108237-00-9Relevant articles and documents
Copper-Catalyzed One-Pot Synthesis of 3-(N-Heteroarenyl)acrylonitriles through Radical Conjugated Addition of β-Nitrostyrene to Methylazaarenes
Moreira, Natália M.,Martelli, Lorena S. R.,de Julio, Kiyara I. R.,Zukerman-Schpector, Julio,Opatz, Till,Corrêa, Arlene G.
, p. 4563 - 4570 (2020)
A simple procedure for the copper-catalyzed synthesis of 3-(N-heteroaryl)acrylonitriles was developed. Using a combination of Lewis and Br?nsted acids, this one-pot procedure undergoes via a radical conjugated addition and dehydration processes, without isolation of any intermediate, affording the acrylonitriles. This diastereoselective approach allowed the synthesis of a broad scope of quinazoline derivatives (22 examples) with moderate to good yields and good functional-group tolerance and could be extended to other N-heterocyles such as quinolines and isoquinolines. Based on control experiments, a mechanistic proposal for this new transformation is also presented.
