1 / 10

Bucherer_Bergs

Bucherer_Bergs. Prepared By Hadeel Sobuh. TABLE OF CONTENTS. Objective Background Reaction and Mechanism Application and recent literature Conclusion references. Objective. To gain a knowledge about Bucherer_Bergs reaction & it’s application in industry and in organic synthesis.

arwen
Download Presentation

Bucherer_Bergs

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Bucherer_Bergs Prepared By Hadeel Sobuh

  2. TABLE OF CONTENTS • Objective • Background • Reaction and Mechanism • Application and recent literature • Conclusion • references

  3. Objective • To gain a knowledge about Bucherer_Bergs reaction & it’s application in industry and in organicsynthesis

  4. 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:

  5. 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.

  6. 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 Bucherer–Bergs 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)

  7. Mechanism of the Bucherer-Bergs Reaction

  8. 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:

  9. 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) doi:10.1021/cr60145a001 • ^ Ware, E. Chem. Rev.1950, 46, 403. (Review) doi:10.1021/cr60145a001 • ^ Montagne, C.; Shiers, J. J.; Shipman, M. Tetrahedron Letters2006, 47, 9207-9209. • ^ Li, J.; Li, L.; Li, T.; Li, H.; Liu, J. Ultrasonics Sonochemistry1996, 3, S141-S143. • ^ Carrington, H.C. Chem. Soc.1947, 681. • ^ Carrington, H.C.; Vasey, C.H; Waring, W.S. J. Chem. Soc.1959, 396.

  10. conclusion • It is a valuable method for preparation of Hydrations • It has more application inchemistry and in industry

More Related