104524-22-3Relevant academic research and scientific papers
Ethylidenetetronic Acid and its Derivatives. Condensations with Carbonyl Compounds, leading to Reassignment of Ramigenic Acid from Penicillium charlesii
Begley, Michael J.,Clemo, Nicholas G.,Pattenden, Gerald
, p. 2393 - 2398 (2007/10/02)
Condensation reactions between ethylidenetetronic acid (6) and aryl aldehydes in the presence of weak bases, lead to the 2:1 adducts (8); with 3,4-dimethoxybenzaldehyde the 1:1 adduct (10) is produced concurrently.Reaction between (6) and acetone initially leads to a similar 2:1 adduct i.e. (12), but on further heating in acetone this adduct disproportionates giving the novel dihydopyran (13).The structure of (13) was solved by single crystal X-ray determination.Comparison of spectral data, and synthesis show that the structure of the analogous compound 'ramigenic acid' isolated from Penicillium charlesii should be reassigned as shown in formula (17b).
