RU2010126143A - METHOD FOR PRODUCING 5-SUBSTITUTED 1-H-1,2,4-TRIAZOL-3-CARBONIC ACIDS AND THEIR DERIVATIVES - Google Patents
METHOD FOR PRODUCING 5-SUBSTITUTED 1-H-1,2,4-TRIAZOL-3-CARBONIC ACIDS AND THEIR DERIVATIVES Download PDFInfo
- Publication number
- RU2010126143A RU2010126143A RU2010126143/04A RU2010126143A RU2010126143A RU 2010126143 A RU2010126143 A RU 2010126143A RU 2010126143/04 A RU2010126143/04 A RU 2010126143/04A RU 2010126143 A RU2010126143 A RU 2010126143A RU 2010126143 A RU2010126143 A RU 2010126143A
- Authority
- RU
- Russia
- Prior art keywords
- substituted
- hydrazide
- key intermediate
- triazole
- organic solvents
- Prior art date
Links
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1. Способ получения 5-замещенных 1-Н-1,2,4-триазол-3-карбоновых кислот и их производных, включающий синтез ключевого интермедиата - гидразида замещенной формимидной кислоты в среде диэтилового эфира, его последующее ацилирование ангидридами или хлорангидридами карбоновых кислот в присутствии или отсутствии основания, циклизацию ацилированного производного в производное 5-замещенной 1-Н-1,2,4-триазол-3-карбоновой кислоты, отличающийся тем, что ключевым интермедиатом является гидразид 1-бензилоксикарбонилформимидной кислоты, синтезируемый из 1 экв. бензилцианформата и 1-1,5 экв. безводного гидразина, а термическую циклизацию N-ацилированного гидразида 1-бензилоксикарбонилформимидной кислоты проводят в отсутствии растворителя при температуре 120-160°С, с последующей кристаллизацией полученных бензиловых эфиров 5-замещенных 1-Н-1,2,4-триазол-3-карбоновых кислот из спиртов и водно-спиртовых смесей или органических растворителей. ! 2. Способ по п.1, отличающийся тем, что в качестве органических растворителей при синтезе ключевого интермедиата используют диоксан, тетрагидрофуран, бензол, толуол, хлороформ, дихлорметан, петролейный эфир, гексан. ! 3. Способ по п.2, отличающийся тем, что в качестве ацилирующих агентов используют смешанные ангидриды, ацилазиды, гетероциклические производные, в том числе имидазолиды и бензотриазолиды, сложные эфиры, в том числе метиловые, этиловые ариловые, гетероариловые, O-ацилмочевины. ! 4. Способ по п.3, отличающийся тем, что в качестве основания при ацилировании используют третичные амины, в том числе гетероциклические, алкоголяты и гидриды щелочных металлов, оксиды и гидроксиды щелочных и щело 1. The method of obtaining 5-substituted 1-H-1,2,4-triazole-3-carboxylic acids and their derivatives, including the synthesis of a key intermediate - substituted hydrazide hydrazide in diethyl ether, its subsequent acylation with anhydrides or carboxylic acid chlorides in the presence or absence of a base, cyclization of the acylated derivative to a 5-substituted 1-H-1,2,4-triazole-3-carboxylic acid derivative, characterized in that the key intermediate is 1-benzyloxycarbonylformimide acid hydrazide synthesized from 1 eq. benzyl cyanformate and 1-1.5 equiv. anhydrous hydrazine, and the thermal cyclization of the N-acylated hydrazide of 1-benzyloxycarbonylformimide acid is carried out in the absence of solvent at a temperature of 120-160 ° C, followed by crystallization of the obtained 5-substituted 1-H-1,2,4-triazole-3-carboxylic benzyl esters acids from alcohols and water-alcohol mixtures or organic solvents. ! 2. The method according to claim 1, characterized in that dioxane, tetrahydrofuran, benzene, toluene, chloroform, dichloromethane, petroleum ether, hexane are used as organic solvents in the synthesis of the key intermediate. ! 3. The method according to claim 2, characterized in that mixed anhydrides, acyl azides, heterocyclic derivatives, including imidazolides and benzotriazolides, esters, including methyl, ethyl aryl, heteroaryl, O-acylureas, are used as acylating agents. ! 4. The method according to claim 3, characterized in that tertiary amines, including heterocyclic, alkoxides and hydrides of alkali metals, oxides and hydroxides of alkali and alkali, are used as the base for acylation
