Diamino triazine derivative

Many supramolecular polymers are derived directly from DNA s nucleobases adenine (A), cytosine (C), guanine (G), and thymine (T) [9]. Although each nucleobase can homodimerize, as described in the previous section, heterodynamic complexation is favored to different degrees. The G-C complex involves three H-bonds, and it is two or three orders of magnitude more stable than the A-T complex, involving only two H-bonds. 2,6-Diamino triazine derivatives strongly associate with thymine, and this pair has formed the basis for many studies. 

This reactivity of A-unsubstituted amino-pyrazoles and -indazoles which can be regarded as 1,3-diamino derivatives has been used to build a great variety of fused six-membered heterocycles such as the 1,2,4-triazine derivatives (540) and (541), the 1,3,5-triazine derivatives (542) and (543), and benzothiadiazines (544). 

Matolcsy, G., M. Hamran, and A. Vegh (1959). Hydrophilic 2,4-diamino-6-chloro-s-triazine derivatives as herbicides. Magyar Kem. Foly., 65 414. 

Diamino-(4//)-1,2,4-triazole hydrochloride (312) reacted in AcOH with 2,2,6-trimethyl-chroman-3,4-dione (311a) to give the pyrano-l,2,4-triazine derivative (194) (32%) (Equation (4))... 

Since riboflavin (RF) is surface-active and possesses a high fluorescence quantum yield, the dye is very suitable for TIR fluorescence measurements at a water/oil interface. For TIR experiments, an aqueous RF solution was poured onto a CCI4 solution containing a diamino-j-triazine derivative (DTT), which acted as a flavin receptor via triple hydrogen bonds. On the basis of fluorescence dynamic measurements of RF adsorbed on a water/oil... 

Similar reactions were performed on 6-substituted ametryn analogs, such as a dealkylated derivative, diamino ametryn (CG-2) A -de-ethyl ametryn (CG-3) and A -de-isopropyl ametryn (CG-4). -Acetylcysteine atrazine (CG-11) and 7 -acetylcysteine diamino triazine (CG-15), the radiolabeled materials isolated from rat, goat, and hen studies, were treated in the same manner. Data suggest that the amino side chain of the triazine molecule, either as A -ethyl or A -isopropyl, was stable under acidic reflux conditions. The 6-position with either thiomethyl or another conjugated functional group was labile and subjected to hydrolysis by 6 N HCl. Thus, ametryn and its conjugated metabolites (possibly with proteins or polypeptides), as well as its corresponding -dealkylated metabolites, after hydrolysis by 6 N HCl, could liberate -dealkylated and hydroxylated triazine derivatives. 

A systematic investigation of various 4,6-diamino-l, 2-dihydro-l-aryl-2-alkyl-s-triazine derivatives was undertaken with the knowledge that cycloguanil is rapidly excreted from the body and that dihydrotriazines are therefore unlikely to induce systemic toxicity by accumulating in other tissues following release from a depot site. Synthetic approaches involved the preparation of macromolecules, amide and urea derivatives, and insoluble salts. Macromolecules, such as the bis[4,6-diamino-l,2-dihydro-2,2-dimethyl-s-triazines] (XVa and b) [70, 71], and amide and urea derivatives including XVI and XVII [51] were devoid of repository activity. 

Recently, Bassani et aL reported the use of hydrogen-bonded tape-like structures to assemble cin-namate derivatives in solution. In this work, a dialkylbarbiturate derivative serves to bind two diamino-triazine units appended with cinnamate chromophores. Of the several structures that may be formed, one places the reactive double bonds in close proximity. A nearly 100-fold enhancement in the dimerization rate constant with respect to solution (at identical concentration) is calculated based on the experimentally determined quantum yields and binding constants. The formation of the -truxillate dimer — unusual in solution — and control experiments in the absence of template or using a di-N-methylated barbiturate substantiate the proposed supramolecular control of photoreactivity. 

The preparation of 3,5-diamino derivatives from 3,5-dithioxotria-zines or from 6-methyl-3,5-dimethylmercapto-l,2,4-triazine was also described. ... 

