69556-70-3Relevant academic research and scientific papers
Pseudoesters and derivatives xxxvi. reactions of enolates of 5-ethylthiofuran-2(5h)-ones with aromatic aldehydes: A synthesis of losigamone
Rosario Martin,Victoria Martin,De Guere?u, Ana Martinez,Luis Ortego
, p. 191 - 198 (1996)
The furanones (3a) and (3b), key intermediates in our approach to losigamone (12), have been prepared by reaction of 2-chlorobenzaldehyde with the enolates (2A) and (2B) of the corresponding tetronic acid derivatives (2a) and (2b). The reductiv
Lewis Acid Mediated Addition of Indoles and Alcohols to Tetronic Acid and Tetramic Acids
Banales Mejia, Fernando,Lafferty, Megan M.,Melvin, Sophia J.,Truax, Nathanyal J.,Kean, Maeve H.,Pelkey, Erin T.
, p. 260 - 264 (2017)
The electrophilic substitution of indoles with tetronic acid and N-acetyltetramic acid mediated by BF3·OEt2 was investigated. This strategy allowed for the preparation of nine indole-substituted furan-2-ones (indolyl-γ-lactones) and 3-pyrrolin-2-ones (indolyl-γ-lactams) and is more straightforward than previously reported synthetic methods. During the course of our investigation, we also discovered a facile synthesis of tetronates and a tetramate via a BF3-mediated addition of alcohols to tetronic acid and N-acetyltetramic acid, respectively.
Highly efficient 4-O-alkylations of tetronic acids involving oxyphosphonium intermediates
Paintner, Franz F.,Allmendinger, Lars,Bauschke, Gerd
, p. 83 - 86 (2007/10/03)
4-Alkoxy-5H-furan-2-ones were prepared in fair to high yields by regioselective 4-O-alkylation of tetronic acids with stoichiometric amounts of primary and secondary alcohols. This approach involves the intermediacy of (5-oxo-2,5-dihydrofuran-3-yloxy) phosphonium trifluoromethanesulfonates, which were generated in situ on reaction of tetronic acids with triphenylphosphonium anhydride trifluoromethanesulfonate (Hendrickson's reagent).
Methyl (E)-4-chloro-3-methoxy-2-butenoate: An extremely versatile four carbon building block
Duc,McGarrity,Meul,Warm
, p. 391 - 394 (2007/10/02)
Methyl (E)-4-chloro-3-methoxy-2-butenoate (3a) is inexpensively prepared from methyl 4-chloroacetoacetate using thionyl chloride and methanol on an industrial scale. Many nucleophilic substitution reactions of chloride, which are impossible with the unpro
Synthetic Routs to the Piperolides, Faydenolides, Epoxypiperolides, and Related Compounds
Pelter, Andrew,Al-Bayati, Redha I. H.,Ayoub, Miqdad T.,Lewis, Wynn,Pardasani, Pushpa,Hansel, Rudolf
, p. 717 - 742 (2007/10/02)
Syntheses of the piperolides, the faydenolides, epoxypiperolide, and related compounds are described. (+/-)-Narthogenin is also efficiently produced.
Regioselectivity control in metal hydride reductions of substituted maleic anhydrides
Kayser, Margaret M.,Breau, Livain,Eliev, Sonia,Morand, Peter,Ip, H. S.
, p. 104 - 109 (2007/10/02)
A systematic study of reductions of unsymmetrically substituted maleic anhydrides by a variety of metal hydride reagents indicates that the high regioselectivity observed in these reactions is controlled chiefly by electronic factors.
Reaction of Methyl Tetronate with some Amines. Synthesis of Substituted 4-Aminobut-2-enolides
Shandala, Mowafak Y.,Ayoub, Mikdad T.,Mohammad, Moyayed J.
, p. 1753 - 1754 (2007/10/02)
A series of substituted 4-aminobut-2-enolide derivatives have been synthesized by reaction of a variety of substituted amines with methyl tetronate.The (1)H and (13)C nmr spectral analysis of all compounds synthesized are given.
