33176-11-3Relevant academic research and scientific papers
Synthesis and structural characterization of a fused bispyrone and preparation of the first metal bispyrylium complexes
Waynant, Kristopher V.,White, James D.,Zakharov, Lev
, p. 5304 - 5306 (2010)
Dehydroacetic acid reacts with acetic anhydride in the presence of perchloric acid to give a salt which upon careful neutralization affords a fused bis-γ-pyrone. The bis-γ-pyrone forms stable metal complexes with Li, Mg, Cu(ii), Ni(ii), Zn, Fe(ii), Co(ii) and Ba perchlorates whose crystal structures reveal that the ligand possesses significant bispyrylium character while the metal is coordinated at the negatively charged edge of the structure.
Lewis acid mediated condensation reactions of α,β-unsaturated acids with 4-hydroxy-2-pyrones. A concise structural assignment of Fleischmann's α,α-bispyrone and Praill's α,γ-bispyrone
Zehnder, Luke R.,Dahl, Jason W.,Hsung, Richard P.
, p. 1901 - 1905 (2007/10/03)
Unambiguous assignments of Fleischmann's α,α-bispyrone 3 and Praill's α,γ-bispyrone 6 have been carried out by exploring Lewis acid mediated condensation reactions of α,β-unsaturated carboxylic acids with 4-hydroxy- 2-pyrones. This protocol is shown to be useful for synthesis of a BCDE-ring tetracyclic analog of arisugacin. (C) 2000 Elsevier Science Ltd.
Reactions of fused and unfused α-pyrones with magnesium alkoxide, sodium alkoxide and water as the nucleophile: effects of chelation
Crombie, Leslie,Games, David E.,James, Alun W. G.
, p. 2715 - 2724 (2007/10/03)
The reactions between a series of α-pyrones (two mono- and three fused) and the non-chelating base sodium alkoxide, the chelating base magnesium alkoxide and water as the nucleophile, have been studied.Aromatic and other products formed reflect the points of attack on the pyrone systems and when sodium methoxide is used the ensuing cyclisation is preferentially by aldol mechanisms.The employment of excess magnesium methoxide or ethoxide gives magnesium-chelated precursors and the nature of products now depends on these intermediates, and the protection afforded by such magnesium chelation to the reaction products.In the case of structures containing chelated β-keto ester features the chelates are screened from attack as aldol acceptors, but are effective Claisen acceptors.In such chelates an adjacent methylene is activated by further magnesium alkoxide to act as an aldol or Claisen donor.These contrasting aldol/Claisen reactivities, as between a non-chelating and a chelating base, are illustrated in the ensuing chemistry of the pyrones.Treatment with water releases the main carbon chain with decarboxylation, from which new products may form.
2,7-Dimethyl-4H-pyrano-2H-pyran-4,5-dione, a Novel Product in the Base-catalysed Self-condensation of Ethyl Acetoacetate : Carbon-13 NMR Spectral Studies
Talapatra, Sunil K.,Basak, Amit,Maiti, Bhim C.,Talapatra, Bani
, p. 546 - 548 (2007/10/02)
Self-condensation of ethyl acetoacetate (EAA) in the presence of a small amount of sodium bicarbonate affords, in addition to the earlier reported dehydroacetic acid (II) (45 percent), a new fused γ-pyrono-pyrone derivative in 40 percent yield, the structure of which has been shown to be 2,7-dimethyl-4H-pyrano-2H-pyran-4,5-dione (III) mainly based on PMR and 13C NMR spectral results and supported by UV, IR and mass spectral data.Compound (II) upon refluxing with EAA in water containing pyridine gives III while EAA under similar condition neither affords II nor III and remains mostly unchanged, supporting the postulated mechanism of formation of III via II. 13C NMR spectral data of II have also been discussed.
