Benzotri azines

The treatment of 3-amino-1,2,4-triazine 2-oxides 1 or 3-amino-1,2,4-benzotri-azine 1-oxides 29 with nitrous acid proceeds as a diazotization reaction, but the diazo compounds have never been isolated owing to the easy displacement of the di-azo group with nucleophiles. Thus the reaction of 3-amino-1,2,4-triazine 2-oxides 1 with sodium nitrite in hydrochloric or hydrobromic acids leads to the corresponding 3-halogen-1,2,4-tiiazine 2-oxides 119 or 3-bromo-l,2,4-benzotriazine 1-oxides 120 (77JOC546, 82JOC3886). 

Benz, benz-, benzo- (preferably the latter before consonants as, Benztriazin, benzotri-azine). arsinigsaure, /. benzarsinous acid, arsinaaure, /. benzarsinic (benzarsonic) acid. 

Daniels JS, Gates KS (1996) DNA cleavage by the antitumor agent 3-amino-1,22,4-benzotri-azine 1,4-dioxide (SR4233) evidence for involvement of hydroxyl radical. J Am Chem Soc 118 3380-3385... 

Mass spectra of 4-anilino-l,2,3-benzotriazines 27 and the isomeric 3-aryl-l,2,3-benzotri-azin-4-imines 28, as well as of the 2-alkyl-4-(arylimino)-1,2,3-benzotriazinium betaines 32, have been studied intensively.101 The fragmentation of 27 and 28 starts with the loss of nitrogen, while for 32 the loss of an or/ho-substituent in the aryl group or the elimination of KN2 is... 

Reaction of 2-ureidobenzamide (10, isatoic diamide) with nitrous acid yielded 1,2,3-benzotri-azin-4(3//)-one (11).7,8... 

With diphenylcyclopropenone 17,1,2,3-benzotriazines 16 gave one, two or three of the following cycloadducts pyrazolo[l,2- ][l,2,3]benzotriazin-1-ones 18, pyrazolo[l,2- ][l,2,3]benzotri-azin-3-ones 19, or pyrazolo[2,3- ]quinazolin-3-ones 20. The latter products require rearrangement of a [3 + 2] cycloadduct resulting from addition of the 1,2,3-benzotriazine to the 2,3-bond of 17.292... 

Few examples of the formation of 1,2,4-triazines by the combination of an N4-C5-C6-N1 fragment with the N2-C3 fragment have been published, and all of them arc 1,2,4-benzotri-azine syntheses. 2-Nitroaniline reacts with cyanamides to give 2-(2-nitrophenyl)guanidines which cyclizc under basic conditions to l,2,4-benzotriazin-3-amine 1-oxides. 133a d... 

Flash-vacuum pyrolysis of a-benzotriazolyl-/ -oxO tributylphosphorus ylides results in extrusion of tributylphosphane to give 3-acetyl-1,2,4-benzotriazine (9) and 2-acetylbenzonitrile. The formation of these products is explained by the initial formation of acetyl(benzotri-azolyl)carbene which either forms 3-acetyl-l,2,4-benzotriazine (9) or 4-acetyl-l,2,3-benzotri-azine. Elimination of nitrogen from the 1,2,3-benzotriazine and 1,3-acetyl migration affords the isolated 2-acetylbenzonitrile.211... 

Oxidation of 1,2,4-benzotriazine with hydrogen peroxide in acetic acid yields 1,2,4-benzotri-azine 1-oxide (11) and benzotriazole. In contrast, oxidation with 3-chloroperoxybenzoic acid affords 1-oxide 11 (12%) and 1,2,4-benzotriazine 2-oxide (5%).243... 

Diethoxyphosphoryloxy-l,2,3-benzotri-azin-4(3Hj-one (DEPBT), an effective coupling agent for the synthesis of linear and cyclic peptides, both in solution and on solid support. Beside its remarkable resistance to racemization in peptide bond formation, it is not necessary to protect the... 

Azido-4-isopropylamino-6-methylthio-1,3,5-triazine. SeeAziprotryn Azimethylene. See Diazomethane Azimidobenzene Aziminobenzene. See 1H-Benzotri azole Azine. See Pyridine Azinphos-ethyl CAS 2642-71-9... 

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