SU577991A3 - Method of preparing 1,4-di-n-oxy-1,2,4-benztriazine - Google Patents

Description

one

A method for producing new 1,4,4-di-, N-i-1,2,4-benzthryazine derivatives, which can be used as bactericidal preparations, is proposed.

The literature describes a method for producing

derivatives of 1,4-di-N-oxide 1,2, .. triazine, based on the interaction of 3-ami 1-benzo-1,2,4-triazin-1,4-. dioxide with phosgene to form mono-N-oxide 5 0 sso-G, 2,4-oxadiazono 2,3-in ipi 13,4-sy .j, 2,4 - benztryazya, the latter with reac- tion. yay with methylamine in the environment of dimetyp formamide diets 1.4-d-C-methyluredura oxide. ..:, 2,4-benztriazina.

The use of the known ip i-reaction to substituted 1,2,4 benzene, benzotriaziums1 allowed us to obtain the previously described 1,4-cy-N-oxide-1,2,4-benztriazine derivatives, which have a bactericidal effect.

A method is proposed for the preparation of arbitrary 1,4-di-N-oxides 1,2,4 nsgr | 1az) (on the general formula arapkip or a heterocyclic residue, and if R and R are hydrogen, then another of these radicals can have all of these values except methyl; R and {, together with the adjacent nitrogen atom, mean morphopino, piperidine, and the pyrrologo group, which means that the compound of the general formula where X and Y have the indicated values is reacted with an amine of the general formula H - N (III) Br where R and T have the indicated meanings. Bleed by X and Y apkyl - or apkoxygr Upps preferably contain 1 to 4 carbon atoms. Substituents of the phenoxy group could be a C – C substituent, an alkoxy group containing 1–4 carbon atoms, or a halide. Denoted by R and R alkyl hydroxy or apkoxyapkyl groups contain 1–12 carbon atoms, preferably 1-6 carbon atoms, and having an apkoxy group with a vapic group, contains a maximum of 4 and preferably ymepoqa. R, representing arapkyl groups, are preferably a benzyl or phenethyl group, each of which in the phenyl ring can be mixed with lower alkyl, lower alkoxy, halogen, nitro,. lower haloalkyl, with Ipynnbi containing 1-4 carbon atoms as lower alkyl or lower alkoxy groups, fluorine, chlorine, bromine or iodine as a halogen and a trifluoromethyl group as a haloalkyl. 1 and R are a heterocyclic residue, mean pyridine, furan, thiophene, pyrrole or pyrimidine. Example. 1,4-di-N-3- (2, 4-dichlorobeneylureido) -7-methyl-1,2,4-benzotriazine oxide. 10 g (0.0456 mol) of mono-M-oxide 5-OXO-1,2,4-oxadiazllo-L2i3-B or 3.4 - 1,2,4-1-benztriazine are suspended in 2OO mltsioxan. 8.05 g (O, O456 mol) of 2,4-dichlorobenzylamine was added to this suspension at room temperature. A brown solid gradually precipitated from the purple solution obtained with the release of heat. The reaction mixture is stirred overnight at room temperature, sucked off, the precipitate is further washed with dioxane and heated with stirring for 5 minutes in 1OO ml of ethanol to 7O C. The hot suspension is sucked off and the residue is dried. The output of 12.9 g, so pl. 210-215 ° C. The compounds "listed in the table are prepared in a similar manner.

1,4-Di-H-oxide 3- (2-ethyl) pentyl ureid4-1,2,4. Brythriazone I

1,4-Di-N-oxide 3- {-dimethylamino) ethyl yreido-l, 2,4 benzgryaein

1,4-yi-lH-3- (-carboxymethyl) phenylureiao-7-methoxy-1, 2,4-benztriazine oxide

1,4-Di-bi-oxide 3- (3, 4-dichlorophenylpropylureido) -7-methyl-1,2,4-benzotriazine

1,4-Di-N-oxide of 3-benzylureido-1,2,4-benztriazina

1,4-Di-, N-oxide 3- (And-chlorophenylethylureido), 2,4-benztriazina

178-179

144-145

175

193-195

184-186

2O2-2O4

577991

1,4-AI-N-oxide 3-benzipureido-7-metip-1,2,4 benztriaaina

1,4-Di-N-3- (2,4-dichporphenippropipureido) 7-metip-1,2,4-benztriazine oxide

1,4-Di-N-oxide 3- (phenipropipureido) -1,2,4benegriayaina

1,4-Di-N-3- (ti -hporfenipetipureido) -7-metip-1, 2,4-benetriazine oxide

1,4-Di-N-3- (N, N-Diethypureido) Oxide - 1,2,4-benetria-aain

1,4-Di-N-OXIDE 3- (phenipetipureido) -1,2,4 benatriazhna

1,4-.DI-N-3- {pre-dacellate) -1,2,2-benztriazine

1,4-Di-N-oxide 3 - 2-ethyl-1,3-dioxypropip (2) ureido -1,2,4-benztriazina

1,4-Di-N-oxide 3- {heggigurus type) -1,2,4-benetriazine

1,4-Di-N-3- (carboxypentiaureido) -1,2,4 benztriazine oxide

1,4-Di-N-.oxide, 3-ureido-7-methoxy-1,2,4-benzgriazina

1,4-Di-N-oxide of Z-cyclopropnpureido-7-methoxy-1, 2,4-benztriazina

1,4-Di-N-oxide of Z-cycprohexipureido-7-methoxy-l, 2,4-benztriazina

1,4-Di-N-oxide of 3- (4-morpholinocarbonipamino) -7-methoxy-1, 2,4-benztriazina

1,4-Di-N-oxide 3- (2,6-dichporpenip9thylureido) 7-mtip-1, 2,4-benztriazina

D) Continuation of the table.

192-194

20О-202

168-171

212-214

12O-123

188-189

178-18О

152-154

188-189 192-194

218-22О

2.04-205

208-211

172-174

21 (V213