Chniti, Sami; Kollar, Laszlo; Benyei, Attila; Takacs, Attila published the artcile< Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation>, Application of C6H8N2, the main research area is quinoline amide preparation chemoselective; iodoquinoline amine carbon monoxide aminocarbonylation palladium catalyst; 6-iodoquinoline; aminocarbonylation; carbon monoxide; double carbonylation; palladium.
The aminocarbonylation of 6-iodoquinoline has been investigated in the presence of large series of amine nucleophiles such as tert-butylamine, cyclohexylamine, furfyrlamine, etc. providing an efficient synthetic route for producing various quinoline-6-carboxamide I (R = cyclohexylaminyl, decan-1-aminyl, 4-methylpiperazin-1-yl, etc.) and quinoline-6-glyoxylamide derivatives II. It was shown, after detailed optimization study, that the formation of amides and ketoamides is strongly influenced by the reaction conditions. Performing the reactions at 40 bar of carbon monoxide pressure in the presence of Pd(OAc)2/2 PPh3, the corresponding 2-ketocarboxamides II were formed as major products (up to 63%). When the monodentate triphenylphosphine was replaced by the bidentate XantPhos, the quinoline-6-carboxamide derivatives I were synthesized almost exclusively under atm. conditions (up to 98%). The isolation and characterization of the new carbonylated products I, II of various structures were also accomplished. Furthermore, the structure of three new mono- and double-carbonylated compounds I, I were unambiguously established by using a single-crystal XRD study.
Molecules published new progress about Amides, oxo Role: SPN (Synthetic Preparation), PREP (Preparation). 3731-53-1 belongs to class pyridine-derivatives, and the molecular formula is C6H8N2, Application of C6H8N2.