Spirocyclohexylindolinone is used as a moiety in drug substances. A number of synthetic methods have been suggested to introduce the cyclohexyl ring into the C(3) position of N-protected indolinones, which complicates their preparation. A previously developed, consecutive, one-pot, multi-component method is studied from a mechanistic aspect. We set out to clarify the details of this mechanism and the role of the acryl ester as a reagent and a protecting group in the same flask, by using theoretical and analytical methods, in order to optimise the preparative conditions. A mechanistic energy profile of the reaction is computed at the DFT level of theory.
- Density functional calculations
- Michael addition
- Reaction mechanisms
- Spiro compounds
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry