Reactions of Ethyleneimine with Aldehydes and Ketones¹

The Oxazolidines.

“…It should be added that the condensation of aliphatic aldehydes with ethanolamine (106) or ethylenimine (42) leads to products which, according to their molecular refraction, contain certain amounts (5-15 per cent) of Schiff bases. TAtiLHo Per cent of Schiff base in some aliphatic oxazolidines (7, t The product obtained from amyl methyl ketone and ethylenimine (42) appears to be wholly cyclic.…”

Combining photochemistry and catalysis: rapid access to sp3 – rich polyheterocycles from simple pyrroles

“…There have been a number of reports of the reaction of aldehydes with aziridines in a [3 + 2] manner, but with few exceptions 11 these all involved activated aziridines under Lewis acid catalysis. 12 We were intrigued to discover whether our strained aziridines would undergo [3 + 2] cycloadditions with aldehydes under the aforementioned optimised Pd-catalysed conditions.…”

Imines, Cyclic

“…Half aminals can be converted to full aminals by reaction with a further secondary amine, isomerized to oxazolidines by the action of heat or used in a Mannich reaction for the ring aminomethylation of phenols, although this reaction gives only moderate yields (218)(219)(220)(221)(222)(223)(224)(225)(226)(227).…”