Condensed 1,2,4-Triazines, III

Article abstract of DOI:10.1002/ardp.19803130512

Alkylation of 3-mercaptophenanthreno<9,10-e>-1,2,4-triazine (1b) yielded the S-alkyl derivatives 2a-d.Amination of 1a afforded the 3-amino derivatives 3a-h.Reaction of 1a with hydrazine hydrate gave 3-hydrazinophenanthreno<9,10-e>-1,2,4-triazine (4) which underwent cyclisation with nitrous, formic or acetic acids giving the phenanthreno<9,10-e>-1,2,4-triazino<2,3-d>-1,2,3,4-tetrazole (5) and the phenanthreno<9,10-e>-1,2,4-triazino<2,3-d>-3H-methyl-1,2,4-triazoles 6, 7.Compound 4 also reacted with methyl cyanoacetate, ethyl acetoacetate, ethoxymethylenemalononitrile, ethyl ethoxymethylencyanoacetate or acetyl acetone to yield the 3-(pyrazol-1-yl)-phenanthreno<9,10-e>-1,2,4-triazines 8-12.