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Gold-Catalyzed Cyclisation by 1,4-Dioxidation.

Vanessa Claus1, Lise Molinari1, Simon Büllmann1

  • 1Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

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Summary
This summary is machine-generated.

Gold catalysis enables the cyclization of amide-substituted diynes to form 1-indenones and 1-iminoindenones. This reaction generates reactive intermediates, leading to novel substituted inden-1-on-3-carboxamides.

Keywords:
cyclizationdiphenylsulfoxidediynesgoldynamides

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Amide-substituted diynes are versatile precursors in organic synthesis.
  • Gold catalysis has emerged as a powerful tool for activating alkynes and enabling complex transformations.
  • The development of efficient synthetic routes to indenone derivatives remains an active area of research.

Purpose of the Study:

  • To investigate the cyclization of amide-substituted diynes using cationic gold catalysts.
  • To explore the reactivity of the generated intermediates with external nucleophiles.
  • To synthesize novel substituted inden-1-on-3-carboxamides.

Main Methods:

  • Cyclization of amide-substituted diynes catalyzed by a cationic gold species.
  • Reaction of the intermediate ketene iminium ion with nucleophiles such as diphenyl sulfoxide and anthranil.
  • Subsequent oxidation step to yield the final products.

Main Results:

  • The gold-catalyzed cyclization successfully produced 1-indenones and 1-iminoindenones.
  • The electron-donating nitrogen atom facilitated the formation of a reactive ketene iminium ion intermediate.
  • Trapping of the intermediate with diphenyl sulfoxide or anthranil, followed by oxidation, afforded substituted inden-1-on-3-carboxamides.

Conclusions:

  • Cationic gold catalysis provides an effective strategy for the synthesis of 1-indenones and 1-iminoindenones from amide-substituted diynes.
  • The reaction proceeds via a ketene iminium ion intermediate, which can be intercepted by nucleophiles.
  • This methodology offers a new route to diverse inden-1-on-3-carboxamide derivatives.