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Nucleophile-intercepted Beckmann fragmentation reactions.

Samuel J Touchette1, Evan M Dunkley1, Leah L Lowder1

  • 1Department of Chemistry , Dartmouth College , Hanover , New Hampshire 03755 , USA .

Chemical Science
|October 8, 2019
PubMed
Summary
This summary is machine-generated.

This study introduces nucleophile-intercepted Beckmann fragmentation of indoline oximes, yielding cyano chlorides. This novel reaction proceeds via an aziridinium intermediate and can be adapted for various nucleophiles.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • The Beckmann fragmentation is a key reaction in organic synthesis.
  • Indoline alkaloids, such as akuammiline and koumine, possess significant biological activities.
  • Developing efficient synthetic routes to complex alkaloids is crucial for drug discovery.

Purpose of the Study:

  • To report the first examples of nucleophile-intercepted Beckmann fragmentations of indoline oximes.
  • To explore the mechanism and scope of this novel reaction.
  • To demonstrate the utility of the resulting products in alkaloid synthesis.

Main Methods:

  • Utilizing MsCl (methanesulfonyl chloride) as a promoter for the fragmentation of indoline oximes.
  • Investigating the reaction mechanism, including the proposed aziridinium intermediate.
  • Employing various nucleophiles (oxygen, nitrogen, bromide) with different promoters to expand reaction scope.

Main Results:

  • Successfully achieved nucleophile-intercepted Beckmann fragmentation of indoline oximes for the first time.
  • Identified cyano chlorides as key products of the MsCl-promoted reaction.
  • Demonstrated the feasibility of using diverse nucleophiles and promoters for this fragmentation.

Conclusions:

  • The nucleophile-intercepted Beckmann fragmentation offers a novel pathway to functionalized indoline derivatives.
  • The reaction proceeds via a double stereoinvertive aziridinium intermediate.
  • The synthesized products hold potential for the efficient construction of akuammiline and koumine alkaloid frameworks.