Carbonyl amination

Supplement 1942 195-449 Hydroxy-amines Aminoethyl alcohol, 274. Carbonyl-amines Aminoacetaldehyde, 307. Aminoacetone, 314. Hydroxy-carbonyl amines Glucosamine, 328. Aminocarboxylic acids Glycine, 333. Hydroxylamines, 534. Hydrazines, 546. Azo Compounds. 562. Oryano-metallic Compounds, 580. 

Supplement 1951 1872-1928 Hydroxy-carbonyl amines, 233. Amino-carboxylic acids Anthranilic acid (o-aminobenzoicacid). 310. Amino-hydroxy-carboxylic acids, 577. Amino-sulphonic acids Sulphanilio acid, 695. 

S.08.4.2.1 Synthesis of diaziridines by electrophilic amination of carbonyl-amine adducts... 

Fig. 12.—Carbonyl-amine reactions leading to Maillard reaction products and reductones (adapted from Ref. 51a).

The objective was to engineer a catalytic carbonylation-amination-Michael addition cascade employing carbon monoxide (1 atm). This cascade, if viable, could, conceptually, proceed via either of two pathways (Scheme 9). 

Scheme 14.—Formation of A-Substituted Aldosylamine by the Carbonyl-Amine Reaction.. ...

Hidalgo FJ and Zamora R (1993) Fluorescent pyrrole products from carbonyl-amine reactions. J Biol Chem 268, 16190-16197. 

In creating synthetic routes for the development of drug molecules, the synthetic chemist wants to create a molecular entity in which functional groups (carbonyls, amines, etc.) are correctly positioned in three-dimensional space this will enable the creation of functional biophoric fragments such as the pharmacophore. The synthetic chemist has ten general classes of reactions available for such synthetic tasks ... 

This procedure illustrates a general method for the preparation of rearranged allylic amines from allylic alcohols.2,3 The method is experimentally simple and has been used to prepare a variety of allylic prim-, sec-, and tert-carbonyl amines as illustrated in Table I. The only limitation encountered so far is a competing ionic elimination reaction which becomes important for tri-chloroacetimidic esters of 3-substituted-2-cyclohexen-l-ols.3 4 The rearrangement is formulated as a concerted [3,3]-sigmatropic rearrangement on the basis of its stereo- and regiospecificity3,5 which are... 

In general the presence of certain chemical groups are known to introduce stiffness into molecules. These groups include aromatic moieties, carbonyls, amines and amides. Other groups are believed to introduce flexibility into compounds. In general, the flexibilizing character is believed to increase as follows... 

The synthetic routes may often involve template directed condensations, a widely used reaction being the (carbonyl + amine) to imine condensation that efficiently leads to a variety of Schiff-base macrocycles [2.58-2.60, A.7, A.14], macrobicyclic cryptands [2.61-2.63] and lacunar cyclidene ligands [2.60, 2.64]. 

Mester, L. Szabados, L. Mester, K. Yadav, H. Maillard type carbonyl-amine reactions in vivo and their physiological effects. Prog. Food Nutr. Sci. 1981, 5 295-314. 

Several mechanisms have been reported for pyrazine formation by Maillard reactions (21,52,53). The carbon skeletons of pyrazines come from a-dicarbonyl (Strecker) compounds which can react with ammonia to produce ot-amino ketones as described by Flament, et al. (54) which condense by dehydration and oxidize to pyrazines (Figure 6), or the dicarbonyl compounds can initiate Strecker degradation of amino acids to form ot-amino ketones which are hydrolyzed to carbonyl amines, condensed and are oxidized to substituted... 

Carbonyl-amine reactions, such as those between lactose and milk proteins, have been reported to produce potent antioxidants (Dugan, 1980 Eichner, 1980 Ericksson, 1982). Browning reaction products can stabilize milk fat considerably (Wyatt and Day, 1965). However, it is important to note that browning reaction products may exert adverse nutritional and toxicological effects (O Brien and Morrissey, 1989). 

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