22979-24-4Relevant articles and documents
One-Pot Tandem Protocol for the Synthesis of 1,3-Bis(β-aminoacrylate)-Substituted 2-Mercaptoimidazole Scaffolds
Luo, Jian,Chen, Guo-Shu,Chen, Shu-Jie,Li, Zhao-Dong,Zhao, Yu-Lei,Liu, Yun-Lin
, p. 3635 - 3643 (2020)
We have developed a palladium-catalyzed cross-coupling reaction of isocyanides with α-diazoacetates to form active ketenimines and following a 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed aza-Mannich type reaction with various 2-mercaptoimidazoles for the synthesis of 1,3-bis(β-aminoacrylate)-substituted 2-mercaptoimidazole derivatives with structural diversity. In addition, the use of 1H-benzo[d]imidazol-2-ol as the reaction partner also allowed the formation of 1,3-bis(β-aminoacrylate)-substituted 2-benzimidazolinone derivatives with moderate yields (34–52percent). In the aza-Mannich reaction, the regioselective N-attack rather than S-attack or O-attack at the electrophilic central carbon of ketenimines was observed. This tandem sequence is efficient since two C=C and two C?N bonds are consecutively created in one-pot. (Figure presented.).
