35236-02-3Relevant academic research and scientific papers
Palladium(II)-Catalyzed Substituted Pyridine Synthesis from ?±,?-Unsaturated Oxime Ethers via a C-H Alkenylation/Aza-6?-Electrocyclization Approach
Yamada, Takahiro,Hashimoto, Yoshimitsu,Tanaka, Kosaku,Morita, Nobuyoshi,Tamura, Osamu
supporting information, p. 1659 - 1663 (2021/03/03)
An efficient synthetic method for multisubstituted pyridines from β-aryl-substituted α,β-unsaturated oxime ethers and alkenes via Pd-catalyzed C-H activation has been developed. Systematic optimization of catalyst ligands revealed that sterically hindered
Enantioselective synthesis of β-substituted chiral allylic amines: Via Rh-catalyzed asymmetric hydrogenation
Wang, Qingli,Gao, Wenchao,Lv, Hui,Zhang, Xumu
supporting information, p. 11850 - 11853 (2016/10/07)
An asymmetric mono-hydrogenation of 2-acetamido-1,3-dienes catalyzed by a Rh-DuanPhos complex has been developed. This approach provides easy access to chiral allylic amines with excellent enantioselectivities and high regioselectivities. The products are valuable chiral building blocks for pharmaceuticals.
Quinoline synthesis: Scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes
Austin, Mark,Egan, Oliver J.,Tully, Raymond,Pratt, Albert C.
, p. 3778 - 3786 (2008/10/09)
Irradiation of substituted 2-benzylidenecyclopentanone O-alkyl and O-acetyloximes in methanol provides a convenient synthesis of alkyl, alkoxy, hydroxy, acetoxy, amino, dimethylamino and benzo substituted annulated quinolines. para-Substituents yield 6-substituted-2,3-dihydro-1H-cyclopenta[b] quinolines with 8-substituted products being obtained from ortho-substituted starting materials. Reactions of meta-substituted precursors are highly regioselective, with alkyl substituents leading to 5-substituted 2,3-dihydro-1H-cyclopenta[b]quinolines and more strongly electron-donating substituents generally resulting in 7-substituted products. 2-Furylmethylene and 2-thienylmethylene analogues yield annulated furo- and thieno-[2,3e]pyridines respectively. Sequential E- to Z-benzylidene group isomerisation and six π-electron cyclisation steps result in formation of a short-lived dihydroquinoline intermediate which spontaneously aromatises by elimination of an alcohol or acetic acid. For 2-benzylidenecyclopentanone O-allyloxime, singlet excited states are involved in both steps. The Royal Society of Chemistry 2007.