In contrast to these findings, two independent reports have appeared in which the ultraviolet spectrum of 2-amino-l,3,5-triazine has been interpreted to indicate that this compound exists in the imino form, but the correctness of these conclusions appears doubtful, especially since comparisons were not made with the spectra of the alkylated derivatives. Other investigators have interpreted the ultraviolet spectra of a series of amino- and diamino-1,3,5-triazines to indicate that the amino forms of these compounds predominate. ... 

The catalytic effect of protons, of bifunctional catalysts, and of base is demonstrated in the amination of chloro derivatives of pyridazine, pyrimidine, and s-triazine (Tables V and VI). Anilino-s-triazines containing NH groups act as catalysts in their own formation. The catalytic action of protons on anhino-dechlorination of 2-chloro-4,6-diamino-s-triazine and of 2-amino-4-chloropyrimidine was reported in the classic paper by Banks. ... 

Acenaphtheno[l,2-e][l,2,4]triazolo[4,3-h][l,2,4]triazine 747 was prepared (79AP147) by cyclizing 3-hydrazinoacenaphtheno[l,2-e][l,2,4]tria-zine 746 with formic acid. Reaction of 746 with sugars gave the hydrazones, which cyclized with iron(III) chloride to give 748 (93BCJ00). Similarly, the acetaldehyde derivative of 746 was cyclized to 748. The structure of 748 (R = Me) rather than 747 (R = Me) was deduced by unequivocal synthesis of the latter by condensation of acenaphthenequinone with 3,4-diamino[l,2,4]triazole (Scheme 155). 

Benzo-l,2,3-triazin-4-ones with the general structure 6.54 (X = O, S, or H2) are obtained by diazotization of the appropriate aniline derivatives 6.53 (Scheme 6-38). In polar aprotic solvents (e. g., nitrobenzene) the reverse reaction takes place to give the diazonium ion (for an example see Kullick, 1966). Diazotization of 1,8-diamino-naphthalene yields l-i/-naphthol[l,8-cfe]triazine (6.55 Tavs et al., 1967). In concentrated HC1 the triazine ring is opened again. 

When the diamino salt 9 was treated with the 2,3-furandione 10, it gave the pyrido[l,2,-6][l,2,4]triazinone 11, whose reaction with base gave the respective monobenzoyl derivative (89CB1935). Cyclocondensation of 1,6-diaminopyridines 12 with diacetyl gave [73KGS1266 90JCR(S)186] pyridolf 1,2 b] 1,2,4]triazines 13. On the other hand, reaction with benzil was unsuccessful. 

An unexpected production of 2,4,6-triphenyl-l, 3,5-triazine in the electroreduction of 3,4-diphenyI-l,2,5-thiadiazole 1-oxide has been reported . Synthesis of 1,3-diyne derivatives of 2,4-diamino-l,3,5-triazine, 9a and 9b, has been accomplished by reaction of biguanidine with mono- and di-esters 8a and 8b, respectively <00T1233>. 

Finally, the pyrrolo[2,l-/ [l,2,4]triazine moiety was also encountered in azulene derivatives. Reactions of l,8-diamino-3-phenyl-l-azaazulenium salt 54 with triethyl orthoformate and acetic anhydride gave l-phenyl-2a,3,5-mjzjbenzb. //]jzulcncs 55 and 56. The reaction of the same salt with ethyl pymvate gave 4-acetyl-l-phenyl-2a,3,5-triazabenz[c, /]azulene 14 <2000H(53)323>. 

Diamino-s-triazine-2-oL See Ammeline in Yoi 1, p A273-R and its Dinitramino deriv, Dinitroammeline, p A274-L... 

Biguanides [H2NC( = NH)NHC( = NH)NH2] react with lactones, amides, ortho esters, esters, acid anhydrides and acid chlorides to produce a wide range of 6-substituted 2,4-diamino-1,3,5-triazines (515) (59HC(l3)i). Biguanides with carbodiimides, isothiocyanates and ketones give corresponding melamines, thiones and dihydro derivatives, respectively. 

Like acetonitrile, benzonitrile is a powerful solvent fnr many inorganic and organic materials including some polymers. It can be converted to a large number and variety of derivatives by simple syntheses e.g.. by hydrolysis, it can be converted to either benzoic acid nr benzamicle. The most important reaction is with dicyandiamide to produce 2,4-diamino-6-phenyl-l,3,5-triazine (benzogunnamine) ... 

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