1- Aminonaphthalene

When the parent molecules connected by the azo group are different, azo is placed between the complete names of the parent molecules, substituted or unsubstituted. Locants are placed between the affix azo and the names of the molecules to which each refers. Preference is given to the more complex parent molecule for citation as the first component, e.g., 2-aminonaphthalene-l-azo-(4 -chloro-2 -methy Ibenzene). 

Naphthionic acid (4-aminonaphthalene-l-sulfonic acid) [84-86-6] M 223.3, m > 300°(dec), pK 2.68. It crystallises from H2O as needles of the 0.5 hydrate. Salt solns fluoresce strongly blue. 

The formation of l-methyl-5-aminonaphthalene when dihydro-lysergic acid is fused with potassium hydroxide requires rings (A) and (Cb The presence of an indole nueleus (rings (A) and (B) ) is established by the formation of 3 4-dimethylindole, m.p. 115-7°, pierate, m.p. 185-7°, by decarboxylation of an indole acid obtained when dihydrolysergic acid is fused with potassium hydroxide. ... 

The feasibility of this approach was demonstrated with a model library of 36 compounds prepared from a combination of three Boc protected L-amino acids (valine 23, phenylalanine 24, and proline 25) and 12 aromatic amines (3,4,5-trimethoxyaniline (26), 3,5-dimethylaniline (27), 3-benyloxyaniline (28), 5-aminoindane (29), 4-tert-butylamline (30), 4-biphenylamine (31), 1-3-benyloxyani-line (28), 5-aminoindane (29), 4-tert-butylaniline (30), 4-biphenylamine (31), 1-aminonaphthalene (32), 4-tritylaniline (33), 2-aminoanthracene (34),... 

Alternatively, the thiazolotriazine ring was prepared from l-nitro-2-aminonaphthalene with an isothiocyanate to give naphthylpyrimidine 669, whose reaction with phenacyl bromide gave thiazoline 670. Reduction with stanous chloride and cyclization with (V-bromosuccinimide gave naphthothiazolotriazine 671 (74JIC631) (Scheme 138). 

Naph thy (amines. See under Aminonaphthalenes and Derivatives in Vol 1, A237-L to A238-L... 

A bacterial strain BN6 oxidizes 5-aminonaphthalene-2-sulfonate by established pathways to 6-amino-2-hydroxybenzalpyruvate that undergoes spontaneous cyclization to 5-hydroxy-quinoline-2-carboxylate (Figure 2.2a) (Nortemann et al. 1993). 

FIGURE 2.2 Transformation of (a) 5-aminonaphthalene-2-sulfonate, (b) benzo[fc]thiophene, (c) 4-chloro-biphenyl, (d) 4-nitrotoluene, (e) 3,5-dichlor-4-methoxybenzyl alcohol, (f) 2,3-diaminonaphthalene in presence of nitrate, and (g) 3,4-dichloroaniline presence of nitrate. 

Nortemann B, A Glasser, R Machinek, G Remberg, H-J Knackmuss (1993) 5-hydroxyquinoline-2-carboxylic acid, a dead-end metabolite from the bacterial oxidation of 5-aminonaphthalene-2-sulfonic acid. Appl Environ Microbiol 59 1898-1903. 

An analogous pathway is used for the degradation of 5-aminosalicylate that is an intermediate in the degradation of 6-aminonaphthalene-2-sulfonate. Direct ring fission of both 5-aminosalicylate and 5-hydroxysalicylate can be accomplished by a salicylate 1,2-dioxygenase in Pseudaminobacter salicylatoxidans (Hintner et al. 2001). 

Aromatic azo compounds, many of which are sulfonated, are components of many commercially important dyes, colorants, and pigments, so that attention has been directed to their degradation and transformation. These compounds are often considered recalcitrant, although then-transformation has been accomplished by reduction to amines with scission of the Ar-N=N-Ar bond to produce arylamines. The amines may then be degraded, for example, 6-aminonaphthalene-2-sulfonate by dioxygenation and ring fission to 5-aminosalicylate (Hang et al. 1991). This is then... 

Haug W, A Schmidt, B Nortemann, DC Hempel, A Stolz, H-J Knackmuss (1991) Mineralization of the sulfonated azo dye mordant Yellow 3 by a 6-aminonaphthalene-2-sulfonate-degrading bacterial consortium. Appl Environ Microbiol 57 3144-3149. 

In addition, the formation of terminal metabolites may be adverse either for the organism itself, or for other organisms in the ecosystem. Microbial metabolites may also undergo purely chemical reactions to compounds that are terminal products. Examples include the formation of 5-hydroxyquinoline-2-carboxylate from 5-aminonaphthalene-2-sulfonate (Nortemann et al. 1993) or benzo[fc]naphtho[l,2- /]thiophene from benzothiophene (Kropp et al. 1994). Microbial metabolites may be toxic to both the bacteria producing them and to higher organisms. Illustrative examples of toxicity include the following ... 

Chiesa, C. and Horvath, Cs., Capillary zone electrophoresis of malto-oligosac-charides derivatized with 8-aminonaphthalene-l,3,6-trisulfonic acid,. Chromatogr., 645, 337, 1993. 

The formation of complexes of the fluorescent tracer dye ammonium 1-phenyl-aminonaphthalene-8-sulphonate (10.41) with cyclodextrins has been investigated with favourable results, especially in environmental studies [33]. The ability of this dye to complex with cyclodextrins has been exploited mainly as an analytical tool in the study of cyclodextrin applications, since its fluorescence is easily measured. The interaction of a-, P-and y-cyclodextrins with azo acid dyes containing alkyl chains of different lengths has been reported [36,37]. The formation and isolation of solid complexes between P-cyclodextrin and Cl Acid Red 42, Cl Acid Blue 40 or Erionyl Bordeaux 5BLF (Ciba) have been reported [29]. 

Seliskar C, Brand L (1971) Electronic spectra of 2-aminonaphthalene-6-sulfonate and related molecules. II. Effects of solvent medium on the absorption and fluorescence spectra. JACS 93 5414-5420... 

As a diazonium component, aniline sulfonic acid may occasionally be replaced by 2-aminonaphthalene-l-sulfonic acid or by aniline. 

Anthanthrone is synthesized from naphthostyril (105), which is saponified to form l-aminonaphthalene-8-carboxylic acid (106). Naphthostyril itself is prepared from 1-naphthylamine with phosgene in the presence of dry aluminum chloride. 

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