Intramolecular Formal [4 + 2] Cycloadditions: Synthesis of Spiro Isoindolinone Derivatives and Related Molecules
Yarkali Krishna, Fujie Tanaka
Abstract
Acid-catalyzed intramolecular reactions of isoindolinone-derived hydroxylactam derivatives bearing enones or enals that afford spiro isoindolinone derivatives and related molecules have been developed. From the hydroxylactam moieties, N-acylenamides were generated in situ and reacted with the enone and the enal moieties via formal [4 + 2] cycloaddition reactions to construct cyclohexanone- and dihydropyran-fused ring systems and the spiro ring systems.
Topics & Concepts
ChemistryCyclohexanoneIntramolecular forceRing (chemistry)CycloadditionDihydropyranMoleculeEnoneCombinatorial chemistryStereochemistryCatalysisOrganic chemistrySynthesis and pharmacology of benzodiazepine derivativesSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions