Facile synthesis of the spiro-pyridoindolone scaffold<i>via</i>a gold-catalysed intramolecular alkynol cyclisation/hydroindolylation

Shinde, Mahesh H.; Ramana, Chepuri V.

doi:10.1039/d1ob02483c

Cited by 3 publications

(2 citation statements)

References 80 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ramana group reported a catalytic approach for constructing a spiro‐pyridoindolone core, which is found in the indole class of alkaloids (Scheme 20). [37] A gold‐catalyzed 5‐ endo‐dig form of alkynol cyclisation is followed by Friedel– Crafts‐type addition of C2 indole to the resultant dihydrofuran intermediate. The alkynol 42 was reacted under the optimal reaction conditions of 5 mol% AuCl 3 in 1,2‐dichloroethane at room temperature for 15 minutes furnished the desired spirocyclized product 43 in yield of 59–90 %.…”

Section: Intramolecular Gold‐catalyzed Synthesis Of Spirocyclesmentioning

confidence: 99%

See 1 more Smart Citation

Gold‐Catalyzed Synthesis of Spirocycles: Recent Advances

2022

View full text Add to dashboard Cite

Different types of gold‐catalysts with additives yielded high enantioselective and stereoselective spiro carbocyclic and spiro heterocyclic scaffolds. Gold‐catalyzed spirocyclization proceeds through key intermediates like gold‐alkyne and gold‐allene complex which give direct access to spiro products via cyclization, dearomatization, hydroamination, hydroalkoxylation, cascade reaction, etc. This review article aims to provide an overview of gold‐catalyzed reactions for the formation of spirocycles from various substrates, mentioning methodologies, applications, and mechanistic insights.

show abstract

Section: Intramolecular Gold‐catalyzed Synthesis Of Spirocyclesmentioning

confidence: 99%

“…Synthesis of spiro-pyridoindolone core. [37] Scheme 21. Intramolecular dearomatization of phenols and allenoates.…”

Section: Spirocyclization Via Dearomatization Reactionmentioning

confidence: 99%

Gold‐Catalyzed Synthesis of Spirocycles: Recent Advances

2022

View full text Add to dashboard Cite

show abstract

Efficient assembly and anti-tumor evaluation of novel polycyclic [1,2-a]-fused indoles

Guo,

Tian,

et al. 2024

Bioorganic Chemistry

View full text Add to dashboard Cite

Alkoxyalkylation of Electron-Rich Aromatic Compounds

Simon,

Lőrinczi,

Szatmári

2024

IJMS

View full text Add to dashboard Cite

Alkoxyalkylation and hydroxyalkylation methods utilizing oxo-compound derivatives such as aldehydes, acetals or acetylenes and various alcohols or water are widely used tools in preparative organic chemistry to synthesize bioactive compounds, biosensors, supramolecular compounds and petrochemicals. The syntheses of such molecules of broad relevance are facilitated by acid, base or heterogenous catalysis. However, degradation of the N-analogous Mannich bases are reported to yield alkoxyalkyl derivatives via the retro-Mannich reaction. The mutual derivative of all mentioned species are quinone methides, which are reported to form under both alkoxy- and aminoalkylative conditions and via the degradation of the Mannich-products. The aim of this review is to summarize the alkoxyalkylation (most commonly alkoxymethylation) of electron-rich arenes sorted by the methods of alkoxyalkylation (direct or via retro-Mannich reaction) and the substrate arenes, such as phenolic and derived carbocycles, heterocycles and the widely examined indole derivatives.

show abstract

Facile synthesis of the spiro-pyridoindolone scaffoldviaa gold-catalysed intramolecular alkynol cyclisation/hydroindolylation

Abstract: A simple approach for the synthesis of pyridoindolone scaffolds with a spiroannulated tetrahydrofuran ring has been described. The overall process comprises of intramolecular sequential gold-catalysed 5-endo-dig alkynol cycloisomerization and subsequent...

Cited by 3 publications

References 80 publications

Gold‐Catalyzed Synthesis of Spirocycles: Recent Advances

Gold‐Catalyzed Synthesis of Spirocycles: Recent Advances

Efficient assembly and anti-tumor evaluation of novel polycyclic [1,2-a]-fused indoles

Alkoxyalkylation of Electron-Rich Aromatic Compounds

Contact Info

Product

Resources

About