Heterocyclic imines and amines. Part XIV. Products from 2,5-di-iminopyrrolidine (succinimidine) and hydrazine

Abstract

Hydrazine (in excess) reacts with 2,5-di-iminopyrrolidine (1) or succinonitrile to yield 6-hydrazino-3-hydrazono-2,3,4,5-tetrahydropyridazine (2). Treatment of this with acetone, glyoxylic acid, and butyl glyoxylate affords the expected di-condensation products; with glyoxal a polymeric hydrazone is obtained. Acylation of compound (2) with ethyl chloroformate was successful but attempts to oxidise the product to known pyridazines failed, as did attempts to dehydrogenate compound (2) to 3,6-dihydrazinopyridazine. 5-lmino-2-pyrrolidone (13) with hydrazine gave 6-hydrazino-4.5-dihydropyridazin-3(2H)-one (14).

In hot pyridine, succinonitrile reacts with an equimolar quantity of hydrazine to give a polymer, (C₄H₆N₄)_n; with 2 molecular proportions a dimeric condensation product, C₈H₁₆N₁₀, results. Structures for these are proposed on the basis of spectral and other evidence. The behaviour of these compounds and related pyridazines on thermolysis is reported.