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Curtius Rearrangement

Curtius Rearrangement. Doha Dradi . Table of Contents. Slide1:The reaction name and my name Slide2:table of contant Slide3:objective of presentation Slide4:background of curtius rearrangement Slide5 +6:reaction and mechanism Slide7 8+9+10:Application and recent literature

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Curtius Rearrangement

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  1. Curtius Rearrangement Doha Dradi

  2. Table of Contents Slide1:The reaction name and my name Slide2:table of contant Slide3:objective of presentation Slide4:background of curtius rearrangement Slide5 +6:reaction and mechanism Slide7 8+9+10:Application and recent literature Slide11:Conclusion Slide12:References

  3. Objectives The basic reason of this presentation is to increase self-gums. The second reason is to Education and training students how to lay down their lectures in front of their students. Special reason for me it increased my knowledge of the interaction for the search for it. It has been shown to me, because he is in too much of the preparation of organic compound.

  4. Background Information The Curtius Rearrangement is the thermal decomposition of carboxylic azides to produce an isocyanate. These intermediates may be isolated, or their corresponding reaction or hydrolysis products may be obtained. The reaction sequence - including subsequent reaction with water which leads to amines - is named the Curtius Reaction. This reaction is similar to the Schmidt Reaction with acids, differing in that the acyl azide in the present case is prepared from the acyl halide and an azide salt. • The Curtius rearrangement (or Curtius reaction or Curtius degradation), as first defined by Theodor Curtius, is a chemical reaction that involves the rearrangement of an acyl azide to an isocyanate.Several reviews have been published

  5. Reaction and Mechanism isocyanate Acyleazide Alkyl amine The reaction of curtius rearrangement: Schmidet reaction:

  6. Reaction and Mechanism Mechanism of the Curtius Rearrangement Preparation of azides: Decomposition: Reaction with water to the unstable carbamic acid derivative which will undergo spontaneous decarboxylation: Isocyanates are versatile starting materials: Isocyanates are also of high interest as monomers for polymerization work and in the derivatisation of biomacromoleculesScope

  7. Application and recent literature Application of the Curtius Rearrangement in a Convenient Preparation : 3-Aminopyrazinecarboxylic Acid. Methyl Ester . curtius rearrangement

  8. Application and recent literature Recent Literature Boc-Protected Amines via a Mild and Efficient One-Pot Curtius RearrangementH. Lebel, O. Leogane, Org. Lett., 2005, 7, 4107-4110 Carboxylic acid Tert-butyle methyl carbonate One-Pot Synthesis of Ureido Peptides and Urea-Tethered Glycosylated Amino Acids Employing Deoxo-Fluor and TMSN3H. P. Hemantha, G. Chennakrishnareddy, T. M. Vishwanatha, V. V. Sureshbabu, Synlett, 2009, 407-410

  9. Recent literature Radical Azidonation of AldehydesL. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem., 2003, 68, 9453-9455 Acyleazid Isocyanate Iodobenzene Dichloride in Combination with Sodium Azide for the Effective Synthesis of Carbamoyl Azides from AldehydesX.-Q. Li, X.-F. Zhao, C. Zhang, Synthesis, 2008, 2589-2593. Acylecarbamoylazide aldahyde

  10. Recent literature Radical Azidonation of AldehydesL. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem., 2003, 68, 9453-9455 An Efficient Synthesis of a Probe for Prot einFunction: 2,3-Diaminopropionic Acid with Orthogonal Protecting GroupsE. A. Englund, H. N. Gopi, D. H. Appella, Org. Lett., 2004, 6, 213-215. 3-bis(tert-butoxycarbonyl)amino-4-methoxy-4-oxobutanoic Methyl-2-(bis(tert-butoxycarbonyl)amino)-3-isocyanatopropanoate Ethylcarbonochloridate

  11. Conclusion In summary , the curtius rearrangement is very important to prepare many compound like 3-Aminopyrazinecarboxylic Acid, Methyl Ester , and this need sum reaction ,and sum steps to do this. we have some new and old Recent literature of my reaction, and some application. In the end I hope that I have brought you the knowledge and the wealth of information about

  12. References ^ Lebel, H.; Leogane, O. (2005). "Boc-protected amines via a mild and efficient one-pot Curtius rearrangement". Organic letters7 (19): 4107–4110. doi:10.1021/ol051428b. PMID16146363.  edit ^ Shioiri, T.; Yamada, S. (1990), "Diphenyl phosphorazidate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv7p0206 ; Coll. Vol.7: 206  ^ Shioiri, T.; Ninomiya, K.; Yamada, S. (1972). "Diphenylphosphoryl azide. New convenient reagent for a modified Curtius reaction and for peptide synthesis". Journal of the American Chemical Society94 (17): 6203. doi:10.1021/ja00772a052. PMID5054412.  edit ^ Ninomiya, K. (1974). "Phosphorus in organic synthesis—VII , Diphenyl phosphorazidate (DPPA). A new convenient reagent for a modified curtius reaction". Tetrahedron30 (14): 2151–2157. doi:10.1016/S0040-4020(01)97352-1.  edit ^ Jessup, P. J.; Petty, C. B.; Roos, J.; Overman, L. E. (1988), "1-N-Acylamino-1,3-dienes from 2,4-pentadienoic acids by the Curtius rearrangement: benzyl trans-1,3-butadiene-1-carbamate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0095 ; Coll. Vol.6: 95  ^ Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). Hoboken, New Jersey: Wiley. p. 1609. ISBN9780471720911.  ^http://www.chempensoftware.com/reactions/RXN051.htm

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