91909-90-9Relevant academic research and scientific papers
One-Pot Synthesis of α-Ylidene δ-Lactones from Functionalized Allylic Bromides in a Water-Isopropanol Medium
Ferreira, Misael,Bisol, Tula B.,Da Concei??o, Henrique P.,Russo, Theo V. C.,Bortoluzzi, Adailton J.,Sá, Marcus M.
, p. 667 - 676 (2017)
The one-pot microwave-assisted synthesis of a series of α-ylidene δ-lactones from (Z)-2-(bromomethyl)-2-alkenoates (derived from Morita-Baylis-Hillman reaction) in an aqueous environment is reported. The protocol includes regioselective base-mediated allylation of ethyl acetoacetate with (Z)-2-(bromomethyl)-2-alkenoates followed by decarboxylative hydrolysis, carbonyl reduction of the keto carboxylate intermediate, and acid-mediated cyclization of the resulting δ-hydroxy acid to furnish the α-ylidene δ-lactones with good overall yields. The synthesis was also performed in the stepwise mode, which allowed the isolation and full characterization of each intermediate involved in the one-pot method. The main features of this efficient transformation include the fast reaction rates, the use of a benign aqueous medium, the use of inexpensive and readily available reagents, the production of nearly innocuous residues, and the requirement for a single work-up and purification stage at the end of the process.
Synthesis of 3,5,6-trisubstituted α-pyrones from Baylis-Hillman adducts
Kim, Seong Jin,Lee, Hyun Seung,Kim, Jae Nyoung
, p. 1069 - 1072 (2008/02/03)
3,5,6-Trisubstituted α-pyrones were synthesized starting from the Baylis-Hillman adducts. The synthesis was carried out via the sequential introduction of ketone at the primary position of Baylis-Hillman adduct, lactonization, and the following oxidation
