title: Palladium-Catalyzed Oxidative Direct C3- and C7-Alkenylations of Indazoles: Application to the Synthesis of Gamendazole.
abstract: The first palladium-catalyzed oxidative alkenylation of (1H)- and (2H)-indazole derivatives with various olefins is described. The use of Pd(OAc)2 as the catalyst and Ag2CO3 as the oxidant promoted the selective C3-monoalkenylation of (1H)-indazoles and (2H)-indazoles, affording the desired products in good yields. An original oxidative C7-alkenylation of 3-substituted (1H)-indazoles was also developed. The oxidative alkenylation of (1H)-indazole was successfully applied to the total synthesis of the drug candidate gamendazole in a step- and atom-economical fashion.
authors: Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR CNRS, 7311 , BP 6759, Orléans Cedex 2 45067, France.|Faculté des Sciences, Université Mohammed V de Rabat , BP 1014, Avenue Ibn Batouta, 10000 Rabat, Morocco.
authors: Mohammed
authors: M
authors: Naas
authors: Euromed Research Institute, Engineering Division, Euro-Mediterranean University of Fes , Fès-Shore, Route de Sidi Hrazem, 30070 Fès, Morocco.
authors: Saïd
authors: S
authors: El Kazzouli
authors: Faculté des Sciences, Université Mohammed V de Rabat , BP 1014, Avenue Ibn Batouta, 10000 Rabat, Morocco.
authors: El Mokhtar
authors: el M
authors: Essassi
authors: Euromed Research Institute, Engineering Division, Euro-Mediterranean University of Fes , Fès-Shore, Route de Sidi Hrazem, 30070 Fès, Morocco.
authors: Mosto
authors: M
authors: Bousmina
authors: Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR CNRS, 7311 , BP 6759, Orléans Cedex 2 45067, France.
authors: Gérald
authors: G
authors: Guillaumet
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007191:Indazoles; D016877:Oxidants; C530949:gamendazole; D010165:Palladium