Kinetic and theoretical studies of a facile, one-pot preparation of a spirocyclohexylindolinone derivative

Andrea Sánta-Csutor, Zoltán Mucsi, Zoltán Finta, Csaba Gönczi, Judit Halász, Éva Csikós, István Hermecz

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6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1769-1778
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
Publication statusPublished - Mar 27 2006

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Keywords

  • Density functional calculations
  • Kinetics
  • Michael addition
  • Reaction mechanisms
  • Spiro compounds

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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