Concise and efficient methods for the syntheses of functionalized Indene and Indanone derivatives from Morita-Baylis Hillman (MBH) alcohols via Palladium catalyzed annulations are described. The formation and nature of the product was based on the MBH adduct used and the reaction conditions established after detailed optimization studies. The reaction of Baylis-Hillman alcohols (1 a-m) in presence of Pd(OAc) 2 (5 mol %), P(o-Tol) 3 (20 mol %) , AgOAc (1 eq.) and Na 2 CO 3 (2 eq.) in Dioxane at 120°C under Nitrogen atmosphere provided substituted indenes (2 a-m) in good to excellent yields. While, Indanone derivatives (4 a-f) are obtained from o-halo substituted MBH adducts (3 a-l) when subjected to reaction with Pd (OAc) 2 (3 mol %) and K 3 PO 4 (2.5 eq.) in DMA at 140°C in the absence of any ligand or additive.
The development of a novel heterogeneous polymer supported palladium catalyst for the oxidative C−H olefination of anilides is described. The catalyst was realized by immobilizing Palladium acetate over ethylene diamine modified Polyacrylonitrile (PAN) and characterized by means of FTIR, XRD and XPS analyses which evidenced the complexation of Pd(OAc)2 with the chelating groups in the polymer. The resulting supported complex (en‐PAN‐Pd) was then explored as an efficient and reusable heterogeneous catalyst for ortho selective C−H activation of anilides on reaction with a number of alkyl acrylates. This reaction protocol serves as a useful and greener method for the synthesis of o‐alkenyl anilides under mild reaction conditions. The catalyst also exhibited good recyclability and reusability without losing much catalytic activity.
Quinolines and its derivatives are significant class of heterocyclic compounds which are identified as the key component in many natural products and biologically important molecules. We describe herein a facile method for the synthesis of quinoline derivatives from Morita‐Baylis‐Hillman (MBH) Alcohols
via
Palladium Catalyzed intramolecular aryl amination followed by allylic amination pathway. The reaction between a series of MBH alcohols and amino compounds (Tosyl, aliphatic and aromatic amines) under optimized reaction conditions with Pd(PPh
3
)
2
Cl
2
/DPPP catalyst system, afforded the corresponding 1,2‐dihydroquinolines upto 95 % isolated yield.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.