Imines reaction with amines

Reactions with Amines and Amides. Hydroxybenzaldehydes undergo the normal reactions with aUphatic and aromatic primary amines to form imines and Schiff bases reaction with hydroxylamine gives an oxime, reaction with hydrazines gives hydrazones, and reactions with semicarbazide give semicarbazones. The reaction of 4-hydroxybenzaldehyde with hydroxylamine hydrochloride is a convenient method for the preparation of 4-cyanophenol (52,53). 

The A-acetyl derivatives of the 2-alkylthio-l,3-thiadiazol-4-imines (124, R = SR, R = Ac) undergo nucleophilic displacement reaction with amines (benzylamine, cyclohexylamine, morpholine, or aniline) giving the 2-amino derivatives (124, R = NRj, R = Ac). The salt (126, R = R = Ph, R = R = H, X = Cl) reacts with aniline at room temperature giving 4-anilino-2-phenyl-l,3-thiazole (128), presumably by a mechanism involving cleavage of the heterocyclic ring. ... 

The free carbonyl function of this ligand may undergo further condensation reactions. With amines RNH2, products [PdLL l are obtained where both L and L may be N,N -bonded chelates (42 R = Me, Et, Pr, Bu)264,265 or L may be bonded through N(imine) and 0(oxime) (43 R = H).266 Similar linkage isomerism is seen for other oximato ligands of this type.267... 

VI. REACTIONS WITH AMINES, IMINES, AND PROTIC SOLVENTS.. 203... 

From 2-bromobenzaldehyde, isoindolinones and 3-alkylphthalides are obtained by reaction with amines " (imines ) and 1,3-dicarbonyl compounds, respectively. Alkyl aroates are similarly accessible from aryl tosylates, but the scope is very limited, as only 4-acetylphenyl tosylate furnishes acceptable yields. ... 

Some modifications of amino and hydrazino groups were also performed. An amino group can be replaced in the reaction with amines, although in low yield. To the few known pyridazinonimines some new compounds have been added. The imines (203) are prepared from the corresponding pyridazinium salts and sodium hydride. Hydrazinopyridazines upon nitrosation are transformed into azido- or tetrazolopyrida es. The reaction can be complicated by aza-transfer reactions with a heterocyclic diazo compound. For example, 3-chloro-6-hydrazinopyridazine, when treated with... 

A one-pot transformation of 3-(dimethoxymethyl)-A-cyanothiazolidin-2-imine into 1,3,5-tri-azine-2,4-diamines can be achieved by reaction with amines. The reactions are conducted in refluxing toluene and the yields vary from 28-90%.480... 

Over the last decade, a considerable number of reactions has been studied (11,35) (i) olefins oxidation (38,39), hydroboration, and halogenation (40) (ii) amines silylation (41,42), amidation (43), and imine formation (44) (iii) hydroxyl groups reaction with anhydrides (45), isocyanates (46), epichloro-hydrin and chlorosilanes (47) (iv) carboxylic acids formation of acid chlorides (48), mixed anhydrides (49) and activated esters (50) (v) carboxylic esters reduction and hydrolysis (51) (vi) aldehydes imine formation (52) (vii) epoxides reactions with amines (55), glycols (54) and carboxyl-terminated polymers (55). A list of all the major classes of reactions on SAMs plus relevant examples are discussed comprehensively elsewhere (//). The following sections will provide a more detailed look at reactions with some of the common functional SAMs, i.e hydroxyl and carboxyl terminated SAMs. 

Reactions with Amines, Imines, Nitroso Oxide, and Protic Solvents... 

FIGURE 16.49 Continuation of reactions from Figure 16.48. In the reaction with water, loss of a proton leads to the recovered carbonyl compound. In the alcohol reaction, there is no proton to be lost, and a second molecule of alcohol adds to give an acetal. In the reaction with amine, loss of a proton leads to an imine. 

Aldehydes and ketones react with ammonia and primary amines to form imines. Reaction with aldehydes yields aldimines, and ketimines arise in reactions with ketones (Figure 8.28). Imines derived from aliphatic carbonyl compounds are generally unstable and are transformed to more stable products, such as amines, diamines and others. Secondary amines react with aldehydes and ketones with the formation of enamines (Figure 8.29). Imines are similarly flavour-active compounds derived from furan-2-carbaldehyde. For example, the aromas of Ar-furfuryl(isobutylidene)amine, N-(furfuryl)isopentyhdeneamine (8-155) and N-(furfurylidene)isobutylamine (8-156) reportedly resemble chocolate. 

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