10-Amino-2,4-dioxo-2,3,4,10-tetrahydro

Figure 4.9 Structures of selected SARMs androgen receptor antagonists bicalutamide (1) and flutamide (2) arylpropionamide-based agonists S-1 (3), S-4 (Andarine, 4),S-22 (5) bicyclic hydantoin-derived antagonist nilutamide (6) agonists BMS-564929 (7), and 4-(7-hydroxy-l,3-dioxo-tetrahydro-pyrroIo[l,2-c]imidazoI-2-yI)-naphthaIene-l-carbo-nitrile (8) quinolinone-based SARMs LG-121071 (9), LGD-2226 (10), and bisethyl-amino-4-trifluoromethyIquinoIin-2(lH)-one (11) and tetrahydroquinoline-derived SARMs S-40503 (12), and 2-methyI-2-(8-nitro-3a,4,5,9b-tetrahydro-3H-cycIopenta[c] chinoIin-4-yI)propan-l-oI (13).

Glutamic acid, p-aminobenzoyl-2-amino-8-methyl-4,9-dioxo-6,7,8,9-tetrahydro-4H-pyrazino[l,2-u][l,3,5]tria2in-7-ylmethyl ester, 3, 308... 

Purine, 2-amino-6,8-dioxo-I,6,7,8-tetrahydro-reactions, 5, 557 Purine, 6-amino-2-fluoro-synthesis, S, 597 Purine, 2-amino-9-methyI-sulfonylation, 5, 551 Purine, 6-amino-2-methyIthio-hydrolysis, 5, 560... 

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... 

RN 59989-20-7 MF C.jH,oN40, CsH,>,NO MW 367.45 EINECS 262-012-4 CN 1,2,3,6-tetrahydro-l, 3-dimethyl-2,6-dioxo-7ff-purine-7-acetic acid compd. with 6-amino-2-methyl-2-heptaminol (1 1)... 

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>. 

The 2,3-dioxo-6-thioxo-2,3,5,6-tetrahydro-l/7-imidazo[l,2-A]pyrazole 393 and 5,6-dioxo-2,3-dihydro-l//-imidazo[l,2- ]-imidazole 395 were synthesized by condensation of the respective 5-amino-3-thioxo-2,3-dihydro-pyrazole 392 and 2-aminoimidazoline 394 compounds with either oxalyl dichloride or diethyl oxalate in moderate to poor yields (Equations 178 and 179) <1995JPR472, 2002EJM845>. These cyclizations can suffer from various side reactions such as expulsion of CO, polymerization, or formation of open-chain products. To solve these problems, reagents such as oxalic acid bis-imidoyl- and bis-hydrazoylchlorides 397 and 400 as well as 2,3-dichloroquinoxalines 403... 

Hydrazination of 4-aryl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazine (66) also affords a rearranged product, 4-amino-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (81JHC953). This replacement of the A-aryl group by the N-amino group requires the intermediacy of the ring-opened compound 67. This intermediate could be isolated under mild conditions and its structure was proven by an independent synthesis. From this structure it can be concluded unequivocally that the ring transformation involves initial addition of the hydrazine at C-5 and not at C-3 (Scheme III.37). 

Ceftriaxone Ceftriaxone, 7-[[(2-amino-4-lhiazolyl)-2-(Z)-(methyoximino)acetyl]amino]-8-oxo-3-[[(l,2,5,6-tetrahydro-2-methyl-5,6-dioxo-l,2,4-triazin-3-yl)thio]methyl]-5-thia-l-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.72), is synthesized by acylating 7-amino-3-[[(2,5-dihydro-6-hydroxy-2-methyl-l,2,4-triazin-5-on-3-yl)thio]methyl]3-cefem-... 

Amino-benzimidazole addieren 1 mol Isocyanat bei 20° am ewrfocyclischen, beim Erwarmen am exocyclischen N-Atom, mit weiterem Isocyanat cyclisiert das Addukt zu 2,4-Dioxo-l,2,3,4-tetrahydro-5-triazino-[l,2-a]benzimidazolen). Die Umsetzung ist ein-oder zweistufig durchfuhrbar450 z. B. ... 

