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

Synthetic Communications

Volumn 39, Issue 17, 2009, Pages 3010-3015

  Elghamry, Ibrahim ^a,b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b Misr International University   (Egypt)

Author keywords

Carbamate synthesis; Keto enol tautomerization; Oxime

Indexed keywords

ACETIC ACID; ALKYL GROUP; AMINE; CARBAMIC ACID DERIVATIVE; OXIMINOACETOACETATE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 68749083536     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802564741     Document Type: Article

References (22)

1. 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.
2. 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.
3. Adams, P.; Baron, F. A. Physiological properties and industrial uses of carbamates. Chem. Rev. 1965, 65 (5), 567-602.
4. 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.
5. 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.
6. Herbez, V.; Fischer, F. Macromolecular imidazole-tenside conjugates with carbamate linkage. Tetrahedron Lett. 2005, 46, 6797-6799.
7. Bridgeman, E.; Tomkinson, N. C. A simple method for preparation of di-, tri-, and tetrasubstituted non-symetrical ureas. Synlett 2006, 243-246.
8. 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.
9. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed., Wiley; New York, 1991, 403.
10. 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.
11. Balack, D. A.; Arndtsen, B. A. Cu-promoted coupling of imines, acid chlorides, and organoindium reagents. Org. Lett. 2006, 8, 1991-1993.
12. Lebel, H.; Leogane, O. Curtius rearrangement of aromatic carboxylic acids to access protected aniline and aromatic ureas. Org. Lett. 2006, 8, 5717-5720.
13. Lebel, H.; Leogane, O. Boc-protcted amines via a mild and efficient one-pot Curtius rearrangement. Org. Lett. 2005, 7, 4107-4110.
14. Han, C.; Porco, J. A. Jr. Synthesis of carbamates and ureas using Zr(IV)catalyzed exchange process. Org. Lett. 2007, 9, 1517-1520.
15. 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.
16. 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.
17. Sun, C.; Weinreb, S. Preparation and allylation of enamides and enecarbamates generated via iron (0) reduction of oximes and derivatives. Synthesis 2006, 3585-3588.
18. Elghamry, I. Synthesis of ethyl pyrrole-2-carboxylatees: A regioselective cyclization of enaminone under Knorr-type conditions. Synth. Commun. 2002, 32, 897-902.
19. Elghamry, I.; Tietze, L.-F. Linearly π-extended porphyrins: Synthesis of novel terabenzoylporphyrins. J. Heterocycl. Chem. 2005, 42, 503-508.
20. 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.
21. 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.
22. Org. Synth., Coll. Vol. 10, 2004, 549 (78), 2002, 234.