1.2.4- Triazine, 3-amino-5/6-methyl

Coupling the 2,5-anhydro-o-allonic acid derivative 79 with 6-amino-methyl-l,2,4-triazin-5-ones provided the respective amides 807, which were cyclodehydrated and de-O-blocked to 808 [84JCS(P1)229] (Scheme 212). The 2 -deoxy analogs of 808 were similarly prepared [85JCS(P1)621]. 

Application of a modified Willgerodt reaction to the synthesis of 3-heteryl-quinazolinones gives low yields [2427]. Cyanogen [2996] or imino esters [2106] may be used to cyclize anthranilic acids 1,3,5-triazine is an effective amino-methylating agent for the same kind of substrate [2442]. 

H-Pyrazino[l,2-a][l,3,5]triazine, 2-amino-8-methyl-4,9-dioxo-cis-6,7-diphenyl-6,7,8,9-tetrahydro-... 

Sodium methyl mercaptide in xylene was reported to react (25°, 2 hr) in a stepwise fashion with 3,5-dichloro-as-triazine to yield the 3-methylthio-5-chloro and then (70°, 2 hr) the 3,5-bis-methylthio derivatives. However, the structure of the former is very likely to be 307. With dimethylamine in benzene (25°, 5 min), ethyleneimine in ether (25°, 3 min), and alcoholic ammonia (25°, few min), this dichloro derivative was assumed to form 3-amino derivatives. The high reactivity of as-triazines is demonstrated by the facile ethoxylation... 

The 3-amino-8-oxo derivative of 1,2,4,5,7-pentaazanaphthalene (475) is known as well as various 3-substituted derivatives of the 6,8-dioxo compound. The 3-methylthio- and 3-ethylthio-6,8-dioxo derivatives and their 7-methyl and 5,7-dimethyl analogs were prepared by ring-closure. 3-Ethylthiopyrimido[4,5-e]-as-triazine-6,8-dione was 3-substituted with alkali 2N, 100°, > 30 min) or acid 2N, 100°, < 2 hr, 70% yield) and with ammonia, aniline, piperidine, or monoalkylamines (in pyridine, 115°, 4 hr, 75-85% yield). ... 

The halogenation of 3-methoxy- or 3-methyl(dimethyl)amino-1,2,4-triazine 2-oxides 18 was found to proceed in a similar manner, resulting in 6-halo-1,2,4-triazine 2-oxides 19 (77JOC3498, 78JOC2514). 

The reaction of 3-amino-1,2,4-triazine 1-oxide 1 with methyl iodide in the presence of sodium bicarbonate leads to the methylation of the amino group to afford 3-methylamino-l,2,4-tiiazine 1-oxide 123. This iV-oxide 123, under neutral conditions in the presence of Mel, undergoes methyl group migration to the N(2) atom of the 1,2,4-triazine ring, yielding 3-imino-2-methyl-1,2,4-triazine 1-oxide 124. The same product 124 was obtained by direct methylation of compound 1 under neutral conditions (84TL1677). 

When 5-methylthiosemicarbazide is used instead of amidrazone, 3-amino-1,2,4-triazine 4-oxides can be obtained. In this way 3-amino-5-methyl-6-phenyl-1,2,4-triazine 4-oxide 138 was synthesized from isonitrosopropiophenone [52CIL907, 89IJC(B)556]. 

Chemical Name Sodium salt of (6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(methoxyimino)ace-tamido] -8-oxo-3-[[(1,4,5,6-tetrahydro-4-methyl-5,6-dioxo-as-triazin-3-yl)thio] methyl] -5-thia-1 -azabicycio [4.2.0] oct-2-ane-2-carboxylic acid... 

The synthesis of 987 from 985 via 986 has been reported (83S759) by reaction of 985 with aryl isothiocyanates under neutral conditions. The reaction of 4-amino-6-anilino[l,2,4]triazine 988 with methyl iodide and then carbon disulfide gave 989 (90MI3, 90MI9). 

CN [6/ -[6ct.7p(Z)]]-7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyI]aniino]-8-oxo-3-[[(l,2,5,6-tetrah)/dro-2-mcthyl-5,6-dioxo-l,2,4-triazin-3-yl)thio]methyl]-5-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid... 

C7H22N2 140-80-7) see Chloroquinc Mepacnne 7(77)-amino-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-l,2,4-triazin-3-yl)thio]mcthyl]-3-cephem-4-carboxylicadd (C12H13N5O5S2 58909-56-1) see Ceftriaxone (15-franx)-l-amino-2,3-dihydro-l//-inden-2-ol (CyH NO 163061-74-3) see Indinavir sulfiite cis-l-amino-2,3-dihydro-l//-inden-2-ol (C9H11NO 7480-35-5) see Indinavir sulfate... 

Compound 7-ethyl-7-methyl-3-phenyl-2,3,4,9-tetrahydropyrimido[l,2-tf][l,3,5]triazine-6,8-dione 71 <2002JHC663> was prepared by the one-pot condensation reaction of 6-amino-3-cthyl-3-mcthyl-5//-pyndinc-2,4-dionc 70 with aromatic amines and formaldehyde (Equation 3). 

