Reactivity of methyl (3,6-dichloropyridazin-4-yl)acetate towards nucleophiles

Methyl (3,6-dichloropyridazin-4-yl)acetate (II), prepared from methyl (3,6-dihydroxypyrid-azin-4-yl)aeetate (1) by chlurination with phosphorus oxychloride, was used for studies of nucleo-philic displacement reactions and it has been found that only the chlorine atom at position 6 was displaced with hydrazine. With diluted hydrochloric acid both chlorine atoms were displaced with the 6-oxo isomer predominating. By turning the aromatic ring of pyridazine into an o-quinoid system, the chlorine atom at position 3 became mobile. Cyelization of (6-hydrazino-s-triazolo-4,3-b ]pyridazin-7-yl)acetic acid hydrazide (XIX) gave 6-aminopyrrolo3,2-e ]s-triazlo 4,3-b ]-pyridazm-7(8H)one (XXI).