Bucherer_Bergs

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Bucherer_Bergs

• Prepared By Hadeel Sobuh

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TABLE OF CONTENTS

• Objective
• Background
• Reaction and Mechanism
• Application and recent literature
• Conclusion
• references

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Objective

• To gain a knowledge about Bucherer_Bergs reaction
  its application in industry and in organic
  synthesis

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Background

• A multi-component reaction between a ketone,
  potassium cyanide and ammonium carbonate, which
  leads to the formation of hydantoins.
• A pre-formed cyanohydrin can react with ammonium
  carbonate to give the same product

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Application and recent literature

• Recent Literature
• Spiro Hydantoin Aldose Reductase Inhibitors
  Derived from 8-Aza-4-chromanonesR. Sarges, S. W.
  Goldstein, W. M. Welch, J. Med. Chem., 1990, 33,
  1859-1865.

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Application and recent literature

• Modified Bucherer-Bergs Reaction for the One-Pot
  Synthesis of 5,5'-Disubstituted Hydantoins from
  Nitriles and Organometallic ReagentsC. Montagne,
  M. Shipman, Synlett, 2006, 2203-2206.
• The hydantoins formed by the BuchererBergs
  reaction have many useful applications. They
• are useful in carbohydrate chemistry.
• are important heterocyclic scaffolds that induce
  biological effects.
• are useful precursors to non-natural amino acids.
  
• have pharmacological importance (ex.
  5,5-diphenylhydantoin, also known as Dilantin)

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Mechanism of the Bucherer-Bergs Reaction
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Mechanism of the Bucherer-Bergs Reaction

• The Bucherer-Bergs Reaction is equivalent to the
  Strecker Synthesis with "additional CO2".
  Hydantoins may be opened to yield
  N-carbamoylamino acids which form amino acids by
  treatment with acid or with a suitable enzyme

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References

• Bucherer, H. T. Fischbeck, H. T. J. Prakt.
  Chem. 1934, 140, 69.
• Bucherer, H. T. Steiner, W. J. Prakt. Chem.
  1934, 140, 291.
• Bergs, H. Ger. pat. 566,094 (1929).
• Ware, E. Chem. Rev. 1950, 46, 403. (Review)
  doi10.1021/cr60145a001
• Ware, E. Chem. Rev. 1950, 46, 403. (Review)
  doi10.1021/cr60145a001
• Montagne, C. Shiers, J. J. Shipman, M.
  Tetrahedron Letters 2006, 47, 9207-9209.
• Li, J. Li, L. Li, T. Li, H. Liu, J.
  Ultrasonics Sonochemistry 1996, 3, S141-S143.
• Carrington, H.C. Chem. Soc. 1947, 681.
• Carrington, H.C. Vasey, C.H Waring, W.S. J.
  Chem. Soc. 1959, 396.

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conclusion

• It is a valuable method for preparation of
  Hydrations

• It has more application in chemistry and in
  industry