One-pot tandem synthesis of fluorescent 5-naphthyl-3(2H)-furanones

Малькина, А. Г.; Volostnykh, O. G.; Petrushenko, Konstantin B.; Shemyakina, Olesya A.; Nosyreva, V. V.; Ushakov, Igor А.; Трофимов, Б. А.

doi:10.1016/j.tet.2013.03.007

Cited by 14 publications

(11 citation statements)

References 55 publications

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“…Related tandem reactions involving naphthoic acids, 108 furan and benzofuran carboxylic acids, 109 thiophene and benzothiophene carboxylic acids, 110 and pyrrole and indole carboxylic acids, 111 were also described by Trofimov and co-workers, giving access to a large variety of functionalized 3(2H)-furanones. However, we must note that longer reaction times or the use microwave irradiation (100 °C) were in these cases required to generate the products in good yields.…”

Section: 107mentioning

confidence: 92%

The intermolecular hydro-oxycarbonylation of internal alkynes: current state of the art

González-Liste¹,

Francos²,

García‐Garrido³

et al. 2017

Arkivoc

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The intermolecular addition of carboxylic acids to alkynes is one of the most straightforward and atomeconomical methods currently available for the preparation of synthetically useful enol esters. However, the vast majority of works have focused on the use of terminal alkynes, substrates much more reactive than their corresponding internal counterparts. In fact, efficient and general protocols for hydro-oxycarbonylation of internal alkynes have only seen the light in recent years. In the present review article an overview of the progress made in the field is given. Catalytic reactions promoted by ruthenium, palladium, silver and gold complexes/salts, along with some specific metal-free protocols, are covered.

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Section: 107mentioning

confidence: 92%

The intermolecular hydro-oxycarbonylation of internal alkynes: current state of the art

González-Liste¹,

Francos²,

García‐Garrido³

et al. 2017

Arkivoc

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“…One such recently found approach is the organocatalyzed cascade assembly of functionalized 3(2H)-furanones from available 21 tertiary cyanopropargylic alcohols and carboxylic acids (Scheme 1). This methodology enables the one-pot synthesis of earlier inaccessible diverse 2,3-dihydrofuran structures bearing aromatic (benzoic acid and its derivatives), 22 condensed aromatic (naphthoic acids), 23 and heteroaromatic (furan, 24 thiophene, 25 pyrrole 26 ) substituents.…”

Section: Special Topic Syn Thesismentioning

confidence: 99%

“…Scheme 1 Synthesis of 4-cyano-3(2H)-furanone derivatives from cyanopropargylic alcohols and carboxylic acids Until now, the reaction was considered as chemoselective, [22][23][24][25][26] since only in a few cases trace amounts of side product of unknown structure were discernible. In continuation of a systematic study of this reaction, we have managed to identify these side products as 4-cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans, i.e.…”

Section: Special Topic Syn Thesismentioning

confidence: 99%

“…cyanopropargylic alcohols 1 and carboxylic acids. 21,22,24 According to the latest mechanistic rationalization of this reaction, 23,25 intermediate keto esters of the type 5 are assembled via zwitterions A resulting from nucleophilic attack of the amine catalyst at the triple bond. The exchange of the ammonium function with a carboxylic acid, accompanied by the simultaneous quenching of the carbanionic site, gives carboxylate intermediate B.…”

Section: Special Topic Syn Thesismentioning

confidence: 99%

“…IR and 1 H and 13 C NMR spectra of 3f correspond to literature data. (24), 246 (23), 231 (19), 182 (14), 181 (15), 180 (11), 154 (15), 143 (13), 140 (12), 128 (29), 114 (31), 102 (16), 91 (13), 79 (48), 69 (38), 44 (18), 43 (23), 41 (50), 39 (14).…”

Section: Reaction Of 4-hydroxy-4-methyl-2-pentynenitrile (1a) With 4-mentioning

confidence: 99%

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Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans

et al. 2016

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It is shown for the first time that the reaction of cyanopropargylic alcohols with carboxylic acids in the presence of triethylamine (5-100 mol%) under microwave irradiation (MeCN, 100 °C, 1.2 atm) follows two competing pathways to afford 4-cyano-3(2H)-furanones (1:1 adduct) and 4-cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans (2:1 adduct) in moderate to good yields. The ratio of the products depends on both the reaction conditions (the reactant ratio, catalyst content) and the reactant structure, the 2:1 adduct formation being favored by an excess of cyanopropargylic alcohol, lower catalyst content, and bulky substituents at the carboxylic functions. Both competing reactions proceed via the same intermediates, keto esters, which either intramolecularly cyclize to the 1:1 adducts, or intermolecularly add the second molecule of cyanopropargylic alcohol to give the 2:1 adducts.

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PPh₃⋅HBr‐DMSO Mediated Expedient Synthesis of γ‐Substituted β,γ‐Unsaturated α‐Ketomethylthioesters and α‐Bromo Enals: Application to the Synthesis of 2‐Methylsulfanyl‐3(2 H)‐furanones

Mal

Sharma

Maulik

et al. 2013

Chemistry A European J

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An efficient chemoselective general procedure for the synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters from α,β-unsaturated ketones has been achieved through an unprecedented PPh3 ⋅HBr-DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of α-bromoenals from enals. Furthermore, AuCl3 -catalyzed efficient access to 3(2H)-furanones from the above intermediates under extremely mild conditions are described.

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One-pot tandem synthesis of fluorescent 5-naphthyl-3(2H)-furanones

Cited by 14 publications

References 55 publications

The intermolecular hydro-oxycarbonylation of internal alkynes: current state of the art

The intermolecular hydro-oxycarbonylation of internal alkynes: current state of the art

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans

PPh₃⋅HBr‐DMSO Mediated Expedient Synthesis of γ‐Substituted β,γ‐Unsaturated α‐Ketomethylthioesters and α‐Bromo Enals: Application to the Synthesis of 2‐Methylsulfanyl‐3(2 H)‐furanones

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One-pot tandem synthesis of fluorescent 5-naphthyl-3(2H)-furanones

Cited by 14 publications

References 55 publications

The intermolecular hydro-oxycarbonylation of internal alkynes: current state of the art

The intermolecular hydro-oxycarbonylation of internal alkynes: current state of the art

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydro­furans

PPh3⋅HBr‐DMSO Mediated Expedient Synthesis of γ‐Substituted β,γ‐Unsaturated α‐Ketomethylthioesters and α‐Bromo Enals: Application to the Synthesis of 2‐Methylsulfanyl‐3(2 H)‐furanones

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Product

Resources

About

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans

PPh₃⋅HBr‐DMSO Mediated Expedient Synthesis of γ‐Substituted β,γ‐Unsaturated α‐Ketomethylthioesters and α‐Bromo Enals: Application to the Synthesis of 2‐Methylsulfanyl‐3(2 H)‐furanones