Anilino acids

Other intermediates for the synthesis of diazomethane are nitrosomethyl-urea, CH,N(NO)CONHj, and nitrosomethylurethane, CH,N(NO)COjCjH,. Certain a-anilino acids like phenylglycine and a-anilinopropionic acid have been converted to their N-nitroso derivatives. ... 

Anilino acids. Derivatives formed by substitution of the aromatic amine, as an ammonia compound, into the hydrocarbon radical of an organic acid. 

Aniline acting as ammonia forms derivatives analogous to these called anilino acids. 

Quistad et al. (1983), studied the elimination of " CF-labeled fluvalinate, and discovered that the hydroxy acid (CAS no. 82186-86-5), anUino acid (CAS no. 76338-73-3), glycine conjugate of the anilino acid, haloaniline (CAS no. 39885-50-2) and the sulfate of hydroxyhaloaniline (CAS no. 84960-10-1) were excreted in urine. Fluvalinate, hydroxyacid, anilino acid, and anilino acid conjugates were found in feces. According to Quistad et al. (1983), the ratio of fecal to urinary elimination is higher for fluvalinate than for fenvalerate (Kaneko et al. 1981b Ohkawa et al. 1979), deltamethrin (Cole et al. 1982 Ruzo et al. 1978), cypermethrin (Cole et al. 1982), and tralomethrin (Cole et al. 1982). 

Anilides or p-toluidides of acids from esters. Esters are converted into the corresponding anilides or p-toluidides by treatment with anilino- or with p-toluidino-magnesium bromide, which are readily obtained from any simple Grignard reagent and aniline or p-toluidine ... 

Another category Ic indole synthesis involves cyclization of a-anilino aldehydes or ketones under the influence of protonic or Lewis acids. This corresponds to retro.synthetic path d in Scheme 4.1. Considerable work on such reactions was done in the early 1960s by Julia and co-workers. The most successful examples involved alkylation of anilines with y-haloacetoacetic esters or amides. For example, heating IV-substituted anilines with ethyl 4-bromoacetoacetate followed by cyclization w ith ZnClj gave indole-3-acetate esterfi]. Additional examples are given in Table 4.3. 

The nitration of the 2-anilino-4-phenylselenazole (103) is much more complicated. Even careful nitration using the nitrate-sulfuric acid method leads to the formation of a mixture of variously nitrated compounds in an almost violent reaction. By the use of column chromatography as well as thin-layer chromatography a separation could be made, and the compounds could be partly identified by an independent synthesis. Scheme 33 shows a general view of the substances prepared. Ring fission was not obser ed under mild conditions. 

POPOP p-bis[2-(5-phenyloxazoyl)]benzene. t ANS, anilino-8-naphthalene sulfonic acid. t TNS, 2-p-toluidinylnaphthalene-6-sulfonate. 

Other disazo dyes with good substantivity and high wet-fastness properties on polyamides are Acid Red 114 (40), made by coupling o-toHdine to phenol which is then coupled to G-acid, followed by reaction of the phenoHc hydroxyl group with -toluenesulfonyl chloride, and Acid Blue 113 (41) (metanilic acid — 1-naphthylamine — 8-anilino-1-naphthalenesulfonic acid). 

Triazole-4-carboxylic acid, 5-anilino-anthelmintic activity, 5, 732... 

The preparation and use of derivatized Meldrum s acid has led to an alternative preparation of 2-substituted quinolines (49 and 50) and the preparation of pyridopyrimidines (52). When Meldrum s acid derivatives are used (as shown in this example) decarboxylation occurred under the cyclization conditions. Three component coupling has been used to readily assemble the desired 3-anilino-acrylate from reaction of Meldrum s acid, (EtO)3CH and an aniline (e.g. 54 or 55).< ... 

In connection with the biological activity of s-triazines, Burchfield and Storrs investigated the reaction of 2,4-dichloro-6-(o-chloro-anilino)-s-triazine with over sixty amino acids, peptides, and related... 

Dichloro-l,3,5-triazanaphthalene and its 6-methyl derivative react at the 4-position (70-90% yields) with ammonia in dioxane (20°, 15 min) or in water (95°, 1.5 hr) and with diethylamine in dioxane (20°, 15 min). The dichloroazine yields the 4-(A-ethyl-anilino)-2-chloro derivative under acidic conditions. Amination of the 2,4-dithioxo derivative with concentrated ammonia (95°,... 

Base-catalyzed Dimroth rearrangements of l-aryl-4,6-diamino-1,3,5-triazines or triflic acid-induced decomposition of 6-anilino-1,3,5-triazines led to the formation of the corresponding substituted 1,2-dihydro-l,3,5-triazines, whose structure was established on the basis of H NMR spectra (93JHC849). 

Common Name 2-[3-(trifluoromethyl)anilino] nicotinic acid Structural Formula cr... 

Nitron was prepd in 1905 by M. Busch by heating N,-anilino-N,Nf-diphenylguanidine with 90% formic acid in a press tube at 175° (Ref 2). Other methods are given in Ref 1... 

X-anilino)-pent-3-en-2-ones in sulphuric acid at 25 °C377... 

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