146725-29-3Relevant articles and documents
Solvent-free condensation of arylacetonitrile with aldehydes
Guillot, Régis,Loupy, André,Meddour, Abdelkrim,Pellet, Michèle,Petit, Alain
, p. 10129 - 10137 (2005)
The condensation of a series of arylacetonitriles with aldehydes can be carried out by mixing equivalent amounts of reagents with neat powdered KOH at room temperature for 3-60 min depending on the aldehyde steric hindrance. At higher temperature (110°C), yields were generally higher and purity increased within very short reaction times (1-5 min). With pentamethylphenylacetonitrile, a phase transfer agent was necessary to give a satisfactory yield.
Regioselective preparation of 2-substituted 3,4-diaryl pyrroles: A concise total synthesis of ningalin B
Bullington, James L.,Wolff, Russell R.,Jackson, Paul F.
, p. 9439 - 9442 (2007/10/03)
Methylisocyanoacetate undergoes a 2 + 3 cycloaddition with α,β-unsaturated nitriles to provide a regioselective synthesis of 2-substituted 3,4-diaryl pyrroles. The ease of preparation of α,β-unsaturated nitriles allows the rapid synthesis of pyrroles with varied substituents. Using this method, a key intermediate (1) for the synthesis of the marine natural products lukianol A, lamellarin O, and lamellarin Q was prepared in two steps. A total synthesis of ningalin B (11) was also accomplished utilizing this methodology.
