39212-21-0Relevant articles and documents
A rapid entry to natural and unnatural disubstituted maleic anhydrides
Adlington, Robert M.,Baldwin, Jack E.,Cox, Rhona J.,Pritchard, Gareth J.
, p. 820 - 822 (2002)
Copper-mediated tandem vicinal difunctionalisation of dimethyl acetylenedicarboxylate, followed in selected cases by oxidation of one of the substituents, provides a versatile and rapid route to a variety of natural and unnatural disubstituted maleic anhydrides.
Annulation of Enals with Carbamoylpropiolates via NHC-Catalyzed Enolate Pathway: Access to Functionalized Maleimides/Iso-maleimides and Synthesis of Aspergillus FH-X-213
Halder, Priyanka,Mhaske, Santosh B.,Pol, Mahesh D.,Sonavane, Sameer R.,Viveki, Amol B.
, p. 9466 - 9477 (2021/07/26)
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.
Regioselective monoalkylation of dimethyl alkylidenesuccinates: Simple approach to dialkyl-substituted maleic anhydrides including chaetomellic acid A
Kshirsagar, Umesh A.,Argade, Narshinha P.
, p. 1804 - 1808 (2011/07/29)
Natural and nonnatural dialkylmaleic anhydrides were readily prepared from dimethyl alkylidenesuccinates by sodium hexamethyldisilazide-induced selective monoalkylation followed by base-catalyzed hydrolysis. Georg Thieme Verlag Stuttgart - New York.
