Imidazolidine ring

The conjugate addition of lithium cuprates to cinnamates 1 bearing a chiral oxazolidine or imidazolidine ring at the ortho position produced 2 in good to excellent yield upon hydrolysis14. 

Resting cells of bacterium Stenotrophomonas maltophilia CGMCC 1.1788 catalyze the stereoselective hydroxylation at position C12 of imidacloprid (IMl) in the imidazolidine ring to form (R)-5-hydroxy IML Under acidic conditions, 5-hydroxy IMI is converted into olefin IMl (Figure 12.2), which exhibits about 19 times more insecticidal efficacy than IMI against horsebean aphid imago. 

Soil. The most important metabolic steps were oxidation at the imidazolidine ring, reduction or loss of the nitro group, hydrolysis to 6-chloronicotinic acid and mineralisation. Medium adsorption to soil, imidacloprid and soil metabolites are to be classified as immobile... 

Unfortunately, no transition metal complex was synthesised, although the combination of a pendant OH functionality and chirality in the backbone of the imidazolidin ring holds great promise for asymmetric homogenous catalysis. 

Formylphenyl ethyl tellurium was obtained by lithiation of 1,3-dimethyl-2-phenylimidazolidine, reaction of the lithiated product with diethyl ditellurium, and hydrolytic cleavage of the imidazolidine ring. ... 

An interesting route to the imidazolidine ring exploits a reaction of dichlorocarbene, generated by the action of potassium ferf-butoxide on... 

Condensation reactions of aromatic aldehydes with a,cu-polyamines lead to Schiff bases, if the polyamine involved contains only primary amino groups or to imidazolidines, if the polyamine contains a secondary amino group. Condensation of 2-pyridinecarboxaldehyde 7V-oxide with triethylenetetramine yields derivative (31), with two imidazolidine rings, which in the presence of Cu11 undergoes a ring-opening reaction due to the formation of a complex.42... 

Eine ahnliche Umlagerung ist an 2-(3-Nitro-2-oxo-imidazolidino)-l,3-thiazoI moglich, wobei die Nitro-Gruppe aus dem Imidazolidin-Ring in die 5-Position des 1,3-Thiazols wan-dert1262 ... 

In this case, diethylenetriamine acts as a trinucleophile its interaction with amino enone 71 involves double nucleophilic addition at the /1-carbon, forming ammonia, and an attack at the carbonyl group, liberating water. The reaction takes place when the compound contains a polyfluoroalkyl substituent, not only enhancing the electrophilicity of the /1-carbon atom, but also stabilizing the imidazolidine ring. 

M. Ogata, R. Shimizu, and H. Abe, New degradation product of spiradoline mesylate in aqueous solution Formation of an imidazolidine ring, J. Pharm. Sci. 82, 91-94 (1993). 

Imidazolidine ring closure and opening Modified Curtius degradation... 

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