Beta - (substituted-hydrazino) - alpha - cyano acrylic acids and derivatives,and process for preparing n-substituted pyrazoles

Abstract

Abstract PROCESS OF REACTING MONO-SUBSTITUTED HYDRAZINES WITH A-CYANO-A-FORMYL-ACETIC ACID ESTERS OR THEIR REACTIVE ALDEHYDE DERIVATIVES, SUCH AS ENOL ETHERS, ACETALS OR MERCAPTALS AND QUITE GENERALLY WITH A-CYANO-A-FORMYL-ACETIC ACID OR ITS ACID DERIVATIVES, OR THE REACTIVE ALDEHYDE DERIVATIVES THEREOF SUCH AS ARE MENTIONED ABOVE. ACID DERIVATIVES TO BE USED ARE PIMARILY THOSE WHICH CONTAIN AN OXO, THIOKETO, OR IMINO GROUP, SUCH AS ESTERS, AMIDES OR AMIDINES BUT ALSO OTHER DERIVATIVES MAY BE USED, SUCH AS THE NITRILE. ESTERS ARE PREFERABLY THOSE OF ALKANOLS, SUCH AS LOWER ALKANOLS, E.G.METHANOL, ETHANOL, PROPANOL OR BUTANOL. ALSO PRODUCTS HAVING THE FORMULAE 1-R'',4-R,5-(H2N-)PYRAZOLE OR 2-R'',4-R,5-(H2N-)-3H-PYRAZOLE WHEREIN R STANDS FOR A CARBOXYL GROUP OR A DERIVATIVE THEREOF AND R'' FOR THE SUBSTITUENT OF THE HYDRAZINE USED FOR THE REACTION SUCH AS AN ALKYL, OXAALKYL, HYDROXYALKYL, CYCLOALKYL, ARYL OR HETEROCYCLIC RADICAL, USEFUL AS INTERMEDIATES FOR PREPARING A VARIETY OF PYRAZOLO-PYRIMIDINES. THE INVENTION ALSO INCLUDES, AS INTERMEDIATES FOR THE PYRAZOLES, B-(N1-R-N2-R"-HYDRAZINO)-A-CYANO-ACRYLIC ACID, ITS LOWER ALKYL ESTERS, AMIDE, THIOAMIDE, AMIDINE AND NITRILE IN WHICH R REPRESENTS A MEMBER OF THE GROUP CONSISTING OF LOWER ALKYL, CYCLOALKYL, LOWER MONO-HYDROXYALKYL, LOWER ALKOXY ALKYL, PHENYL, HALOPHENYL, LOWER ALKYLPHENYL, NITROPHENYL AND PYRIDYL, SAID CYCLOALKYL HAVING FROM 5 TO 6 CARBON ATOMS AND R" REPRESENTS A MEMBER SELECTED FROM THE GROUP CONSISTING OF LOWER ALKANOYL AND ARYLIDENE.

Inventors

• 👤 Jean Druey
• 👤 Paul Schmidt

Bibliographic Details