Direct synthesis of annulated indoles through palladium-catalyzed double alkylations

Gao, Yadong; Li, Jianhua; Bai, Songlin; Tu, Daoquan; Yang, Chao; Z, Ye; Hu, Bingcheng; Qi, Xiangbing; Jiang, Chao

doi:10.1039/d0qo00135j

Cited by 14 publications

(2 citation statements)

References 78 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Probably that spirocyclic compound 212a is formed as a result of the oxidative rearrangement of carbazole and subsequent N-alkylation with norbornene (Scheme 55,b). [241] Oxidation of β-carboline derivatives 211b upon interaction with NBS led to final products 213 in good to excellent yields (70 -94 %) (Scheme 55,c). [242] Spirocyclic compounds can also be obtained from tetrahydro-β-carboline derivatives without the use of oxidation reactions.…”

Section: The Indole Dearomatization Strategy In the Synthesis Of Spirmentioning

confidence: 99%

See 1 more Smart Citation

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

View full text Add to dashboard Cite

The review covers the results of studies published in the literature on the synthesis of spiro-linked heterocycles of the indole, quinoline, benzoxazine, benzothiazine, indenoquinoxaline, pyridopyrimidine, and acridine series. Possible approaches to the synthesis of spirocycles through a sequence of well-known Knoevenagel, Michael reactions, deamination cyclization of 1,2-dicarbonyl, CH-acid compounds, direct cycloaddition of activated olefins to isatins, 3-alkylideneindoles, 2-oxindoles, in situ generated azomethine ylides, indenoquinoxalines are analyzed. Attention is drawn to approaches to the preparation of spiro-fused compounds using reactions of intra-and intermolecular dearomatization of indoles. Recent advances in the synthesis of spiro-linked benzo heterocycles from derivatives of 2-olefin substituted anilines are summarized. The examples of the synthesis of spiro-fused heterocycles by means of metal complexes catalyzed decomposition of diazo compounds are given. Some syntheses of biologically active representatives are shown, as well as the use of transformations of spiroheterocycles in the preparation of other heterocycles.

show abstract

Section: The Indole Dearomatization Strategy In the Synthesis Of Spirmentioning

confidence: 99%

“…The main product of this reaction is tetrahydrocarbazole 211a . Probably that spirocyclic compound 212a is formed as a result of the oxidative rearrangement of carbazole and subsequent N ‐alkylation with norbornene ( Scheme 55 ,b ) [241] …”

Section: Syntheses Of Spiroheterocycles From 3‐alkylidene‐indol‐2‐onementioning

confidence: 99%

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

Ligand‐Promoted Catalyzed Reactions

Bosque,

Gonzalez‐Gomez

2024

Organic Reaction Mechanisms 2020

View full text Add to dashboard Cite

Excited‐State Copper Catalysis for the Synthesis of Heterocycles

et al. 2021

View full text Add to dashboard Cite

Heterocycles are one of the largest groups of organic moieties with significant medicinal, chemical, and industrial applications. Herein, we report the discovery and development of visible‐light‐induced, synergistic excited‐state copper catalysis using a combination of Cu(IPr)I as a catalyst and rac‐BINAP as a ligand, which produces more than 10 distinct classes of heterocycles. The reaction tolerates a broad array of functional groups and complex molecular scaffolds, including derivatives of peptides, natural products, and marketed drugs. Preliminary mechanistic investigation suggests in situ generations of [Cu(BINAP)2]+ and [Cu(IPr)2]+ catalysts that work cooperatively under visible‐light irradiation to facilitate catalytic carbo‐aroylation of unactivated alkenes, affording a wide range of useful heterocycles.

show abstract

Direct synthesis of annulated indoles through palladium-catalyzed double alkylations

Abstract: A facile, one-step synthesis of annulated indoles from (N–H) indoles and dibromoalkanes was developed through a palladium-catalyzed double alkylation process.

Cited by 14 publications

References 78 publications

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Ligand‐Promoted Catalyzed Reactions

Excited‐State Copper Catalysis for the Synthesis of Heterocycles

Contact Info

Product

Resources

About