Synthesis of Ester-Substituted Polycyclic N-Heteroaromatics via Photocatalyzed Alkoxycarbonylation/Tricyclization Reactions of Enediyne in Continuous Flow Conditions

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 20, 2025

For the first time, a photoredox-catalyzed alkoxycarbonylation/tricyclization reaction was developed by employing readily accessible enediynes and alkyloxalyl chlorides as starting materials, enabling synthesis of ester-substituted polycyclic N-heteroaromatics under mild conditions through radical-mediated mechanism. This photocatalytic strategy is notable for its exceptional compatibility with diverse functional groups, scalability, efficiency in formation rings chemical bonds. Notably, continuous flow photocatalysis technology markedly improved these reactions compared to equivalent batch reactions, efficiently decreasing times merely 40 min.

Язык: Английский

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Synthesis of Alkylsulfonyl‐Substituted Indolo[2,1‐a]Isoquinolines via Photoredox‐Catalyzed Radical‐Cascade Addition/Sulfonylation/Cyclization with DABCO ⋅ (SO₂)₂ and Thianthrenium Salts

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(4), С. 555 - 567

Опубликована: Янв. 18, 2023

Abstract A direct, visible‐light‐mediated, radical‐cascade addition/sulfonylation/cyclization reaction with DABCO ⋅ (SO 2 ) and thianthrenium salts is reported herein. This protocol provides operationally‐convenient access to various sulfonated functionalized indole [2,1‐a] isoquinolines under mild conditions. transformation features high functional‐group tolerance, operational ease, broad substrate scope. Preliminary studies reveal that the method undergoes a radical pathway. magnified image

Язык: Английский

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Synthesis of ester-containing phenanthridinesviaphotoredox-catalyzed radical cascade cyclization ofN-arylacrylamides with alkyloxalyl chlorides

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(16), С. 3995 - 4001

Опубликована: Янв. 1, 2023

An alkoxycarbonyl-radical-triggered cascade cyclization reaction of N -( o -cyanobiaryl)acrylamides with alkyloxalyl chlorides is developed, leading to diverse ester-containing phenanthridines.

Язык: Английский

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Regioselective intramolecular cyclization of o-alkynyl arylamines with the in situ formation of ArXCl to construct poly-functionalized 3-selenylindoles

RSC Advances, Год журнала: 2023, Номер 13(9), С. 6210 - 6216

Опубликована: Янв. 1, 2023

In this article, a practical and metal-free method for the synthesis of poly-functionalized 3-selenyl/sulfenyl/telluriumindoles from

Язык: Английский

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Visible‐light‐mediated synthesis of 3‐arylsulfonylated thioflavones using an in situ activation strategy

Bulletin of the Korean Chemical Society, Год журнала: 2023, Номер 44(11), С. 921 - 925

Опубликована: Авг. 30, 2023

Abstract We have developed a visible‐light‐mediated synthesis of 3‐arylsulfonylated thioflavones using an in situ‐activation strategy. The reaction proceeds through one‐pot, three‐component pathway, without the need for sensitive or harsh conditions. Organic photocatalysts were employed to generate aryl radicals more efficiently from diazonium salts generated situ. This method enables amines and methylthiolated alkynones, utilizing potassium metabisulfite as inexpensive source sulfur dioxide. resulting products obtained under mild approach provides efficient alternative pathway synthesizing thioflavone derivatives, which are prevalent among various bioactive compounds.

Язык: Английский

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Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones

Green Synthesis and Catalysis, Год журнала: 2023, Номер unknown

Опубликована: Окт. 1, 2023

A metal-free visible-light-induced synthesis of aza-polycyclic aromatic hydrocarbons via cascade alkylation/cyclization N-methacryloyl-2-phenylbenzimidazole was developed. The reaction carried out with inactive alkanes and cyclic ethers as alkylation reagents, phenanthrenequinone (PQ) a direct hydrogen-atom transfer (HAT) photocatalyst. desired products were obtained in moderate to good yields at room temperature under air.

Язык: Английский

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Three‐Component Synthesis of 3‐(Arylsulfonyl)benzothiophenes Using Acetic Acid as a Quencher for Methyl Radical‐Mediated Side Reactions

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(9), С. 1514 - 1520

Опубликована: Март 16, 2023

Abstract A one‐pot, three‐component synthesis of 3‐(arylsulfonyl)benzothiophenes was developed. The reaction did not require any catalysts or additives. desired products were obtained via an intramolecular radical cyclization. Acetic acid employed as the solvent and a quencher for side reactions involving methyl radicals. Moreover, inexpensive potassium metabisulfite used sulfur dioxide surrogate. This process provides more opportunities synthesizing benzothiophene derivatives, which are found in many bioactive compounds. magnified image

Язык: Английский

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Catalyst‐Free, One‐Pot, Three‐Component Synthesis of 3‐Arylsulfonylated Thioflavones

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(17), С. 3088 - 3093

Опубликована: Авг. 3, 2022

Abstract A one‐pot, three‐component synthesis of 3‐arylsulfonylated thioflavones has been developed. The reactions were carried out without using any catalysts or additives. desired products obtained through intramolecular radical cyclization. This process provides an alternative route for the thioflavone derivatives, which have found in various bioactive compounds. magnified image

Язык: Английский

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Organophotocatalytic cascade cyclization reactions for the synthesis of cyanoalkyl indole[2,1-a]isoquinolinones

New Journal of Chemistry, Год журнала: 2023, Номер 47(39), С. 18354 - 18358

Опубликована: Янв. 1, 2023

Organophotocatalytic cascade cyclization of oxime esters with 2-aryl- N -methacryloyl indoles for the construction cyanoalkyl indolo[2,1- a ]isoquinolinones was developed.

Язык: Английский

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Synthesis of Amide-Containing Indolo[2,1-a]isoquinoline Derivatives via Palladium-Catalyzed Cascade Reactions

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 8, 2024

A convenient palladium-catalyzed cascade cyclization reaction for the construction of amide-containing indolo[2,1-

Язык: Английский

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