Polyfunctional nitriles in organic syntheses: a novel route to aminopyrroles, pyridazines and pyrazolo[3,4-c]pyridazines

Molecules. 2009 Feb 16;14(2):798-806. doi: 10.3390/molecules14020798.

Abstract

Phenacylmalononitrile 1 reacts with dimethylformamide dimethyl acetal to yield an enaminone which could be readily converted into a pyrrole or an aminopyridazine by treating with ammonium acetate and hydrazine hydrate, respectively. Compound 1 reacted with hydrazine hydrate in ethanol at room temperature to yield the dihydropyridazine 9 as a single product. In refluxing ethanol this product further reacted with hydrazine hydrate to yield the novel dihydropyrazolopyridazinamine 10.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Nitriles / chemistry*
  • Pyridazines* / chemical synthesis
  • Pyridazines* / chemistry
  • Pyrroles* / chemical synthesis
  • Pyrroles* / chemistry

Substances

  • Nitriles
  • Pyridazines
  • Pyrroles