1,3- vs. 1,5-cyclization of azomethine ylides derived from 1-azabuta-1,3-dienes and difluoro- and dichlorocarbenes. Experimental and quantum-chemical study

Хлебников, А. Ф.; Новиков, Михаил С.; Dolgikh, Stanislav A.; Magull, J.

doi:10.3998/ark.5550190.0009.909

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Cited by 12 publications

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Pyrazoles and C‐Imidoylaziridines through [4+1] Annulation and [2+1] Cycloaddition of 1‐Azabuta‐1,3‐dienes with a Synthetic Equivalent of Phthalimidonitrene

et al. 2017

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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.

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