Kinetic and Theoretical Studies of a Facile, One‐Pot Preparation of a Spirocyclohexylindolinone Derivative

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, multicomponent 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Hydrothermal treatments of two cowpea (Vigna unguiculata L. Walp) varieties: effect of micronisation on physicochemical and structural characteristics

“…As a result, the spirocyclic compound 1 became available through a novel protocol, based on latest radical chemistry of aromatic azides, which, besides providing a strongly enhanced yield of 1 , employs a more convenient azido precursor and also results in highly minimized atom waste. Furthermore, this protocol compares favourably even with other reported non‐radical methods 1b,c,4–6…”

One‐Pot Triple and Mixed Double Michael Addition of Activated Alkenes to 2‐Oxindole and 7‐Aza‐2‐Oxindole: Synthesis of C‐3/N‐Functionalized Carbon Rich 2‐Oxindole and 7‐Aza‐2‐Oxindole Derivatives

“…Recently, we have explored the synthetic use of 7‐aza‐2‐indolone for the construction of spiro and heterocyclic compounds via the Azomethine ylide (AMY) and ring‐closing metathesis (RCM) strategy [12] . Triple Michael addition of 2‐oxindole and 7‐aza‐2‐indolone has been reported by Thompson et al., [13] Chande et al., [14] and Hermecz et al [15] . The main drawbacks of the published methods are 1.…”

A Divergent Synthesis of Spiropyrazole Derivatives Containing Iminolactone and/or Cyclic Imide Moiety

“…On the other hand, spirocompounds have also attracted the attention of organic and medicinal chemists because of their broad spectrum of biological activities . Hence, their synthesis continues to attract attention and provides an interesting challenge . In the literature, there is not much research related to the synthesis of spiropyrazole derivatives, even though they also have biological activities .…”