The controlled mono-addition of indolizines to isatins under very mild conditions is described. The reaction occurs in water using diphenylphosphate as catalyst, which is dramatically accelerated by surfactant addition. 3-hydroxy-3-indolizinyl-2-oxindoles...
Indolizines fused with a seven-membered ring were identified as promising anticancer scaffolds and had their cytotoxicity increased up to twenty times by late-stage functionalization.
<p>The controlled mono-addition of indolizines to isatins under very mild conditions is described. The reaction occurs in water using diphenylphosphate (DPP) as catalyst and is dramatically accelerated by adding a surfactant (sodium dodecyl sulfate – SDS). Using this methodology, 19 new 3-hydroxy-3-indolizinyl-2-oxindoles scaffolds were synthesized (up to >99% yield). Notably, in organic solvents only bis-addition products were observed, in poor yields and in prolonged times. The very low solubility of the mono-addition product in water was determinant for the observed selectivity .<br></p>
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.