Synthesis of Substituted 3(2<i>H</i>)-Furanones Using Alkylative Intramolecular Cyclization of Sulfonium Salts

Inagaki, Sho; Ukaku, Mika; Chiba, Akira; Takahashi, Fumi; Yoshimi, Yasuharu; Morita, Takeshi; Kawano, Tomikazu

doi:10.1021/acs.joc.6b01528

Cited by 11 publications

(12 citation statements)

References 40 publications

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“…[71] Alternatively,a lkylative intramolecular cyclisation of 3-alkoxycarbonyl-2-oxopropyldiphenylsulfonium salts affords 4-alkylated 3(2H)-furanones in good yields (Scheme7b). [72]…”

Section: Synthetic Routes To Furanone Derivativesmentioning

confidence: 99%

The Current Status of O‐Heterocycles: A Synthetic and Medicinal Overview

Singh

Silakari

2018

ChemMedChem

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O-Heterocycles have been explored in the field of medicinal chemistry for a long time, but their significance has not been duly recognised and they are often shunned in favour of N-heterocycles. The design of bioactive molecules for nearly every pathophysiological condition is primarily focused on novel N-heterocycles. The main reasons for such bias include the ease of synthesis and possible mimicking of physiological molecules by N-heterocycles. But considering only this criterion rarely provides breakthrough molecules for a given disease condition, and instead the risks of toxicity or side effects are increased with such molecules. On the other hand, owing to improved synthetic feasibility, O-heterocycles have established themselves as equally potent lead molecules for a wide range of pathophysiological conditions. In the last decade there have been hundreds of reports validating the fact that equally potent molecules can be designed and developed by using O-heterocycles, and these are also expected to have comparably low toxicity. Even so, researchers tend to remain biased toward the use of N-heterocycles over O-heterocycles. Thus, this review provides a critical analysis of the synthesis and medicinal attributes of O-heterocycles, such as pyrones, oxazolones, furanones, oxetanes, oxazolidinones, and dioxolonones, and others, reported in the last five years, underlining the need for and the advantages guiding researchers toward them.

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“…[71] Alternatively,a lkylative intramolecular cyclisation of 3-alkoxycarbonyl-2-oxopropyldiphenylsulfonium salts affords 4-alkylated 3(2H)-furanones in good yields (Scheme7b). [72]…”

Section: Synthetic Routes To Furanone Derivativesmentioning

confidence: 99%

The Current Status of O‐Heterocycles: A Synthetic and Medicinal Overview

Singh

Silakari

2018

ChemMedChem

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“…21b When ethyl 4-chloroacetoacetate ( 34a ) and ethyl 4-bromoacetoacetate ( 34b ) were subjected to the optimal conditions, 35a was observed as a minor product and the dimerization product 36 was the major product (Scheme 8a ). 21a These results indicated that a bulky diphenylsulfonio group was very important for the cyclization as substrates bearing smaller leaving groups (e.g., Cl, Br) underwent intermolecular S N 2 reactions. This strategy also enabled a one-pot preparation of 5-alkoxy-4-alkylfuran-3(2 H )-ones 41 from sulfoniums 37 via alkylation with alkyl halides followed by intramolecular cyclization, showing a wide substrate scope and good functional group tolerance (Schemes 8b and 8c).…”

Section: Electrophilic Alkylation Using Alkylsulfonium Saltsmentioning

confidence: 95%

“…In 2016, Kawano and co-workers disclosed the synthesis of 5-alkoxyfuran-3(2 H )-ones 35 from the intramolecular cyclization of 3-(alkoxycarbonyl)-2-oxopropyl(diphenyl)sulfonium salts 37 in the presence of t -BuOK (Scheme 8a ). 21a Similarly, intramolecular cyclization of (4-aryl-2,4-dioxobutyl)methylphenylsulfonium salts 39 derived from 1-arylethanone 38 produced a family of 5-arylfuran-3(2 H )-ones 40 in excellent yields under ambient conditions (Scheme 8a ). 21b When ethyl 4-chloroacetoacetate ( 34a ) and ethyl 4-bromoacetoacetate ( 34b ) were subjected to the optimal conditions, 35a was observed as a minor product and the dimerization product 36 was the major product (Scheme 8a ).…”

Section: Electrophilic Alkylation Using Alkylsulfonium Saltsmentioning

confidence: 99%

“…This strategy also enabled a one-pot preparation of 5-alkoxy-4-alkylfuran-3(2 H )-ones 41 from sulfoniums 37 via alkylation with alkyl halides followed by intramolecular cyclization, showing a wide substrate scope and good functional group tolerance (Schemes 8b and 8c). 21a In addition, halogenative intramolecular cyclization of 37 with NXS (X = Br, I) conveniently furnished a variety of 4-bromo- or 4-iodo-substituted 5-alkoxyfuran-3(2 H )-ones 42 as useful synthetic building blocks in good to high yields. 21c Acylative intramolecular cyclization of alkylsulfonium salts 44 by in situ formation of a mixed anhydride between carboxylic acid 43 and trifluoroacetic anhydride (TFAA) in the presence of N -methylimidazole, followed by sequential acylation and cyclization, was extensively explored, which provided various 2-substituted 4-oxo-4,5-dihydrofuran-3-carboxylates 45 in good yields (Scheme 8c ).…”

Section: Electrophilic Alkylation Using Alkylsulfonium Saltsmentioning

confidence: 99%

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Alkylation Reactions with Alkylsulfonium Salts

Tian

Zhang

2021

Synthesis

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Application of alkylsulfonium salts as alkyl transfer reagents in organic synthesis has reemerged over the past years. Numerous heteroatom- and carbon-centered nucleophiles, alkenes, arenes, alkynes, organometallic reagents, and others were readily alkylated by alkylsulfonium salts under mild conditions. The reactions feature convenience, high efficiency, readily accessible and structurally diversified alkylation reagents, good functional group tolerance, and a wide range of substrate types, allowing for facile synthesis of various useful organic molecules from the commercially available building blocks. This review summarizes the alkylation reactions using either isolated or in situ formed alkylsulfonium salts via nucleophilic substitution, transition-metal-catalyzed reactions, and photoredox processes.

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“…In 2016, the group of Kawano described an intramolecular cyclization of 3‐alkoxycarbonyl‐2‐oxopropyldiphenyl sulfonium salts towards 5‐substituted‐3(2 H )‐furanones (Scheme 12). [ 16 ] Different sulfonium salts 53 were prepared by treating various substituted 4‐bromo‐acetoacetates with diphenyl sulfide in the presence of AgBF 4 . These sulfonium salts were then allowed to undergo intramolecular cyclization in the presence of a base.…”

Section: Methods For the Synthesis Of 5‐substituted‐3(2h)‐furanonesmentioning

confidence: 99%