93831-13-1Relevant articles and documents
Dioxolanones as Synthetic Intermediates. Part 2. Synthesis of Tetronic Acids and Pulvinones
Ramage, Robert,Griffiths, Gareth J.,Shutt, Fiona E.,Sweeney, John N. A.
, p. 1539 - 1545 (2007/10/02)
The utility of 1,3-dioxolan-4-ones as intermediates in the synthesis of tetronic acids is examined.The reaction of dioxolanone (1) with lithium enolates of 2-substituted methyl or t-butyl acetates at -78 deg C in tetrahydrofuran afforded a general synthesis of 2-substituted tetronic acids (3) - (8).Treatment of (1) with the anions of 2-substituted acetonitriles led to formation of the corresponding 3-substituted-2-aminofuran-4(5H)-ones (13) and (14).A route to unsymmetrically substituted pulvinones by reaction of 5-arylidene-2,2-pentamethylene-1,3-dioxolan-4-ones with appropriately substituted phenylacetic ester anions has been devised.Thus, the preparation of the naturally occurring pigment 3',4',4-trihydroxypulvinone (18) was achieved via intermediate in which the phenolic groups were protected as benzyl ethers.The dioxolanone (26) has been used in the preparation of 2-acyl-4-benzylidenetetronic acids.