Dipole-stabilized carbanions in series of cyclic aldonitrones. Part 2: Reactions of the metalated aldonitrones - Derivatives of 3-imidazoline 3-oxideand 2H-imidazole 1-oxide with aldehydes and ketones

Metalated aldonitrones of 3-imidazoline 3-oxide and 2H-imidazole 1-oxide se ries react with a wide variety of aldehydes and ketones leading to the unkn own alpha-hydroxymethyl nitrones. Reaction of 2,2-dimethyl-4-phenyl-2H-imid azole 1-oxide with allylacetone spontaneously lead to tricyclic 3,3,8-trime thyl-1-phenyl-5a,6,7,8-tetrahydro-3H,5H-4-oxa-2,3a-diaza-cydopenta[c]pental en-8-ol. The hydroxy group of (1,2,2,5,5-pentamethyl-2,5-dihydro-1H-imidazo l-3-oxide-4-yl)phenylmethanol is substituted with piperidine to give, after further transformations, (1,2,2,5,5-pentamethyl-2,5-dihydro-1H-imidazol-4- yl)phenylmethanone. (C) 2000 Elsevier Science Ltd. All rights reserved.