Viveki, Amol B.; Pol, Mahesh D.; Halder, Priyanka; Sonavane, Sameer R.; Mhaske, Santosh B. published the artcile< Annulation of Enals with Carbamoylpropiolates via NHC-Catalyzed Enolate Pathway: Access to Functionalized Maleimides/Iso-maleimides and Synthesis of Aspergillus FH-X-213>, Electric Literature of 3893-18-3, the main research area is maleimide preparation; isomaleimide preparation diastereoselective; carbamoylpropiolate unsaturated aldehyde heterocyclization heterocyclic carbene catalyst.
Herein, the N-heterocyclic carbene (NHC)-catalyzed [3+2] annulation of α,β-unsaturated aldehydes RCH=CHC(O)H (R = cyclohexyl, Ph, anthracen-9-yl, pyridin-3-yl, etc.) with carbamoylpropiolates R1NHC(O)CCC(O)OCH2CH3 (R1 = Ph, hexyl, 4-methylcyclohexyl, 4-nitrophenyl, etc.) and di-Et 4,4′-(hexane-1,6-diylbis(azanediyl))bis(4-oxobut-2-ynoate) via an unusual enolate pathway leading to the construction of highly functionalized maleimides I or isomaleimides II and III was reported. 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 I, II and III. 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 IV has also been demonstrated.
Journal of Organic Chemistry published new progress about Alkynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Electric Literature of 3893-18-3.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary