Fe-Catalyzed Pictet-Spengler-Type Cyclization via Selective Four-Electron Reductive Functionalization of CO2
Herein, we describe a novel catalytic Pictet-Spengler-type cyclization using CO2 as a nontoxic and sustainable C1 feedstock with environmentally benign and non-precious-metal iron as catalyst. The reaction is achieved by selective four-electron reduction of CO2 into methylene level intermediate through carefully tuning the reaction parameters. A variety of tetrahydro-β-carbolines and other nitrogen-containing heterocycles can be easily obtained under mild conditions. Mechanistic studies have shown that tetrahydro-β-carbolines are probably obtained via spiroindolenine intermediates.
Li, Wen-Duo,Chen, Jie,Zhu, Dao-Yong,Xia, Ji-Bao
supporting information
p. 614 - 620
(2021/02/12)
Spiro[pyrrolidine-3, 3′-oxindoles] and their indoline analogues as new 5-HT6 receptor chemotypes
Synthetic derivatives of spiro[pyrrolidinyl-3, 3′-oxindole] alkaloids (coerulescine analogues) were investigated as new ligands for aminergic G-protein coupled receptors (GPCRs). The chemical starting point 2′-phenylspiro[indoline-3, 3′-pyrrolidin]-2-one scaffold was identified by virtual fragment screening utilizing ligand- and structure based methods. As a part of the hit-to-lead optimization a structure-activity relationship analysis was performed to explore the differently substituted 2′-phenyl-derivatives, introducing the phenylsulphonyl pharmacophore and examining the corresponding reduced spiro[pyrrolidine-3, 3′-indoline] scaffold. The optimization process led to ligands with submicromolar affinities towards the 5-HT6 receptor that might serve as viable leads for further optimization.
Kelemen, ádám A.,Satala, Grzegorz,Bojarski, Andrzej J.,Keseru, Gy?rgy M.
(2018/01/17)
RhII2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides
Approaching all isomers: A range of α-, β- and δ-carbolinium ions are readily available from ortho-substituted aryl azides using a rhodium(II) carboxylate catalyst (see scheme). The carbolinium ions are readily reduced to afford tryptolines or deprotonated to access pyridoindoles. This [RhII2]-catalyzed C-H bond amination was used in the synthesis of (±)-horsfiline and neocryptolepine. esp=α,α,α',α'- tetramethyl-1,3-benzenedipropionate. Copyright
Pumphrey, Ashley L.,Dong, Huijun,Driver, Tom G.
p. 5920 - 5923
(2012/08/07)
Lactamisation of 4.9-dihydropyrano[3.4-b]indol-1(3H)-ones. A new synthetic route to the β-carboline ring system
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Lehmann,Ghoneim,El-Gendy
p. 30 - 36
(2007/10/02)
Preparation of vincadifformine and related derivatives
This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of among other alkaloids vincamine and other similar compounds possessing interesting psychopharmacologic properti
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(2008/06/13)
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