Most of the reported triazinothiadiazines have been prepared from 1,2,4-triazine derivatives. Treatment of amino-1,2,4-triazine 28 with chloroacetyl chloride in dioxane in the presence of triethylamine at 10 °C resulted in the formation of 6-methyl-4-(A -chloroacetamido)-3-thioxo-5-oxo-2,3,4,5-tetrahydro-l,2,4-triazine 29 and 3-methyl-4,7-dioxo-4,6,7,8-tetrahydro-l,2,4-triazino[3,4-A][l,3,4]thiadiazine 15 (Scheme 1) <2005JHC935>. 

Substituted aminotriazinones have proved to be important synthons in heterocyclic syntheses. 4-Amino-6-methyl-3-mercapto-[l,2,4]triazin-5-one 32 reacted with bromomalononitrile in the presence of sodium hydroxide to afford the... 

Chiral 4-(l -arylpropyl)amino-3-mercapto-6-methyl-4//-1,2,4-triazin-5-ones were... 

The electrochemical oxidation of catechols in the presence of 6-methyl-1,2,4-triazin-3-thion-5-one and 4-amino-6-methyl-l,2,4-triazin-3-thion-5-one as nucleophiles in aqueous solutions provided an efficient electrosynthesis of thiazolo[3,2-6][l,2,4]triazin-7-one and l,2,4-triazino[3,4-/)J 1,3,4-thiadiazinc derivatives respectively <06TL1713> <06TL8553>. 

Methylthiopyrido[2,3-e][ 1,2,4]triazine 41 was prepared (76KGSI140) by cyclization of 2-amino-3-hydrazinopyridine 40 with carbon disulfide followed by methylation. Oxidation of 41 with chlorine afforded the 3-methylsulfonopyridotriazine 42. Heating 41 with morpholine or pyrrolidine gave 43, whereas the reaction at 20°C gave 44. 

The ring system in 541 was synthesized (76JHC1249) by interaction of 4-hydrazino-7-phenylpyrazolo[l,5-a][l,3,5]triazine 540 and ethyl pyruvate. The hydrazino derivative 540 was prepared on cyclocondensation of 5-amino-l-thioamido-3-phenylpyrazole 537 with triethyl ortho-formate to give the pyrazolotriazinethione 538 followed by methylation to give 539 and hydrazinolysis to give 540. 

Substituted derivatives of l-(tetrahydrobenzo[b]thiophen-2-yl-3-carboxylate)-5-phenyl-6-thio-l,2,4-triazin-4-one have been synthesized by heterocyclization reactions of different hydrazones obtained from 2-amino-tetrahydrobenzo[b]thiophene-3-carboxylate with phenyl isothiocyanate <00PS275>. Reaction of 5-methyl isothiosemicarbazide with a-amino acid vicinal tricarbonyl reactive substrates 1 and 2 yields 1,2,4-triazine substituted a-amino acids, as an equimolar mixture of regioisomers 3a/3b and 4a /4b, respectively <00JCS(P1)299>. 

Cotterill [100] studied the effect of ammonium nitrate fertilizer on the electron capture or nitrogen specific gas chromatographic determination of Triazine plus other types of herbicide (Atrazine(2-chloro-4-ethylamino-6-isopropylamino, 1,3,5 triazine), Simazine (2-chloro-4.6 bis ethyl amino 1,3,5 triazine), Linuron (3,4,-chlorophenyl-l-methoxy-l-methyl urea), Metribuzin, Triallate and Phorate) residues in soil. 

Acetamido-4-amino-6-chloro-s-triazine, see Atrazine Acetanilide, see Aniline, Chlorobenzene, Vinclozolin Acetic acid, see Acenaphthene, Acetaldehyde, Acetic anhydride. Acetone, Acetonitrile, Acrolein, Acrylonitrile, Aldicarb. Amyl acetate, sec-Amyl acetate, Bis(2-ethylhexyl) phthalate. Butyl acetate, sec-Butyl acetate, ferf-Butyl acetate, 2-Chlorophenol, Diazinon. 2,4-Dimethylphenol, 2,4-Dinitrophenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Esfenvalerate. Ethyl acetate, Flucvthrinate. Formic acid, sec-Hexyl acetate. Isopropyl acetate, Isoamyl acetate. Isobutyl acetate, Methanol. Methyl acetate. 2-Methvl-2-butene. Methyl ferf-butvl ether. Methyl cellosolve acetate. 2-Methvlphenol. Methomvl. 4-Nitrophenol, Pentachlorophenol, Phenol. Propyl acetate. 1,1,1-Trichloroethane, Vinyl acetate. Vinyl chloride Acetoacetic acid, see Mevinphos Acetone, see Acrolein. Acrylonitrile. Atrazine. Butane. 

CyclohexyT6-amino-l -methyl-s-triazine-2,4(l//,3/4dione, see Hexazinone... 

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