Interaction of 3,4-Dinitro-1-methylpyrrole with Secondary Amines: Alternative Formation of Pyrrolines or Cine Substitution Products

Article abstract of DOI:10.1021/jo00150a005

The course of the reaction of 1-methyl-3,4-dinitropyrrole with piperidine or morpholine in acetonitrile depends upon the reaction conditions.At refluxing temperature the main products are the cine substitution products, whereas at room temperature 2-pyrrolines are formed.Base-promoted decomposition of the latter yields products of formal direct denitration, whereas in the presence of Me3NH(1+) ion cine substitution products are obtained.