Synthesis of new heterocyclic compounds derived from 4-amino antipyrine

Abstract EN

In this work, isondoline -1,3-dione derivatives [2-5] were prepared from the corresponding anhydrides and 4-amino antipyrine [1].Derivatives [6-11] containing urea and thioureamoieties at position [4] were prepared from 4-amino antipyrine [1] and an appropriatearyl or alkyliso or (isothio) cyanates and then converted into pyrimidine derivatives [12-15].

Treatment of compound [1] with formic acid or acetic acid give the amide derivatives [16 and 17], which upon refluxing of compound [16]) with hydrazine hydrate in ethanol yielded the corresponding 2,3-dimethyl-1-phenyl-2,4-dihydro-1H-pyrazolo[4,3,e][1,2,4]-triazine [18].

Reacting compound [1] with acetyl acetone in boiling ethanol for 6hrs, leads to 4-amino antipyrine derivative [19].

The azomethines [20-22] were prepared from the corresponding aryl aldehydes and compound [1].