Versatile Use of Carbon Dioxide in the Synthesis of Carbamates

Summary.Organic carbamates classically have been synthesized using harmful and toxic reagents like phosgene, its derivatives, and carbon monoxide. Recently, carbon dioxide was used as a cheap and harmless reagent for the synthesis of organic carbamates in the gaseous or supercritical state, or in an electrochemical process, or organic carbonates as sources of carbon dioxide as an alternative to the harmful reagents. The present review will deal with the extensive use of carbon dioxide in the synthesis of organic carbamates.

[1]  E. Duñach,et al.  Electrosynthesis of cyclic carbamates from aziridines and carbon dioxide , 2000 .

[2]  J. Mayer,et al.  Solid phase synthesis of quinazolinones , 1997 .

[3]  Yeon Joo Jung,et al.  Chemoselective conversion of azides to t-butyl carbamates and amines , 2002 .

[4]  D. Satchell,et al.  Acylation by ketens and isocyanates. A mechanistic comparison , 1975 .

[5]  Y. Yoshida,et al.  Synthesis of carbamic ester by a reaction of carbon dioxide, tetrakis(dimethylamido)titanium(IV) and epoxide. , 1978 .

[6]  C. Bruneau,et al.  Catalytic synthesis of vinyl carbamates from carbon dioxide and alkynes with ruthenium complexes , 1989 .

[7]  D. Chaturvedi,et al.  Application of organic carbamates in drug design. Part 1:anticancer agents - recent reports , 2004 .

[8]  Arun K. Ghosh,et al.  N,N'-Disuccinimidyl Carbonate: A Useful Reagent for Alkoxycarbonylation of Amines. , 1992, Tetrahedron letters.

[9]  Masaaki Yoshida,et al.  Catalytic production of urethanes from amines and alkyl halides in supercritical carbon dioxide , 2000 .

[10]  J. E. Lyons,et al.  Catalysis research of relevance to carbon management: progress, challenges, and opportunities. , 2001, Chemical reviews.

[11]  D. Riley,et al.  Palladium-catalyzed generation of O-allylic urethanes and carbonates from amines/alcohols, carbon dioxide, and allylic chlorides , 1993 .

[12]  T. Endo,et al.  Reaction of Various Oxiranes and Carbon Dioxide. Synthesis and Aminolysis of Five-Membered Cyclic Carbonates , 2000 .

[13]  M. Lemaire,et al.  An environmentally benign access to carbamates and ureas , 2000 .

[14]  T. Toda REACTIONS OF CARBON DIOXIDE WITH α-BROMOACYLOPHENONES: FORMATION OF OXAZOLIDONE DERIVATIVES , 1977 .

[15]  P. Adams,et al.  Esters of Carbamic Acid , 1965 .

[16]  M. Aresta,et al.  Mechanistic studies on the role of carbon dioxide in the synthesis of methylcarbamates from amines and dimethylcarbonate in the Presence of CO2. , 1991 .

[17]  Arun K. Ghosh,et al.  An Efficient Synthesis of Functionalized Urethanes from Azides. , 1992, Journal of the Chemical Society. Chemical communications.

[18]  S. Chandrasekhar,et al.  Direct Conversion of Azides and Benzyl Carbamates to t-Butyl Carbamates Using Polymethylhydrosiloxane and Pd-C , 2000 .

[19]  D. S. Jones,et al.  A Convenient Method for the Conversion of Amines to Carbamates , 1985 .

[20]  Yi Pan,et al.  Carbon Dioxide as a Phosgene Replacement: Synthesis and Mechanistic Studies of Urethanes from Amines, CO2, and Alkyl Chlorides , 1995 .

[21]  J. Sinisterra,et al.  Enzymatic Amidation and Alkoxycarbonylation of Amines using Native and Immobilised Lipases with Different Origins: a Comparative Study , 2000 .

[22]  S. Chandrasekhar,et al.  Single-step conversion of N-benzyl, N-trityl and N-diphenylmethyl amines to t-butyl carbamates using polymethylhydrosiloxane , 2003 .

[23]  K. Tominaga,et al.  Synthesis of 2-Oxazolidinones from CO2 and 1,2-Aminoalcohols Catalyzed by n-Bu2SnO , 2002 .

[24]  T. Aida,et al.  Fixation and activation of carbon dioxide on aluminum porphyrin. Catalytic formation of a carbamic ester from carbon dioxide, amine, and epoxide. , 1986, Journal of the American Chemical Society.

[25]  A. Gennaro,et al.  Synthesis of chiral oxazolidin-2-ones by 1,2-amino alcohols, carbon dioxide and electrogenerated acetonitrile anion , 2002 .

[26]  Victor Snieckus,et al.  Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics , 1990 .

[27]  H. Takimizu,et al.  Structure-activity study of L-cysteine-based N-type calcium channel blockers: optimization of N- and C-terminal substituents. , 2002, Bioorganic & medicinal chemistry letters.

[28]  YoshidaYasuhiko,et al.  A DIRECT SYNTHESIS OF MONOCARBAMIC ESTER OF 1,2-DIOL FROM CARBON DIOXIDE, EPOXIDE AND AMINE , 1978 .

