Selective monoacetalization of lawsone inverts the site-selectivity of the Diels–Alder reactions of its alkylidene derivatives favoring the protected β-lapachone derivatives.

Piano-stool Ru(ii) complexes incorporating 2-hydroxymethylidene-indene-1,3-dione ligands exhibit promising anticancer activity against four human ovarian cancer cell lines.

Thermal decomposition of the phenyliodonium ylide of lawsone gives rise to a highly reactive cyclic α,α'-dioxoketene, indanedioneketene, which reacts with electron-rich dienophiles such as enol ethers to afford [4 + 2] cycloadducts. The initially formed 2,3-dihydro-2-alkoxy-indeno[1,2-b]pyrano-4,5-diones are labile compounds since through an opening of the pyranone ring upon heating they easily tautomerize to alkoxyallylidene-indenedione derivatives and under acid-catalysis they are additionally transformed to 2-(1,3-dihydroxyallylidene)-1H-indene-1,3(2H)-dione or by loss of alcohol to indeno[1,2-b]pyran-4,5-diones. A DFT study explains the polar nature of the cycloaddition reaction, the observed reactivity and suggests a possible mechanism operating in these reactions.