SU245554A1 - METHOD FOR PRODUCING TRIAZOLYLPYRAZOLES - Google Patents
METHOD FOR PRODUCING TRIAZOLYLPYRAZOLESInfo
- Publication number
- SU245554A1 SU245554A1 SU1240723A SU1240723A SU245554A1 SU 245554 A1 SU245554 A1 SU 245554A1 SU 1240723 A SU1240723 A SU 1240723A SU 1240723 A SU1240723 A SU 1240723A SU 245554 A1 SU245554 A1 SU 245554A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- triazolylpyrazoles
- producing
- substituted
- deamination
- followed
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000006481 deamination reaction Methods 0.000 description 3
- -1 3,5-dimethyl-substituted triazolylpyrazole Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QCBLZIBHRNBZEY-UHFFFAOYSA-N N1N=NC(C2=NNC=C2)=C1N Chemical class N1N=NC(C2=NNC=C2)=C1N QCBLZIBHRNBZEY-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HYXVVRJLDCYSLX-UHFFFAOYSA-N 2H-triazol-4-ylhydrazine Chemical compound NNC1=CN=NN1 HYXVVRJLDCYSLX-UHFFFAOYSA-N 0.000 description 1
- KTBVSTUQBSGBGI-UHFFFAOYSA-N 3-hydrazinyl-1,2,4-triazol-4-amine;dihydrochloride Chemical compound Cl.Cl.NNC1=NN=CN1N KTBVSTUQBSGBGI-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N Acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение относитс к области получени триазолилпиразолов общего строени The invention relates to the field of production of triazolylpyrazoles of general structure.
R IR i
N-N C C-R II II 1 I НС C-N NNCC-R II II 1 I HC C-N
/ NN/ Nn
I НI N
где R, R и R - водород, алкил, арил или аралкил, которые примен ют в качестве стабилизаторов фотографических эмульсий.where R, R and R are hydrogen, alkyl, aryl or aralkyl, which are used as stabilizers of photographic emulsions.
Известен способ получени соединений строени I конденсацией дигидрохлорида 3гидразино-4-амино-1 ,2,4-триазола с трехуглеродными компонентами, в качестве которых, например, примен ют ацетилацетон, с последующим дезаминированием образующихс 4-аминотриазолилпиразолов. По этому способу легко получают 3,5-диметилзамещенный триазолилпиразол. Однако получение триазолилпиразолов с иным замещением, например 4-замещенных, или содержащих только один заместитель (в 3- или 5-положении), вызывает известные затруднени , вследствие малой доступности трехуглеродных компонентов.A known method for the preparation of compounds of structure I by condensation of 3-hydrazino-4-amino-1, 2,4-triazole dihydrochloride with three-carbon components, for example, acetylacetone is used, followed by deamination of the resulting 4-aminotriazolylpyrazoles. By this method, a 3,5-dimethyl-substituted triazolylpyrazole is easily obtained. However, the preparation of triazolylpyrazoles with another substitution, for example 4-substituted, or containing only one substituent (in the 3- or 5-position), causes known difficulties, due to the low availability of the three carbon components.
Цель предлагаемого способа - синтез ранее неизвестных, например, 4-замещенных триазолилпиразолов, а также упрощение технологии процесса получени триазолилпиразолов .The purpose of the proposed method is the synthesis of previously unknown, for example, 4-substituted triazolylpyrazoles, as well as the simplification of the technology for producing triazolylpyrazoles.
По этому способу триазолилпиразолы общего строени I получают при конденсации гидразинаминотриазола с тетраалкоксипропанами общего строени In this method, triazolylpyrazoles of general structure I are obtained by the condensation of hydrazinotriazole with tetraalkoxypropanes of general structure
R R R OR R R R OR
C-CH-CC-CH-C
IIII
OROR
где R, R, R имеют те же значени , что и в формуле I, а R -алкил с последующим дезаминированием .where R, R, R have the same meanings as in formula I, and R is alkyl followed by deamination.
Реакцию провод т при рефлексировании исходных компонентов в этиловом спирте в присутствии сол ной кислоты с последующим дезаминированием без выделени 4-аминотриазолилпиразолов . Триазолилпиразолы формулы I получают с удовлетворительными выходами и в чистом состо нии.The reaction is carried out by reflexing the starting components in ethyl alcohol in the presence of hydrochloric acid, followed by deamination without isolation of 4-aminotriazolylpyrazoles. The triazolylpyrazoles of formula I are obtained in satisfactory yields and in pure condition.
По предлагаемому способу легко могут быть получены замещенные в 4-ом положении пиразольного остатка триазолилпиразоWith the proposed method, triazolylpyrazo substituted in the 4th position of the pyrazole residue can be easily obtained.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU245554A1 true SU245554A1 (en) |
Family
ID=
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4169838A (en) * | 1975-10-06 | 1979-10-02 | American Cyanamid Company | Pyrazolyltriazole herbicides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4169838A (en) * | 1975-10-06 | 1979-10-02 | American Cyanamid Company | Pyrazolyltriazole herbicides |
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