An efficient synthesis of sulfonated quinoline diones by copper catalyzed sulfonylation of activated alkenes with sulfonylhydrazides

Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

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“…The Li group employed a mild intramolecular cyclization of ortho‐CN acrylamides for the construction of sulfonated quinoline diones (Eq. 18‐1).…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…Using CuI/(NH 4 ) 2 S 2 O 8 system, the synthesis of 3sulfonylmethyl quinoline-2,4-diones 518 from N-(2cyanoaryl)methacrylamides 516 and sulfonyl hydrazides 517 in MeCNÀ H 2 O at 80°C was performed (Scheme 223). [272] 4-Sulfonylmethylisoquinoline-1,3-diones 521 were obtained in high yields as a result of the reaction between N-alkyl-N-methacryloyl benzamides 519 and aromatic sulfonyl hydrazides 520 in the presence of NaI/TBHP and TBAB without solvent at 90°C (Scheme 224). The reaction proceeds as a cascade of radical transformations including the generation of the sulfonyl radical, its addition to the terminal double bond, and radical cyclization with the aromatic ring.…”

Section: Construction Of Six-membered Heterocyclesmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.

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“…In 2016, Runtao Li and co-workers developed an efficient route for the synthesis of sulfonated quinolines from activated alkenes with sulfonyl-hydrazides via copper-catalyzed sufonylation, the reaction proceeds through radical addition cyclization sequence. [66] (Scheme 11) Initially, the authors utilized N-(2cyanophenyl)-N-methyl acrylamide, 25 and phenyl-sulfonyl hydrazides as the model substrate, then screened the reaction with CuI as a catalyst, (NH 4 ) 2 S 2 O 8 as an oxidant, and acetonitrile/ water (2 : 1) solvent system at 80°C to afford sulfonated quinoline 26 in excellent yields. Further evaluated the reaction scope using a wide variety of N-(2-cyanophenyl) acrylamides and sulfonyl hydrazides, though all the reactions resulted in quantitative product yields.…”

Section: Radical Addition/cyclizationsmentioning

confidence: 99%

Radical Transformations towards the Synthesis of Quinoline: A Review

Teja

Khan

2020

Chemistry An Asian Journal

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Quinoline is considered one of the most ubiquitous heterocycles due to its engaging biological activities and synthetic utility over organic transformations. Over the past few decades, numerous reports have been documented in the synthesis of quinolines. The classical methods including, Skraup, Friedlander, Doebner‐von‐Miller, Conrad‐Limpach, Pfitzinger quinoline synthesis, and so forth, these are the well‐known methods to construct principal quinoline scaffold with several advantages and limitations. Recently, radical insertion or catalyzed reactions have emerged as a powerful and efficient tool to construct heterocycles with high atom efficiency and step economy. In this concern, this minireview mainly focused on the developments of Quinoline synthesis via radical reactions. In addition, a brief description of the preparation procedure, reactivity, and mechanisms is also included, where as possible. Respectively, the synthesis of quinolines is classified and summarized based on its reactivity, so it will help the researchers to grab the information in this exploration area, as Quinolines are promising pharmacophores.

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An efficient synthesis of sulfonated quinoline diones by copper catalyzed sulfonylation of activated alkenes with sulfonylhydrazides

Abstract: A novel and highly efficient cascade synthesis of sulfonated quinoline dione derivatives from N-(2-cyanoaryl) methylacrylamides and sulfonylhydrazides in good yields is described.

Cited by 33 publications

References 33 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

Radical Transformations towards the Synthesis of Quinoline: A Review

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