Disubstituierte 5-Brom-6-methyl-2,4-dioxo-l, 2,3,4-tetrahydro-pyrimidine rcagieren mit aliphatischen Aminen in Dimethylformamid unter Ersatz des Brom-Atoms durch eine Amino-Gruppe4. Dagegen erfolgt bei Reaktion mit aromatischen Aminen allylische Substitution durch eine Arylamino-Gruppe, und man erhalt z.B. 6-Anilino-1,3-dimethyl-... 

Amino acids and phosgene were used, as previously reported,1 for the preparation of 2,6-dioxo derivatives.114 Reaction of dialkylmalonyl chloride with A-methylisobutyramide to yield 27 [Eq. (17)] is a general method of forming 4,6-dioxo derivatives of tetrahydro-1,3-oxazine, as reported by Martin et al.115... 

Dioxo-6,7,8,9-tetrahydro-4//-pyrido[l, 2-a]pyrimidines 35 exhibit an oxo-enol tautomerism, which was studied by UV, IR, and NMR methods (85JHC1253). In the solid phase enol tautomers are present, while in a polar solvent an electron withdrawing substituent at position 3 shifts the equilibrium toward the enol form. The analogous 9-amino derivatives exist exclusively as 9-amino-6,7-dihydropyrido[l,2-a]pyrimidin-4-ones. 

Pyridinamine (54) with diethyl ethoxymethylenemalonate gave ethyl 4-oxo-l,4-dihydro-l,5-naphthyridine-3-carboxylate (55) (reactants, Dowtherm A, 150°C, reflux, 1 h 80%) 101 somewhat similarly, 5-amino-2(l//)-pyridinone gave ethyl 4,6-dioxo-l,4,5,6-tetrahydro-l,5-naphthyridine-3-carboxylate (56) [Et0CH=C(C02Et)2, Ph20, reflux, 1 h 20%].233... 

Diethoxycarbonylvinyl)amino- l-methyl-2(l/f)-pyridinone (11) gave ethyl 7-methyl-4,8-dioxo-l,4,7,8-tetrahydro-l,7-naphthyridine-3-carboxylate (12) (Dowtherm A, reflux, N2, 25 min 83%).1116... 

Amino-1 -ethyl-4,7-dioxo-1,4,7,8-tetrahydro-1, 8-naphthyridine-3-carboxylic acid... 

Amino-2,7-dimethyl-3,8-dioxo-6-phenyl- 2,3,7,8-tetrahydro-2,7-naphthyridine- 4-carbonitrile >380 699, 1183... 

Reaction of 9-fluoro-8-isothiocyanato- and 8-iso(thio)cyanato-3,5, 6,7-tetrahydro-2//-pyrido[l,2,3-de]-l,4-benzoxazines with 2-amino-4,4-dimethylpyrroline, then with Br2, and with ethyl pipecolinate yielded 8-(6, 6-dimethyl-3,5,7,7-tetrahydropyrrolo[2,l-c][l,2,4]thiadiazol-3-ylidenamino)-9-fluoro and 8-(l,3-dioxo and l-oxo-3-thioxoperhydroimidazo[l,5-a]-pyridin-2-yl) derivatives, respectively (89EUP406993). Treatment of 9-fluoro-8-(2-hydroxymethylpiperidinothiocarbonylamino)-3,5,6,7-tetrahydro-2//-pyrido[l,2,3-de]-l,4-benzoxazine with HC1 gas in EtOH gave the 8-(perhy-dropyrrolo[l,2-c]thiazol-3-ylidenamino) derivative. 

Pyrimidin 6-Amino-5-brom-2,4-dioxo-1 -ethyl-1,2,3.4-tetrahydro-E15/2, 2213 (H->Br)... 

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