1049696-89-0Relevant academic research and scientific papers
Annulation of Enals with Carbamoylpropiolates via NHC-Catalyzed Enolate Pathway: Access to Functionalized Maleimides/Iso-maleimides and Synthesis of Aspergillus FH-X-213
Viveki, Amol B.,Pol, Mahesh D.,Halder, Priyanka,Sonavane, Sameer R.,Mhaske, Santosh B.
, p. 9466 - 9477 (2021)
Herein we report the N-heterocyclic carbene (NHC)-catalyzed [3 + 2] annulation of α,β-unsaturated aldehydes with carbamoylpropiolates via an unusual enolate pathway leading to the construction of highly functionalized maleimides or isomaleimides. The electronic effect imposed by the alkyl/aryl group present on the amide nitrogen of carbamoylpropiolates plays a crucial role in the selective formation of these important five-membered heterocyclic building blocks. The developed protocol is mild and tolerates a wide range of substituents on both substrates. The application of this protocol in the synthesis of the antibacterial natural product Aspergillus FH-X-213 has also been demonstrated.
General strategy for the synthesis of natural and unnatural dialkylmaleic anhydrides
Haval, Kishan P.,Argade, Narshinha P.
, p. 6936 - 6938 (2008/12/22)
(Chemical Equation Presented) Starting from alkylidenesuccinimides, a wide range of dialkylmaleic anhydrides have been synthesized via the generation of a carbanion on a succinimide unit and its condensation with various alkyl halides as the key reaction.