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RU2010126143/04A RU2446163C2 (en) | 2010-06-28 | 2010-06-28 | Method of producing 5-substituted 1-h-1,2,4-triazole-3-carboxylic acids and derivatives thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RU2010126143/04A RU2446163C2 (en) | 2010-06-28 | 2010-06-28 | Method of producing 5-substituted 1-h-1,2,4-triazole-3-carboxylic acids and derivatives thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2010126143A true RU2010126143A (en) | 2012-01-10 |
RU2446163C2 RU2446163C2 (en) | 2012-03-27 |
Family
ID=45783259
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2010126143/04A RU2446163C2 (en) | 2010-06-28 | 2010-06-28 | Method of producing 5-substituted 1-h-1,2,4-triazole-3-carboxylic acids and derivatives thereof |
Country Status (1)
Country | Link |
---|---|
RU (1) | RU2446163C2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2605414C1 (en) * | 2015-11-10 | 2016-12-20 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский технологический университет" | Method of producing 5-substituted 1,2,4-triazole-3-carboxylic acids and derivatives thereof from universal precursor |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3004060A (en) * | 1959-03-02 | 1961-10-10 | American Cyanamid Co | 1-cyanoformimidic acid hydrazide |
JPS59199681A (en) * | 1983-04-26 | 1984-11-12 | Ube Ind Ltd | Production of 1,2,4-triazole-3-carboxamide |
-
2010
- 2010-06-28 RU RU2010126143/04A patent/RU2446163C2/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
RU2446163C2 (en) | 2012-03-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Zeng et al. | Silver-catalyzed decarboxylative acylation of quinoxalin-2 (1 H)-ones with α-oxo-carboxylic acids | |
ES2437751T3 (en) | Procedures for synthesizing 3- (substituted dihydroisoindolinone-2-yl) -2,6-dioxopiperidine and intermediates thereof | |
ES2587738T3 (en) | Quinoxaline and quinoline derivatives as kinase inhibitors | |
RU2015106856A (en) | METHOD FOR PRODUCING PYRAZOLECARBOXYLIC ACID DERIVATIVES | |
RU2014153136A (en) | METHODS FOR PRODUCING SOME 2- (PIRIDIN-3-IL) THIAZOLES | |
IL262055A (en) | Synthesis of lactams | |
JP2021042230A5 (en) | ||
DK2748157T3 (en) | PROCEDURE FOR THE PREPARATION OF TETRAZOLE SUBSTITUTED ANTHRANILY ACID DIAMIDE DERIVATIVES BY USING BENZOXAZINONES WITH AMINES | |
JP6523334B2 (en) | Method for the preparation of substituted cycloserines | |
RU2016120007A (en) | METHODS AND INTERMEDIATE COMPOUNDS FOR PRODUCING A MACROCYCLIC INHIBITOR OF HEPATITIS C VIRUS PROTEASE | |
Cui et al. | A novel one-pot synthesis of α-keto-1, 3, 4-oxadiazole derivatives based on isocyanide-Nef reaction | |
Sharma et al. | Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1, 4-thiazine heterosystem | |
Hadjeri et al. | Alkylation of 2-phenyl-4-quinolones: Synthetic and structural studies | |
Pace et al. | Highly efficient and environmentally benign preparation of Weinreb amides in the biphasic system 2-MeTHF/water | |
Su et al. | An efficient one‐pot synthesis of N‐(1, 3‐diphenyl‐1H‐pyrazol‐5‐yl) amides | |
Obydennov et al. | Bio-based triacetic acid lactone in the synthesis of azaheterocycles via a ring-opening transformation | |
Lu et al. | One pot synthesis of pyrrolo [3, 4-c] quinolinone/pyrrolo [3, 4-c] quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC) | |
RU2010126143A (en) | METHOD FOR PRODUCING 5-SUBSTITUTED 1-H-1,2,4-TRIAZOL-3-CARBONIC ACIDS AND THEIR DERIVATIVES | |
Wu et al. | Highly efficient and diastereoselective construction of bispirooxindoles through a cascade Michael-cyclization reaction | |
CN105980360B (en) | The manufacturing method of 2- acyl imine pyridine derivate | |
Mulwad et al. | Synthesis and antibacterial screening of N-[coumarin-6-yl] spiro-indoloazetidin-2-ones/thiazolidin-4-ones | |
Gao et al. | First synthesis of 2-tropolonylquinoline-4-carboxylic acid derivatives via Pfitzinger reaction in water | |
Sweis et al. | 2-(4-Carbonylphenyl) benzoxazole inhibitors of CETP: Scaffold design and advancement in HDLc-raising efficacy | |
Xi et al. | Regio-controlled synthesis of N-substituted imidazoles | |
NO20085033L (en) | Ruthenium II compounds |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20160629 |