Three-component synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolinones and benzimidazo-[2,1-a]isoquinolin-6(5H)-ones by SO2insertion and radical cascade cyclization

Zhang, Jie; Yang, Zixian; Yu, Jin‐Tao; Pan, Changduo

doi:10.1039/d2ob00409g

Cited by 15 publications

(6 citation statements)

References 74 publications

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“…Based on the observations of control experiments and relevant literature reports, [12,14] a tentative reaction mechanism for the tandem sulfonylation/cyclization of vinyl azides was proposed in Scheme 3. Initially, p ‐toluenediazonium tetrafluoroborates 2 a undergoes decomposition to give the radical intermediate A , which then reacted with K 2 S 2 O 5 via SO 2 insertion to generate the radical B .…”

Section: Resultsmentioning

confidence: 99%

Tandem Sulfonylation/Cyclization of Vinyl Azides with Aryldiazonium Tetrafluoroborates and SO₂

et al. 2022

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An efficient and facile strategy for the synthesis of 6‐(sulfonylmethyl)phenanthridines and its derivatives has been developed via tandem sulfonylation cyclization of vinyl azides under mild conditions in the absence of any catalysts and additives. The reaction simply utilizes easily accessible and cheap K2S2O5 as the sulfur dioxide source, delivering functionalized phenanthridines in moderate to excellent yields with operational simplicity and gram‐scale synthesis, as well as good functional‐group tolerance.

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Section: Resultsmentioning

confidence: 99%

Tandem Sulfonylation/Cyclization of Vinyl Azides with Aryldiazonium Tetrafluoroborates and SO₂

et al. 2022

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“…In 2022, Our group [156] and Wu's group [157] developed the three‐component arylsulfonylation/cyclization of 2‐aryl‐ N ‐methacryloyl indoles with aryldiazonium tetrafluoroborates. Potassium metabisulfite and DABCO ⋅ (SO 2 ) 2 were employed as a SO 2 surrogate, respectively (Scheme 84c).…”

Section: Cyclization Of Alkene‐tethered 2‐arylindoles and 2‐aryl Benz...mentioning

confidence: 99%

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Liu

Wang

2023

Asian J Org Chem

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Ring-fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction of such structures from readily available substrates becomes an important researching topic in organic synthesis. Triggered by the addition of radicals to the (activated or unactivated) double bonds in alkenes, the subsequent intramolecular addition/cyclization leads to polycyclic compounds. Following this procedure, a variety of functionalized ring-fused structures were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, and operational simple approaches toward versatile functionalized polycyclic structures from readily available alkene-based substrates.Here, we summarized the recent achievements on the formation of ring-fused polycyclic structures via the radicaltriggered cascade reactions of alkenes. Construction of polycyclic structures with no less than 3 fused rings developed during the last decade were included in this Review, corresponding mechanisms were also discussed.

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“…The traditional methods were the oxidation of sulfur-containing compounds and the coupling between sulfinate and alkyl/aryl compounds, which were limited in the utilities due to the poor functional group tolerance. In recent years, the direct insertion of sulfur dioxide has been widely used for the facile access to sulfonyl compounds owing to the step economy, which usually treated [DABCO·(SO 2 ) 2 ], inorganic sulfite, and thiourea dioxide as SO 2 surrogates. For example, Wu’s group reported a metal-free synthesis of sulfonylated indolo[2,1- a ]isoquinolines with the use of sulfur dioxide as SO 2 surrogates and aryldiazonium tetrafluoroborates as aryl radical sources in 2022 .…”

Section: Introductionmentioning

confidence: 99%

Visible-Light-Induced Synthesis of Alkylsulfonated Isoquinolinones from 2-Aryl Indoles/Benzimidazoles through Insertion of Sulfur Dioxide

Liu

Guo

et al. 2023

J. Org. Chem.

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A visible-light-induced three-component reaction of 2-aryl indoles/benzimidazoles, Hantzsch esters, and sodium pyrosulfite through a radical cascade cyclization process with the insertion of sulfur dioxide is described. It provides a novel and powerful way for the synthesis of alkylsulfonated isoquinolinones. Hantzsch esters and Na2S2O5 are employed as alkyl radical precursors and SO2 surrogate, respectively. This transformation exhibits good functional group tolerance and substrate applicability under mild conditions.

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Three-component synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolinones and benzimidazo-[2,1-a]isoquinolin-6(5H)-ones by SO₂insertion and radical cascade cyclization

Cited by 15 publications

References 74 publications

Tandem Sulfonylation/Cyclization of Vinyl Azides with Aryldiazonium Tetrafluoroborates and SO₂

Tandem Sulfonylation/Cyclization of Vinyl Azides with Aryldiazonium Tetrafluoroborates and SO₂

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Visible-Light-Induced Synthesis of Alkylsulfonated Isoquinolinones from 2-Aryl Indoles/Benzimidazoles through Insertion of Sulfur Dioxide

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Three-component synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolinones and benzimidazo-[2,1-a]isoquinolin-6(5H)-ones by SO2insertion and radical cascade cyclization

Cited by 15 publications

References 74 publications

Tandem Sulfonylation/Cyclization of Vinyl Azides with Aryldiazonium Tetrafluoroborates and SO2

Tandem Sulfonylation/Cyclization of Vinyl Azides with Aryldiazonium Tetrafluoroborates and SO2

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Visible-Light-Induced Synthesis of Alkylsulfonated Isoquinolinones from 2-Aryl Indoles/Benzimidazoles through Insertion of Sulfur Dioxide

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Three-component synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolinones and benzimidazo-[2,1-a]isoquinolin-6(5H)-ones by SO₂insertion and radical cascade cyclization

Tandem Sulfonylation/Cyclization of Vinyl Azides with Aryldiazonium Tetrafluoroborates and SO₂

Tandem Sulfonylation/Cyclization of Vinyl Azides with Aryldiazonium Tetrafluoroborates and SO₂