2-imidoyl-1-phthalimidoaziridines that are formed by competitive [2+1] cycloaddition onto the C=C bond were isolated in low yields for 1-azadienes with electron-deficient aryl substituents at the imine nitrogen atom.