40941-41-1Relevant academic research and scientific papers
Facile synthesis of 3(2H)-furanones
Panda, Niranjan,Nayak, Dinesh K.
, p. 1093 - 1100 (2018/02/22)
Abstract: A practical method for the synthesis of 3(2H)-furanones including the bullatenone was described. Intramolecular cyclization of 4-hydroxyalkynones in the presence of KOH affords the biologically potent furanones in moderate-to-good yield at room temperature. Synthesis of 4-hydroxyalkynones from the reaction of acid chloride and terminal alkyne in the presence of copper iodide at room temperature was also reported.
Ring Closure to Ynone Systems: 5- and 6-endo- and -exo-dig Modes
Brennan, Colin M.,Johnson, David C.,McDonnell Peter D.
, p. 957 - 962 (2007/10/02)
The rates of cyclisation of 2-hydroxy-2-methyl-5-arylpent-4-yn-3-ones in trifluoroacetic acid are reported.An approximate ρ value of -4.0 (using ?+) and a kinetic isotope effect KTFA/KTFA-d' of 4.2 are observed, which suggest that the reaction proceeds via rate-limiting triple-bond protonation and does not entail carbonyl protonation along the reaction co-ordinate.The base-catalysed ring closure occurs via the vinilyc carbanion.A similar mechanistic picture appears to be involved in the cyclisation of 1-(2-hydroxyphenyl)-3-arylprop-2-yn-1-ones which yield a mixture of flavone and aurone in base, whilst in acid only the flavone is observed.In contrast with recent theoretical studies, the base-catalysed results appear to conform to Baldwin's original proposal of acute-angle approach of a nucleophile to a triple bond.
A Novel and Practical Synthetic Method of 3(2H)-Furanone Derivatives
Sakai, Takashi,Yamawaki, Akitoshi,Ito, Hiroshi,Utaka, Masanori,Takeda, Akira
, p. 1199 - 1201 (2007/10/02)
A novel convenient synthetic method of 5-aryl-2,2-dimethyl-3(2H)-furanones (aryl = C6H5, 2-CH3C6H4, 3-CH3C6H4, 4-CH3C6H4, 2-ClC6H4, 4-ClC6H4, 2,4-Cl2C6H3) is described.It involves the Claisen-Schmidt condensation (potassium hydroxide/ethanol) of aromatic
