Pd-catalyzed directing-group-assisted regioselective halogenations to C7 of indolines and C8 of tetrahydroquinolines were achieved in good to excellent yields. The practicality and utility of the developed method have been illustrated by various functional group transformations such as arylation, alkenylation, cyanation, and silylation utilizing the installed synthetic handle. The concise synthesis of primaquine, an antimalarial drug, and formal syntheses of two bioactive natural products, hippadine and pratosine, have also been demonstrated.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.0c01963 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of -Aminochalcones with Bromocrotonates.
Org Lett
November 2024
Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, China.
Controlling the selectivity of reactions is a significantly attractive strategy in synthetic organic chemistry. Herein, an efficient base-controlled chemodivergent domino reaction between -aminochalcones and bromocrotonates has been developed. A series of -2,3-disubstituted indolines and cyclopropane-fused tetrahydroquinolines were obtained via two pathways with a broad substrate scope in moderate to excellent yields under transition-metal-free conditions.
View Article and Find Full Text PDFDesign and synthesis of visible light-activatable photocaged peroxides for optical control of ROS-mediated cellular signaling.
Bioorg Med Chem
September 2024
Laboratory of Pharmaceutical and Medicinal Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan. Electronic address:
We designed and synthesized two novel photocaged peroxide compounds, N5TBHP and N6TBHP, featuring nitrogen-containing fused ring coumarin skeletons. Notably, a tetrahydroquinoline fused coumarin derivative, N6TBHP demonstrated significantly higher photocleavage efficiency under visible light at 455 nm compared to N5TBHP, which contains an indoline fused coumarin. This process effectively releases the oxidative stress inducer tert-butylhydroperoxide (TBHP).
View Article and Find Full Text PDFEasy Access to Functionalized Indolines and Tetrahydroquinolines via a Photochemical Cascade Cyclization Reaction.
J Am Chem Soc
May 2024
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Herein, the development of a light-mediated synthesis of functionalized indolines and tetrahydroquinolines is reported. These structural motifs are considered as highly valuable targets, attributed to their widespread occurrence in pharmaceuticals and natural products. The gold-mediated approach offers a direct route to functionalized indolines in yields of up to 81% under mild photochemical conditions.
View Article and Find Full Text PDFCu(I) Complexes Catalyzed the Dehydrogenation of -Heterocycles.
J Org Chem
April 2024
School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, North fourth Road, Shihezi, Xinjiang 832003, China.
A copper-catalyzed method for the dehydrogenation of various nitrogen-containing heterocycles to furnish quinolines and indoles has been developed. A range of 1,2,3,4-tetrahydroquinolines underwent dehydrogenation by employing 2 mol % of copper complex as a catalyst and using O as an oxidant at 120 °C in 1,2-dichlorobenzene to afford the desired quinolines. The method enables the dehydrogenation of a variety of indolines in the presence of 2 mol % of copper complex , using 10 mol % of TEMPO as an additive and O as an oxidant under room temperature in tetrahydrofuran to furnish indoles in high yields.
View Article and Find Full Text PDFVallesamidine and schizozygane alkaloids: rearranged monoterpene indole alkaloids and synthetic endeavours.
Nat Prod Rep
May 2024
Department of Biomedical Engineering and Diagnostic Pharmacy, China Pharmaceutical University, Nanjing, 211198, China.
Covering 1963 to 2023Monoterpene indole alkaloids are the main sub-family of indole alkaloids with fascinating structures, stereochemistry, and diverse bioactivities (, anticancer, anti-malarial and anti-arrhythmic ). Vallesamidine alkaloids and structurally more complex schizozygane alkaloids are small groups of rearranged monoterpene indole alkaloids with a unique 2,2,3-trialkylated indoline scaffold, while schizozygane alkaloids can generate a further rearranged skeleton, isoschizozygane, possessing a tetra-substituted, bridged tetrahydroquinoline core. In this review, the origin and structural features of vallesamidine and schizozygane alkaloids are introduced, and a discussion on the relationship of these alkaloids with aspidosperma alkaloids and a structural rearrangement hypothesis based on published studies is followed.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!