Recent developments in the synthesis of furan-2(5H)-ones

Carter, Neil B.; Nadany, Adam E.; Sweeney, Joseph

doi:10.1039/b007664n

Cited by 97 publications

(18 citation statements)

References 59 publications

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“…Besides the biological and pharmaceutical importance, 2(5H)furanone (from here onwards: furanone) and 2(5H)-thiophenone (from here onwards: thiophenone) attract considerable attention as synthetic targets and intermediates [10][11][12][13][14]. Furanone and thiophenone possess an sp 3 carbon atom (at position 5, see Scheme 1) that, in the presence of unequal substituents (at positions 9 and 10), affords chirality.…”

Section: Introductionmentioning

confidence: 99%

Molecular structure and vibrational spectra of 2(5H)-furanone and 2(5H)-thiophenone isolated in low temperature inert matrix

Breda

Reva

Fausto

2008

Journal of Molecular Structure

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The structure and vibrational spectra of two five-membered heterocyclic a-carbonyl compounds have been studied. The experimental FTIR spectra 2(5H)-furanone and 2(5H)-thiophenone monomers isolated in inert argon matrices at 10 K are reported and discussed. The interpretation of the experimental data is supported by vibrational calculations at the MP2 and DFT(B3LYP) levels of theory with the 6-311++G(d,p) basis set. Spectra/structure correlations were extracted from the data calculated for the two title compounds and for their six-membered ring analogues, a-pyrone and thiapyran-2-one. The vibrational frequencies of the C@O, CC, CH and CH 2 moieties were correlated with the ring size, atomic charges and the nature of heteroatom. Natural bond orbital analysis revealed important details of the electronic structure and dominant intramolecular interactions in 2(5H)-furanone and 2(5H)-thiophenone and provided an additional insight into their vibrational spectra.

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Section: Introductionmentioning

confidence: 99%

Molecular structure and vibrational spectra of 2(5H)-furanone and 2(5H)-thiophenone isolated in low temperature inert matrix

Breda

Reva

Fausto

2008

Journal of Molecular Structure

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“…127 °С. 3,4 Dichloro 5 methoxy 2(5H) furanone 19 (2), 3,4 dichloro 5 ethoxy 2(5H) furanone 20 (3), 3,4 dichloro 5 isopropoxy 2(5H) furanone 19 (4), and 3 chloro 5 hydroxy 4 [(4 methylphenyl)thio] 2(5H) furanone 11 (5) were synthesized by known procedures. B.…”

Section: Methodsmentioning

confidence: 99%

“…2(5H) Furanone structural fragments are parts of natural biologically active compounds such as clavacin, penicillic acid, vitamin C, and synthetic pharmaceutical sub stances. [1][2][3][4] The interest in mucochloric acid from the standpoint of theoretical and experimental organic chemistry is due to its structural features (ring-chain tautomerism) and to the presence of a number of reaction centers owing to which this acid and its derivatives can be involved, as effective building blocks, in reactions with nucleophilic, electrophilic, and other reagents. 1 A large number of publications are devoted to reactions of 2(5H) furanones with N , С , О , and Р nucleophiles; however, among reactions with S nucleophiles, only those with thiols were described.…”

mentioning

confidence: 99%

Reactions of 2-mercaptoacetic acid with mucochloric acid and its derivatives

Kurbangalieva¹,

Devyatova²,

Kosolapova³

et al. 2009

Russ Chem Bull

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The stable products of reactions of mucochloric acid and some of its ethers with 2 mer captoacetic acid were synthesized and characterized. The variation of experimental conditions allowed targeted introduction of a sulfur containing fragment into particular position of the heterocycle: the reaction in aqueous potassium hydroxide gives 3 substituted 2(5H) furanone, the triethylamine additive in nonaqueous solvents facilitates the formation of 4 substituted products, and acid catalysis results in the replacement of the hydroxy (methoxy) group at С(5).(3,4 Dichloro 2 oxo 2,5 dihydrofuran 5 ylthio)ethanoic acid and (3 chloro 5 hydroxy 2 oxo 2,5 dihydrofuran 4 ylthio)ethanoic acid were characterized by X ray diffraction; their crystal and gas phase structures were discussed. The 5 monosubstituted product crystallizes as a racemate, while 4 monosubstituted product, as a conglomerate.

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“…Furanones or α,β‐unsaturated lactones are valuable synthons for organic synthesis . Especially, compounds carrying a substituent in the C 5 position have often been used in asymmetric synthesis of biologically active molecules . Among these compounds, derivatives possessing a hydroxyl or an alkoxy substituent in the C 5 position ( I ) represent an important class of synthons (Fig.…”

Section: Introductionmentioning

confidence: 99%

The structure of electronically excited α,β‐unsaturated lactones

Fréneau

Sainte-Claire

Abe

et al. 2016

J of Physical Organic Chem

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A better knowledge of the structure of the electronically excited state of substrates is indispensable for the understanding and optimization of photochemical reactions. For this study, triplet energies of a variety of α,β-unsaturated γ-lactones (furanones) as well as the structures of the vibrationally relaxed triplet state (T 1 ) have been determined using ab initio coupled-cluster (CCSD) method and/or density functional theory (DFT) calculation. A twist of the original planar structure around C = C bond is found in the relaxed triplet state, π-π*. In the 5-membered ring of furanones the contribution of this mode is limited and the pyramidalization in the C 4 position also contributes to the stabilization. The contribution of each stabilization mode is characterized by the dihedral angles and the Mulliken atomic spin densities. The substituent effect on the pyramidalization and the spin density distribution in the C 4 and in the C 5 position are reported. Depending on the substitution in the C 4 position, the orientation of the pyramidalization is either favored syn or anti with respect of the hydroxyl substituent in the C 5 position. Figure 3. Energies of different electronic states for furanone 1. Structures were optimized in the ground state (left-hand side) and in the T 1 state (right-hand side) at the B3LYP/6-31G(d,p) level. Energies for the higher excited states, T 2 , S 1 , and S 2 , were calculated using TD-DFT Chart 1. Model compounds chosen for the computational study. M. FRÉNEAU ET AL. wileyonlinelibrary.com/journal/poc

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Recent developments in the synthesis of furan-2(5H)-ones

Cited by 97 publications

References 59 publications

Molecular structure and vibrational spectra of 2(5H)-furanone and 2(5H)-thiophenone isolated in low temperature inert matrix

Molecular structure and vibrational spectra of 2(5H)-furanone and 2(5H)-thiophenone isolated in low temperature inert matrix

Reactions of 2-mercaptoacetic acid with mucochloric acid and its derivatives

The structure of electronically excited α,β‐unsaturated lactones

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