Heterocyclic and aromatic amines

The chromatographic behaviomr of the aromatic amines is closely related to that of the aliphatic amities. A good, sharply defined separation is especially valuable here also for following rapidly chemical changes in organic syntheses. 

Sihca gel G layers and benzene-methanol (95 + 5) solvent have proved the best for TLC of the amines mentioned below. The following hi /-values have been obtained aniline 38, p-xylidine 44, jS-naphthyl-amine 44, acridine 50, carbazole 58, diphenylamine 69 [38]. 

Hansson and Alm [10] have separated diphenylamine, triphenyl-amine and the corresponding nitroso- and nitro derivatives on silica gel 6 layers, using toluene, benzene or chloroform. 

Mistryxjkov [18] has chromatographed fmrw-decahydroqiiinoline, as-deca-hydroquinoline, (l)-cw-perhydropyridine, their derivatives and some aromatic amines he used loose alumina layers and various neutral or basic solvents such as acetone-methanol-water (72 + 18 + 9) and chloroform (saturated with ammonia)-benzene (50 + 50). 

The thin-layer chromatographic separation of positionally isomeric primary amines is of interest. Waksmxjndzki and co-workers [48] have separated o-, m- and p-nitroanUine, for example, with chloroform the kB/-values were 84, 73, and 58, respectively. Amine isomers have been separated also by Gillio-Tos et al. [7], using standard conditions. 

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PospfSil, J.i Aromatic and Heterocyclic Amines in Polymer Stabilization, Vol. 124, pp. 87-190. 

Weisburger JH (2002) Comments on the history and importance of aromatic and heterocyclic amines in public health. Mut Res 506-507 9-20... 

Gorlewska-Roberts KM, Teitel CH, Lay JO, Jr., et al. Lactoperoxidase-catalyzed activation of carcinogenic aromatic and heterocyclic amines. Chem Res Toxicol 2004 17(12) 1659-1966. 

Modifications of the Bratton-Marshall method mentioned in Section IV.D.3.g can be used for sensitive spectrophotometric detection and determination of primary aromatic and heterocyclic amines. Thus, a simple spectrophotometric determination of the cardioprotective agent acadesine (142) was developed, to measure concentrations of the drug in plasma during intravenous infusion to patients undergoing coronary artery bypass graft surgery336. 

The fuel selected for use with HAN should be totally compatible and therefore, nitrate salts of amines are the natural choice for this purpose. Based on a study with aliphatic, aromatic and heterocyclic amines, aliphatic amines are considered a better choice and a formulation containing the nitrate salt of triethanolamine (TEA), that is, TEAN [(CH2OHCH2)3 NHNOJ is currently in use. HAN-based propellants consist of HAN, water and TEAN. Some typical formulations of LGP are given in Table 4.2 along with their properties. These three propellants differ from one another only in respect of the amount of water which they contain. 

Acetyl transferases Aromatic and heterocyclic amines, hydrazines, and sulfonamides... 

Among N-donor ligands, ammonia, aliphatic, aromatic, and heterocyclic amines are widely used as ligands at present (see Sec. 2.2.4.2). Amine complexes are obtained by direct (immediate) interaction of ligands and metal salts, for example (3.8) [8] ... 

As a result of interaction of 843 and pyridine, the adduct 845 is formed [53], The structures of coordination compounds 844 and 845 were proved by x-ray diffraction. As shown above (Sec. 3.4.3.2), the direct ammonia synthesis [55,56] with participation of various ligands (especially aliphatic, aromatic, and heterocyclic amines, aminoalcohols), elemental metals (or their oxides), and NH4SCN in mostly non-aqueous media, opens definite possibilities for obtaining thiocyanate complexes. In this respect, transformation (4.9) should be mentioned [57] ... 

The resulting alkyl or aryl diethyl phosphates were selectively detected at the 10-25 ng level with the P-mode FPD. Similarly, Jacob et al (36) used dimethyl thiophosphinic chloride in the presence of excess triethylamine to convert primary aliphatic, aromatic and heterocyclic amines to the corresponding N-dimethyl-thiophosphinic amides. The excess reagent was easily removed by treating the reaction mixture with methanol-sodium hydrogen car-... 

Pospfsil J (1995) Aromatic and heterocyclic amines in polymer stabilization, Adv Polym Sci 124 87-189. 

Aromatic and heterocyclic amines are generally known by historical names. Phenylamine is called aniline, for example, and its derivatives are named as derivatives of aniline. 

An example of a QSAR model for the prediction of the mutagenic activity of aromatic and heterocyclic amines in the Ames strain TA100 is shown in Figure 1. 

Reactions which formally involve the oxidation of azides have been reviewed by Boyer. Other oxidations with useful synthetic applications include two which start from nitrogen ylides. Sulfimides (50) derived from electron-deficient aromatic and heterocyclic amines are oxidized to the corresponding nitroso compounds by MCPBA. - This is a very useful method of preparation of some otherwise inaccessible nitroso compounds such as 2-nitrosopyridine and 1-nitrosoisoquinoline. They can be further oxidized, for example by ozone, to the nitro compounds. Phosphimides (51) are oxidized directly by ozone to the nitro compounds, although the nitroso compounds are intermediates. Isocyanates can also be oxidized to the corresponding nitro compounds, by dimediyldioxiraiK (1). ... 

The same group has also repotted a multicomponent Hantzsch protocol which provided access to polycyclic indenoheterocycles 78 utilizing a variety of aromatic and heterocyclic amines (Scheme 19) [45]. Some of the compounds disclosed showed apoptosis-inducing activity in a human T-cell leukemia cell line similar to etoposide. One of the most potent analogs was compound 79 (Scheme 19) which showed greater than 30% induction of apoptosis at 25 pM, as assessed in a flow cytometric aimexin V/propidium iodide assay in Jurkat cells. 

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