Rapid Synthesis of 3-Methyleneisoindolin-1-ones via Metal-Free Tandem Reactions of Ester-Functionalized Aziridines
Siyang Xing, Changkun Jin, Panpan Zhang, Jingmeng Yang, Yu‐Xia Liang, Xinglian Ao, Wenyi Pi, Kui Wang, Bolin Zhu
Abstract
We have disclosed a novel metal-free tandem cyclization reaction for the synthesis of 3-methyleneisoindolin-1-ones starting from ester-functionalized aziridines. This strategy can be effectively promoted by DBU and carboxylic acids. Mechanistically, it involves sequential ring opening of aziridines with carboxylic acids, lactamization, and elimination of carboxylic acids.
Topics & Concepts
ChemistryTandemCascade reactionRing (chemistry)Reaction conditionsCombinatorial chemistryCarboxylic acidOrganic chemistryCatalysisMaterials scienceComposite materialSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAdvanced Synthetic Organic Chemistry