53164-69-5Relevant academic research and scientific papers
Cyclocondensation of α-aminonitriles and enones: A short access to 3,4-dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-trisubstituted pyrroles
Bergner, Ines,Wiebe, Christine,Meyer, Nino,Opatz, Till
, p. 8243 - 8253 (2009)
(Chemical Equation Presented) The reaction of α,β-unsaturated carbonyl compounds with aminoacetonitrile hydrochloride furnishes 3,5-disubstituted 3,4-dihydro-2H-pyrrole-2-carbonitriles in a one-pot reaction sequence. While these products can serve as starting materials for the preparation of polysubstituted pyrrolizidines, they are kinetically stable against the base-induced elimination of HCN. In contrast, their 2-substituted analogues obtained from α-substituted α-aminonitriles can be readily converted to the corresponding 2,3,5-trisubstituted pyrroles under microwave irradiation. The key step presumably involves the thermal electrocyclization of a stabilized 2-azapentadienyl anion formed by condensation of the reactants and subsequent deprotonation.
