Fig. Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion.They are used in 1,3-dipolar cycloaddition reactions to form 5-membered heterocycles, including pyrrolidines and pyrrolines. First, the amine nitrogen attacks the carbonyl carbon in a nucleophilic addition step (step 1) which is closely analogous to hemiacetal and hemiketal formation. When a crude imine, which was prepared from ene-aldehyde and primary amine in the presence of MgSO4, was treated with Cp2ZrBu2 at room temperature overnight, cyclopentane derivative having trans-substituents was obtained in high yield along with a small amount of cyclopentane derivative having cis-substituents.

The reaction of aldehydes and aqueous ammonia with epoxides leads to imines bearing a vicinal hydroxyl group regioselectively. The concern about the mechanism that we agree on doesn't really have a bearing on this answer.

Biomol. ... formation of an imine.

It is well known that ketenes reacts with imines to produce 2-azetidinones by a [2 + 2] cycloaddition.

Two mechanistic pathways can be proposed to explain the formation of compounds 4.The first one involves an initial aza-Wittig reaction between the iminophosphorane function and the ketene to give a imino-ketenimine intermediate 5 that undergoes intramolecular [2 + 2] cycloaddition.It is well known that ketenes reacts with imines to produce 2-azetidinones by a [2 + 2] cycloaddition. Intramolecular imine formation. The addition of azomethine imine 5b to nitroalkene 2a (Scheme 2b), follows a similar mechanistic pathway, but the second step (the nucleophilic addition of the generated nitronate to the C=N bond) does not proceed since the intramolecular nucleophilic addition to the imine is blocked by the phenyl group. Intramolecular carbinolamine and imine formation with cobalt(III)-amine complexes. Reactions of Primary Amines with Aldehydes and Ketones (review of Chapter 17) Reaction type: Nucleophilic Addition then Elimination. Photolysis and thermolysis of bis(imino)pyridine cobalt azides: C-H activation from putative cobalt nitrido complexes In aqueous solution an intramolecular condensation occurs between a 1,2-diaminoethane ligand and the carbaldehyde group, in the aldehyde complex to give the tridentate imine product [Co(en){NH2(CH2)2N= CHCH2NH2 }Cl] 2+.

Tetrahydrochromano[4,3‐ b ]quinolines are formed with high exo‐E‐anti selectivity and yields up to 87 % when a nitrobenzene and a 2‐(cinnamyloxy)benzaldehyde are reacted in aqueous citric acid by using iron as a reductant and montmorillonite K10 as a catalyst.
New imine based rod-like compounds, composed of three-benzene-ring molecular core linked with azomethine as well as ester groups and terminated with (… Summary.

The imine group acts as a directing group as well as an intramolecular nucleophile for the first time in intramolecular CN bonds formation reactions.

… An atom-economic approach to synthesize 1,2,4-trisubstituted pyrroles through palladium-catalyzed imine-directed intramolecular C(sp³)H amination reaction has been developed. Both imine and enamine formation are nucleophilic addition to the carbonyl. New imine based rod-like compounds, composed of three-benzene-ring molecular core linked with azomethine as well as ester groups and terminated with (… Here, we describe a new one-pot method to synthesize 4,7-substituted pyrrolo[1,2-a]quinoxalines and related heterocyles through a cascade of redox reactions/imine formation/intramolecular cyclization. T. Kondo, T. Okada, T.-A. Am.


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