DIRECT INTRODUCTION OF HETEROCYCLIC RESIDUES INTO 1,2,4-TRIAZIN-5(2H)ONES

摘要

3-Aryl-1,2,4-triazin-5(2H)-ones la-e react with indoles 2a-c in trifluoroacetic acid/chloroform or in boiling butanol or acetic acid to give 3-aryl-6-(indolyl-3)-1,6-dihydro-1,2,4-triazin-5(2H)-ones 3a-g. Oxidation of the dihydro-1,2,4-triazin-5(2H)-ones 3a-e afforded 6-(indolyl-3)-1,2,4-triazin-5(2H)-ones 4a-e, products of nucleophilic substitution of hydrogen in la-e Refluxing Ib with N-methylpyrrole 5b in butanol for an extended time resulted in the formation of 3-(4-chlorophenyl)-6-(1-methylpyrrolyl-2)-1,2,4-triazin-5(2H)-one 4h. The reaction of lac with indoles 2a-c, pyrroles 5a,b, 1,3-dimethyl-2-phenylpyrazol-4-one (8) and aminothiazoles 9a,b in acetic anhydride affords the 1-acetyl-3-aryl-6-aryl-6-hetaryl-1,6-dihydro-1,2,4-triazin-5(2H)-ones 6a-s. Reaction of la-e with N-methylpyrrole 5b in acetic anhydride gives beside the 1:1 addition products 6h-k also the 2: 1 addition products 7a-c. [References: 11]