6533b7d3fe1ef96bd12612ef

RESEARCH PRODUCT

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

Nicolò VivonaGiuseppe CusmanoMichele Ruccia

subject

chemistry.chemical_compoundAddition reactionchemistryStereochemistryOrganic ChemistryPyrazolineRing (chemistry)Cleavage (embryo)Medicinal chemistryTautomerPyrrolidineAdductPyrrole

description

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.

yearjournalcountryeditionlanguage
1978-03-01Journal of Heterocyclic Chemistry
https://doi.org/10.1002/jhet.5570150222