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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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Presentation Transcript
table of contents
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

objectives
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.

background information
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
reaction and mechanism
Reaction and Mechanism

isocyanate

Acyleazide

Alkyl amine

The reaction of curtius rearrangement:

Schmidet reaction:

reaction and mechanism1
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

application and recent literature
Application and recent literature

Application of the Curtius Rearrangement in a Convenient Preparation :

3-Aminopyrazinecarboxylic Acid.

Methyl Ester .

curtius

rearrangement

application and recent literature1
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

recent literature
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

recent literature1
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

conclusion
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

references
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