Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 17
207
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Unexpected Reaction of Oximinoacetoacetate with Amines: A Novel Synthesis of Carbamates

Pages 3010-3015 | Received 06 Oct 2008, Published online: 03 Aug 2009

REFERENCES

  • Edlind , T. D. ; Hang Tu , L. ; Chakraborty , P. R. Activity of the anthelmintic benzimidazoles against Giardia Lamblia in vitro . J. Infect. Dis. 1990 , 162 , 1408 .
  • Cruz , M. C. ; Bartlett , M. S. ; Edlind , T. D. In vitro susceptibility of the opportunistic fungus Cryptococcus neoformans to anthelmintic benzimidazoles . Antimicrob. Agents Chemother. 1994 , 38 , 378 – 380 .
  • Adams , P. ; Baron , F. A. Physiological properties and industrial uses of carbamates. Chem. Rev. 1965, 65 (5), 567–602.
  • Chong , P. Y. ; Janicki , S. Z. ; Petillo , P. A. Multilevel selectivity in mild and high-yielding chlorosilane-induced cleavage of carbamates to isocyanates . J. Org. Chem. 1998 , 63 ( 23 ), 8515 – 8521 .
  • Kato , T. ; Suzuki , K. ; Takahashi , J. ; Kamoshita , K. Negatively correlated cross-resistance between benzimidazole fungicides and methyl N-(3,5-dichlorophenyl)carbamate . J. Pesticide Sci. 1984 , 9 , 489 – 495 .
  • Herbez , V. ; Fischer , F. Macromolecular imidazole-tenside conjugates with carbamate linkage . Tetrahedron Lett. 2005 , 46 , 6797 – 6799 .
  • Bridgeman , E. ; Tomkinson , N. C. A simple method for preparation of di-, tri-, and tetrasubstituted non-symetrical ureas . Synlett 2006 , 243 – 246 .
  • Kammari , L. A. ; Plistil , L. ; Wirz , J. ; Klan , P. 2,5-Dimethylphencyl carbamate: A photoremovable protecting group for amines and amino acids . Photochem. Photobiol. Sci. 2007 , 6 , 50 – 56 .
  • Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis, , 2nd Ed. , Wiley ; New York , 1991 , 403 .
  • Yadav , J. S. ; Reddy , G. S. ; Reddy , M. M. ; Meshram , H. M. Zinc prompted simple and convenient synthesis of carbamates: An easy access for amino group protection . Tetrahedron Lett. 1998 , 39 , 3259 – 3262 .
  • Balack , D. A. ; Arndtsen , B. A. Cu-promoted coupling of imines, acid chlorides, and organoindium reagents . Org. Lett. 2006 , 8 , 1991 – 1993 .
  • Lebel , H. ; Leogane , O. Curtius rearrangement of aromatic carboxylic acids to access protected aniline and aromatic ureas . Org. Lett. 2006 , 8 , 5717 – 5720 .
  • Lebel , H. ; Leogane , O. Boc-protcted amines via a mild and efficient one-pot Curtius rearrangement . Org. Lett. 2005 , 7 , 4107 – 4110 .
  • Han , C. ; Porco , J. A. Jr. Synthesis of carbamates and ureas using Zr(IV)-catalyzed exchange process . Org. Lett. 2007 , 9 , 1517 – 1520 .
  • Curini , M. ; Epifano , F. ; Maltese , F. ; Rosati , O. Carbamate synthesis from amine and dimethyl carbonate under ytterbium triflate catalysis . Tetrahedron Lett. 2002 , 43 , 4895 – 4897 .
  • Caddick , S. ; Judd , D. B. ; Lewis , K. ; Reich , M. T. ; Williams , M. R. V. A generic approach for the catalysis reduction of nitriles . Tetrahedron 2003 , 59 , 5417 – 5423 .
  • Sun , C. ; Weinreb , S. Preparation and allylation of enamides and enecarbamates generated via iron (0) reduction of oximes and derivatives . Synthesis 2006 , 3585 – 3588 .
  • Elghamry , I. Synthesis of ethyl pyrrole-2-carboxylatees: A regioselective cyclization of enaminone under Knorr-type conditions . Synth. Commun. 2002 , 32 , 897 – 902 .
  • Elghamry , I. ; Tietze , L.-F. Linearly π-extended porphyrins: Synthesis of novel terabenzoylporphyrins . J. Heterocycl. Chem. 2005 , 42 , 503 – 508 .
  • Ramalingam , M. ; Venuvanalingam , P. ; Swaminathan , J. ; Buemi , G. Ab initio and DFT studies on conformations, hydrogen bonding, and electronic structures of glyoxalmonoxime and its methyl derivatives . Theochem , 2004 , 717 , 175 – 185 .
  • Genet , J. P. ; Pinal , C. ; Mallart , S. ; Juge , S. ; Thorimbert , S. ; Laffitte , J. A. Kinetic resolution in rhodium and rhutenium catalyzed hydrogenation of 2-acylamino-3-oxobutyrates . Tetrahedron: Asymmetry 2 1991 , 7 , 555 – 567 .
  • Org. Synth., Coll. Vol. 10 , 2004 , 549 ( 78 ), 2002 , 234 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.