Addition reactions of heterocycles. VI. Reactions of 1,2‐dimethylpyrrole and 1‐methyl‐2‐carbomethoxypyrrole with nitrilimines

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Abstract
Addition reactions of 1,2‐dimethylpyrrole and 1‐methyl‐2‐carbomethoxypyrrole with C‐acetyl‐N‐phenylnitrilimine, have been investigated. 1,2‐Dimethylpyrrole gives three different types of adducts: i.e. bis‐cycloadducts (Vc) and (VIc), spirocycloadduct (IX), and non cyclic bis‐adduct (XII). On the other hand, 1‐methyl‐2‐carbomethoxypyrrole gives the bis‐cycloadduct (VIb) only. Compound XII arises probably through a double 1,3‐addition reaction, whereas the formation of cycloadducts Vc, VIc, and IX depends on the substituents present at C2 of the pyrrole ring and consequentially on the intermediary occurence of mono‐cycloadduct (IIIc), its methylenic tautomer VII, VIc, and XL The behaviour of the cycloadducts towards heating or acidic treatment showed a termal cleavage of the pyrazoline ring and acidic cleavage of the pyrrolidine ring.

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