PROCESS FOR PREPARING 6-ARYL-4H-S-TRIAZOLO[3,4-c]-THIENO[2,3-e]-1,4-DIAZEPINES

Abstract

An improved process for preparing 6-aryl-4H-s-triazolo[3,4-c]-thieno[2,3-e]-1,4-diazepines of formula I, wherein: R 1 is a hydrogen or halogen atom or a C 1 -C 6 alkyl group, R 2 is a hydrogen or halogen atom or a C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, C 3 -C 6 cycloalkyl group or a 5- or 6-membered oxygen-, sulphur- or nitrogen-containing heterocyclic group which may optionally be substituted at the nitrogen atom by a C 1 -C 3 alkyl group, and R 3 is a hydrogen or halogen atom.

1 . A process for preparing a 6-aryl-4H-s-triazolo[3,4-c]-thieno[2,3-e]-1,4-diazepine of the formula I,  
       
         
           
           
               
               
           
         
         wherein  
         R 1  denotes a hydrogen or halogen atom or a C 1 -C 6  alkyl group,  
         R 2  denotes a hydrogen or halogen atom or a C 1 -C 6  alkyl, C 1 -C 6  hydroxyalkyl, C 3 -C 6  cycloalkyl group or a 5- or 6-membered oxygen-, sulphur- or nitrogen-containing heterocyclic group which may optionally be substituted at the nitrogen atom by a C 1 -C 3  alkyl group, and  
         R 3  denotes a hydrogen or halogen atom,  
         in which process,  
         a 5-aryl-2-chlorothieno[2,3-e]-1,4-diazepine of the formula III  
         
           
             
             
                 
                 
             
           
         
         wherein R 1  and R 3  are as herein defined,  
         is reacted with an acylhydrazine of the formula IV  
           R2—CO—NH—NH2  (IV)  
         wherein R 2  is as hereinbefore defined.  
       
     
     
         2 . The process according to claim  12 , wherein R 1  denotes a bromine atom, R 2  denotes a methyl group, and R 3  denotes a chlorine atom.  
     
     
         3 . The process according to claim  12 , wherein the compound of the formula (III) is reacted with acetic acid hydrazide at a temperature below 100° C. in the presence of an inert diluent.