Dipole-Stabilized Carbanions in Series of Cyclic Aldonitrones. Part 2: Reactions of the Metalated Aldonitrones—Derivatives of 3-Imidazoline 3-Oxide and 2 H-Imidazole 1-Oxide with Aldehydes and Ketones

Abstract

Metalated aldonitrones of 3-imidazoline 3-oxide and 2 H-imidazole 1-oxide series react with a wide variety of aldehydes and ketones leading to the unknown α-hydroxymethyl nitrones. Reaction of 2,2-dimethyl-4-phenyl-2 H-imidazole 1-oxide with allylacetone spontaneously lead to tricyclic 3,3,8-trimethyl-1-phenyl-5a,6,7,8-tetrahydro-3 H,5 H-4-oxa-2,3a-diaza-cyclopenta[ c]pentalen-8-ol. The hydroxy group of (1,2,2,5,5-pentamethyl-2,5-dihydro-1H-imidazol-3-oxide-4-yl)phenylmethanol is substituted with piperidine to give, after further transformations, (1,2,2,5,5-pentamethyl-2,5-dihydro-1 H-imidazol-4-yl)phenylmethanone.