[29]  P. Dixneuf,et al.  Ruthenium catalysed regioselective synthesis of O-1-(1,3-dienyl) carbamates directly from CO2 , 1991 .

[30]  M. Watanabe,et al.  Novel Synthesis of Carbamate Ester from Carbon Dioxide, Amines, and Alkyl Halides , 1989 .

[31]  T. Sakakura,et al.  Halogen-free process for the conversion of carbon dioxide to urethanes by homogeneous catalysis. , 2001, Chemical communications.

[32]  Youquan Deng,et al.  The syntheses of carbamates from reactions of primary and secondary aliphatic amines with dimethyl carbonate in ionic liquids , 2002 .

[33]  Atul Kumar,et al.  A high yielding one-pot, novel synthesis of carbamate esters from alcohols using Mitsunobu's reagent , 2003 .

[34]  L. Rossi,et al.  Electrochemical activation of carbon dioxide: synthesis of carbamates , 1996 .

[35]  Richard M. Cross,et al.  ChemInform Abstract: Efficient Cs2CO3-Promoted Solution and Solid Phase Synthesis of Carbonates and Carbamates in the Presence of TBAI. , 2002 .

[36]  K. W. Jung,et al.  An efficient one-pot synthesis of N-alkyl carbamates from primary amines using Cs2CO3 , 2001 .

[37]  T. Tsuda,et al.  Preparation of urethanes from carbon dioxide via a copper(I) carbamato-complex , 1978 .

[38]  H. Ohno,et al.  Highly potent inhibitors of TNF-α production. Part 2: Identification of drug candidates , 2002 .

[39]  M. Curini,et al.  Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis , 2002 .

[40]  T. Asano,et al.  Formation of bis(2-oxazolidinone) derivatives by reactions of 2-methoxy-3,3-dimethyl-2-phenyloxirane or α-bromoisobutyrophenone with carbon dioxide and aliphatic α,ω-diamines , 1986 .

[41]  L. Rossi,et al.  ELECTROGENERATED SUPEROXIDE-ACTIVATED CARBON DIOXIDE. A NEW MILD AND SAFE APPROACH TO ORGANIC CARBAMATES , 1997 .

[42]  S. R. Pathak,et al.  Organic carbamates in drug development. Part II: antimicrobial agents - recent reports , 2005 .

[43]  P. Dixneuf,et al.  A novel catlytic synthesis of vinyl carboamtes from carbon dioxide, diethylamine, and alkynes in the presence of Ru3(CO)12 , 1986 .

[44]  R. V. Chaudhari,et al.  Carbamate synthesis by solid-base catalyzed reaction of disubstituted ureas and carbonates , 2001 .

[45]  H. Okuno,et al.  Formation of cyclic urethanes from amino alcohols and carbon dioxide using phosphorus(III) reagents and halogenoalkanes , 1993 .

[46]  K. Butcher Carbamate esters: a simple, mild method of formation , 1994 .

[47]  Y. Yoshida,et al.  Novel Synthesis of Carbamic Ester from Carbon Dioxide, Amine, and Ortho Ester , 1989 .

[48]  B. Dombek,et al.  Oxidative carbonylation of amines catalysed by metallomacrocyclic compounds , 1992 .

[49]  V. Gotor,et al.  Chemo-enzymatic synthesis of 2′-deoxynucleoside urethanes , 1993 .

[50]  A. Perosa,et al.  The synthesis of alkyl carbamates from primary aliphatic amines and dialkyl carbonates in supercritical carbon dioxide , 2002 .

[51]  D. W. Franco,et al.  Efficient and clean synthesis of N-alkyl carbamates by transcarboxylation and O-alkylation coupled reactions using a DBU–CO2 zwitterionic carbamic complex in aprotic polar media , 2002 .

[52]  Michele Aresta,et al.  Role of the macrocyclic polyether in the synthesis of N-alkylcarbamate esters from primary amines, CO2 and alkyl halides in the presence of crown-ethers. , 1992 .

[53]  M. Moore,et al.  Reactions of aralkyl amines with carbon dioxide. , 1948, Journal of the American Chemical Society.

[54]  T. Asano,et al.  FORMATION OF CARBAMATE DERIVATIVES BY REACTION OF CHLOROMETHYLOXIRANE OR PHENYLOXIRANE WITH CARBON DIOXIDE AND ALIPHATIC AMINES , 1978 .

[55]  Michele Aresta,et al.  Biomimetic building-up of the carbamic moiety: the intermediacy of carboxyphosphate analogues in the synthesis of N-aryl carbamate esters from arylamines and organic carbonates promoted by phosphorus acids , 1995 .

[56]  J. R. Hanson,et al.  Protecting Groups in Organic Synthesis , 1999 .

[57]  Atul Kumar,et al.  AN EFFICIENT ONE POT SYNTHESIS OF CARBAMATE ESTERS THROUGH ALCOHOLIC TOSYLATES* , 2002 .

[58]  K. W. Jung,et al.  Cs(2)CO(3)-promoted efficient carbonate and carbamate synthesis on solid phase. , 2000, Organic letters.