2397-79-7Relevant academic research and scientific papers
Regiodivergent Hydration-Cyclization of Diynones under Gold Catalysis
Mu?oz, Miguel A.,Sanz, Roberto,Solas, Marta,Suárez-Pantiga, Samuel
, p. 7681 - 7687 (2020/10/12)
Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.
Atom-economic synthesis of 4-pyrones from diynones and water
Xu, Yan-Li,Teng, Qing-Hu,Tong, Wei,Wang, Heng-Shan,Pan, Ying-Ming,Ma, Xian-Li
, (2017/01/24)
Transition-metal-free synthesis of 4-pyrones via TfOH-promoted nucleophilic addition/cyclization of diynones and water has been developed. This transformation is simple, atom economical and environmentally benign, providing rapid and efficient access to s
Synthesis of pyran-4-ones from isoxazoles
Li, Chun-Sing,Lacasse, Edith
, p. 3565 - 3568 (2007/10/03)
A synthesis of mono-, di- and tri-substituted pyran-4-ones from isoxazoles is reported. The isoxazoles can be synthesized from readily available starting materials and undergo a reductive cleavage reaction with Mo(CO)6 to generate enamino keton
Synthesis and reactions of reduced flavones
Groundwater, Paul W.,Hibbs, David E.,Hursthouse, Michael B.,Nyerges, Miklos
, p. 163 - 169 (2007/10/03)
The cycloadditions of a series of 4H-pyran-4-ones 3c-e with electron-rich dienes 11a,b to give reduced flavones 12 is described. The subsequent reactions of these reduced flavones with HCl, trifluoroacetic anhydride, ethyl anthranilate 19a and anthranilon
Thermal addition reaction of aroylketene with ethyl vinyl ether: Aromatic substituent effect on aroylketene reactivity
Toda, Jun,Saitoh, Toshiaki,Oyama, Taichi,Horiguchi, Yoshie,Sano, Takehiro
, p. 2457 - 2464 (2007/10/03)
A series of aroylketenes (2) generated by thermolysis of 5-aryl-2,3-dihydrofuran-2,3-diones (1) reacted with ethyl vinyl ether under a thermal condition to give 2,3-dihydro-4H-pyran-4-ones (3) and/or 4H-pyran-4-ones (4). In this reaction the electron withdrawing substituent (NO2, Cl) introduced into the aryl part enhanced the ketene reactivity (2b-e), while the electron donating one (OMe) did not affect its reactivity (2f-g) in a significant extent. The heteroaroylketenes (2h) and (2i) showed a fairly good reactivity.
Synthetic Applications of N-N Linked Heterocycles. Part 12. The Preparation of 4-Alkylthio- and 4-Arylthio-pyridines by Regiospecific Attack of Thioalkoxide Ions on N-(4-Oxopyridin-1-yl)pyridinium Salts
Sammes, Michael P.,Leung, Christopher W. F.,Mak, Chi Keung,Katritzky, Alan R.
, p. 1585 - 1590 (2007/10/02)
Thiolate ions add regiospecifically to N-(4-oxopyridin-1-yl)pyridinium salts (2)-(7) to give in good to excellent yields only the 1,4-dihydropyridine adducts (8)-(13), regardless of whether or not the pyridone moiety carries substituents for sterically shielding the 2- and 6-positions of the pyridinium ring.The addition is believed to be thermodynamically controlled.Decomposition of the dihydro-adducts under free-radical conditions, or by pyrolysis, gives good yields of pyridin-4-yl thioethers (14) and (16) though the reaction failed with the 2-methyl adducts (9).An improved synthesis of 6-methyl-4-oxopyran-2-carboxylic acid is also described.
A CONVENIENT SYNTHESIS OF SUBSTITUTED γ-PYRONES
Koreeda, Masato,Akagi, Hiroshi
, p. 1197 - 1200 (2007/10/02)
An efficient and general synthetic method for various 2-mono- and 2,6-disubstituted γ-pyrones has been developed.This utilizes the C-acylation (70-85percent) of β-methoxy-α,β-enone lithium enolates 4 by acid chlorides 3 followed by the acid-catalyzed cycl
A ONE-STEP SYHTHESIS OF γ-PYRONES
Morgan, Ted A.,Ganem, Bruce
, p. 2773 - 2774 (2007/10/02)
The potassium enolate of 4-methoxy-3-buten-2-one reacts with acid chlorides anhydrides and acylimidazoles by C-acylation and in situ cyclization to afford 2-substituted γ-pyrones directly.
