Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating

Li, Wei-Le; Liu, Bao-Yang; Li, Chun-Mei; Wang, Xiang; Hao, Wen-Juan; Jiang, Bo

doi:10.1016/j.tetlet.2024.154962

Tetrahedron Letters

2024

DOI: 10.1016/j.tetlet.2024.154962

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Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating

Wei-Le Li,

Bao-Yang Liu,

Chun-Mei Li

et al.

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2024

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Cited by 3 publications

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A Catalytic Intramolecular Aldehyde–Alkyne Metathesis Approach to Azepino[1,2‐a]indoles

Deka,

Das,

Nath

et al. 2024

Adv Synth Catal

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Reported herein is a method for the construction of azepino[1,2‐a]indoles via an intramolecular aldehyde–alkyne metathesis of 1‐(5‐aryl‐4‐pentynyl)indole‐2‐carbaldehydes. This Sc(OTf)3‐catalyzed reaction has several remarkable features, such as ready accessibility of the starting materials, broad substrate scope, operational simplicity, and high yields. The practicality of the process and the synthetic potential of the products were demonstrated with an upscaling experiment and downstream synthetic derivatizations of the obtained products. We have also extended this methodology to synthesize a 6,7‐dihydropyrido[1,2‐a]indole derivative.

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A Catalytic Intramolecular Aldehyde–Alkyne Metathesis Approach to Azepino[1,2‐a]indoles

Deka,

Das,

Nath

et al. 2024

Adv Synth Catal

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Yb(OTf)₃‐Catalyzed C=C Bond Cleavage‐Reassembly Enabling Bicyclization: Regioselective Synthesis of Heteroarylated Pentacyclic Indoles

Liu,

Zhu,

Liu

et al. 2024

Adv Synth Catal

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An Yb(OTf)3‐catalyzed [2+2] cycloaddition /retro‐electrocyclization (CA‐RE)/bicyclization of 1‐(2‐aminoarylaklynyl)‐naphthalen‐2‐ols and 3‐alkylideneoxindoles is reported, enabling a direct C=C bond cleavage‐reassembly process to regioselectively synthesize a variety of quinoline‐tethered benzo[5,6]chromeno[2,3‐b]indoles in 31–84% yields. Exchanging the amino group for a hydroxyl group in the arylalkynyl unit of the naphthalen‐2‐ol substrate resulted in chromenyl chromeno[2,3‐b]indoles via a similar cascade process.

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DBU‐Catalyzed Vinylogous Reaction of 3‐Cyano‐4‐methylcoumarins with 3‐Arylsulfonyl‐3‐indolyloxindoles

Mritunjay,

Sharma,

Singh

et al. 2024

ChemistrySelect

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An efficient metal‐free DBU catalyzed approach for the construction of biologically significant quaternary carbon centered C‐3 functionalized 2‐oxindole derivatives through vinylogous reaction of 3‐cyano‐4‐methylcoumarins with 3‐arylsulfonyl‐3‐indolyloxindoles has been developed for first time. The developed protocol is simple, cost‐effective, and producing the desired products in good yields, without utilizing potentially harmful chemicals. Moreover, the synthesized 3,3‐disubstituted 2‐oxindole molecules contain established pharmacophors in their structure, i. e., oxindole‐, indole‐ and coumarin‐ moieties, which makes them a valuable candidate for drug development process.

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Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating

Cited by 3 publications

References 54 publications

A Catalytic Intramolecular Aldehyde–Alkyne Metathesis Approach to Azepino[1,2‐a]indoles

A Catalytic Intramolecular Aldehyde–Alkyne Metathesis Approach to Azepino[1,2‐a]indoles

Yb(OTf)₃‐Catalyzed C=C Bond Cleavage‐Reassembly Enabling Bicyclization: Regioselective Synthesis of Heteroarylated Pentacyclic Indoles

DBU‐Catalyzed Vinylogous Reaction of 3‐Cyano‐4‐methylcoumarins with 3‐Arylsulfonyl‐3‐indolyloxindoles

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Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating

Cited by 3 publications

References 54 publications

A Catalytic Intramolecular Aldehyde–Alkyne Metathesis Approach to Azepino[1,2‐a]indoles

A Catalytic Intramolecular Aldehyde–Alkyne Metathesis Approach to Azepino[1,2‐a]indoles

Yb(OTf)3‐Catalyzed C=C Bond Cleavage‐Reassembly Enabling Bicyclization: Regioselective Synthesis of Heteroarylated Pentacyclic Indoles

DBU‐Catalyzed Vinylogous Reaction of 3‐Cyano‐4‐methylcoumarins with 3‐Arylsulfonyl‐3‐indolyloxindoles

Contact Info

Product

Resources

About

Yb(OTf)₃‐Catalyzed C=C Bond Cleavage‐Reassembly Enabling Bicyclization: Regioselective Synthesis of Heteroarylated Pentacyclic Indoles