Green and Practical Synthesis of Carbamates from Ureas and Organic Carbonates

REFERENCES

• (a) Buchstaller , H. P. Solid phase synthesis of oxazolidinones via a novel cyclisation/cleavage reaction . Tetrahedron 1998 , 54 , 3465 – 3470 ; (b) Holte , P. ; Thijs , L. ; Zwanenburg , B. Chiral recognition of tartaric acid derivatives with chromenone-benzoxazole receptors and a spirobifluorene spacer . Tetrahedron Lett. 1998 , 39 , 7404 – 7410 ; (c) Sasse , A. ; Stark , H. ; Ligneau , X. ; Elz , S. ; Reidemeister , S. ; Ganellin , C. R. ; Schwartz , J. C. ; Schunack , W. (Partial) agonist/antagonist properties of novel diarylalkyl carbamates on histamine H3 receptors . Bioorg. Med. Chem. 2000 , 8 , 1139 – 1149 ; (d) Karki , R. G. ; Kulkarni , V. M. Three-dimensional quantitative structure–activity relationship (3D-QSAR) of 3-aryloxazolidin-2-one antibacterials . Bioorg. Med. Chem. 2001 , 9 , 3153 – 3160 ; (e) Yu , D. ; Huiyuan , G. Synthesis and antibacterial activity of linezolid analogues . Bioorg. Med. Chem. Lett. 2002 , 12 , 857 – 859 .
   Web of Science ®Google Scholar
• (a) McGhee , W. D. ; Riley , D. P. Palladium-mediated synthesis of urethanes from amines, carbon dioxide, and cyclic diolefins . Organometallics 1992 , 11 , 900 – 907 ; (b) Valli , V. L. K. ; Alper , H. A simple, convenient, and efficient method for the synthesis of isocyanates from urethanes . J. Org. Chem. 1995 , 60 , 257 – 258 .
   Google Scholar
• (a) Norwick , J. S. ; Powell , N. A. ; Nguyen , T. M. ; Noronha , G. An improved method for the synthesis of enantiomerically pure amino acid ester isocyanates . J. Org. Chem. 1992 , 57 , 7364 – 7366 ; (b) Majer , P. ; Randad , R. A safe and efficient method for preparation of N,N′-unsymmetrically disubstituted ureas utilizing triphosgene . J. Org. Chem. 1994 , 59 , 1937 – 1938 .
   Google Scholar
• (a) Baba , T. ; Kobayashi , A. ; Kawanami , Y. ; Inazu , K. ; Ishikawa , A. ; Echizenn , T. ; Murai , K. ; Aso , S. ; Inomata , M. Characteristics of methoxycarbonylation of aromatic diamine with dimethyl carbonate to dicarbamate using a zinc acetate catalyst . Green Chem. 2005 , 7 , 159 – 165 ; (b) Baba , T. ; Fujiwara , M. ; Oosaku , A. ; Kobayashi , A. ; Deleon , R. G. ; Ono , Y. Catalytic synthesis of N-alkyl carbamates by methoxycarbonylation of alkylamines with dimethyl carbonate using Pb(NO3)2 . Appl. Catal. A: Gen. 2002 , 227 , 1 .
   Google Scholar
• (a) Gupte , S. P. ; Shivarkar , A. B. ; Chaudhari , R. V. Carbamate synthesis by solid-base-catalyzed reaction of disubstituted ureas and carbonates. Chem. Commun. 2001, 2620–2621; (b) Gao , J. ; Li , H. ; Zhang , Y. F. ; Zhang , Y. A nonphosgene route for synthesis of methyl N-phenyl carbamate derived from CO2 under mild conditions. Green Chem. 2007, 9, 572–576; (c) Shivarkar , A. B. ; Gupte , S. P. ; Chaudhari , R. V. Carbamate synthesis via transfunctionalization of substituted ureas and carbonates. J. Mol. Catal. A: Chem. 2004, 223, 85–92.
   Google Scholar
• (a) Abla , M. ; Choi , J. ; Sakakura , T. Halogen-free process for the conversion of carbon dioxide to urethanes by homogeneous catalysis . Chem. Commun. 2001 , 2238 – 2239 ; (b) Shi , F. ; Deng , Y. ; Sima , T. ; Peng , J. ; Gu , Y. ; Qiao , B. Alternatives to phosgene and carbon monoxide: Synthesis of symmetric urea derivatives with carbon dioxide in ionic liquids . Angew. Chem. Int. Ed. 2003 , 42 , 3257 – 3260 ; (c) Bhanage , B. M. ; Fujita , S. ; Ikushima , Y. ; Arai , M. Synthesis of cyclic ureas and urethanes from alkylene diamines and amino alcohols with pressurized carbon dioxide in the absence of catalysts . Green Chem. 2003 , 5 , 340 – 342 ; (d) Ion , A. ; Parvulescu , V. ; Jacobs , P. ; Vos , D. D. Synthesis of symmetrical or asymmetrical urea compounds from CO2 via base catalysis . Green Chem. 2007 , 9 , 158 – 161 .
   Google Scholar
• (a) Dunn , B. C. ; Guenneau , C. ; Hilton , S. A. ; Pahnke , J. ; Eyring , E. M. Production of diethyl carbonate from ethanol and carbon monoxide over a heterogeneous catalyst . Energy Fuels 2002 , 16 , 177 – 181 ; (b) Okuyama , K. ; Sugiyama , J. ; Nagahata , R. ; Asai , M. ; Ueda , M. ; Takeuchi , K. An environmentally benign process for aromatic polycarbonate synthesis by efficient oxidative carbonylation catalyzed by Pd-carbene complexes . Green Chem. 2003 , 5 , 563 – 566 ; (c) Zhang , Z. ; Ma , X. B. ; Zhang , J. ; He , F. ; Wang , S. P. Effect of crystal structure of copper species on the rate and selectivity in oxidative carbonylation of ethanol for diethyl carbonate synthesis . J. Mol. Catal. A: Chem. 2005 , 227 , 141 – 146 .
   Web of Science ®Google Scholar
• (a) Shi , F. ; Deng , Y. ; Sima , T. ; Yang , H. A novel PdCl2/ZrO2– catalyst for synthesis of carbamates by oxidative carbonylation of amines . J. Catal. 2001 , 203 , 525 – 528 ; (b) Shi , F. ; Zhang , Q. ; Gu , Y. ; Deng , Y. Silica gel confined ionic liquid–metal complexes for oxygen-free carbonylation of amines and nitrobenzene to ureas . Adv. Synth. Catal. 2005 , 347 , 225 – 230 .
   Google Scholar
• (a) Selva , M. ; Bomben , A. ; Tundo , P. Selective mono-N-methylation of primary aromatic amines by dimethyl carbonate over faujasite X- and Y-type zeolites . J. Chem. Soc., Perkin Trans. 1 1997 , 1041 – 1045 ; (b) Selvam , M. ; Tundo , P. Selective N-methylation of primary aliphatic amines with dimethyl carbonate in the presence of alkali cation exchanged Y-faujasites . Tetrahedron Lett. 2003 , 44 , 8139 – 8142 ; (c) Tundo , P. ; Selva , M. The chemistry of dimethyl carbonate . Acc. Chem. Res. 2002 , 35 , 706 – 716 .
   Google Scholar