Method for the synthesis of N-alkyl-O-alkyl carbamates

被引:14
作者
Vaillard, Victoria A. [1 ]
Gonzalez, Marianela [1 ]
Perotti, Jesica P. [1 ]
Grau, Ricardo J. A. [1 ]
Vaillard, Santiago E. [1 ]
机构
[1] UNL, CONICET, Ctr Cient Tecnol Santa Fe, Inst Desarrollo Tecnol Ind Quim INTEC, RA-3000 Santa Fe, Argentina
关键词
SOLID-PHASE SYNTHESIS; CARBAMOYLIMIDAZOLIUM; PROTOCOL; REAGENTS; EFFICIENT; ALCOHOLS; AMIDES; UREAS; SALTS;
D O I
10.1039/c4ra00373j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Primary and secondary carbamates were prepared from primary, secondary and neo-pentyl alcohols, and carbonyl-di-imidazole (CDI), using a new three step method. Non-acidic alcohols reacted with CDI affording carbamoyl-imidazoles with excellent yields (92-97%). The carbamoyl-imidazoles were then converted into the more reactive imidazolium salts, which upon reaction with primary and secondary amines afforded the corresponding carbamates in high isolated yields (66-99%).
引用
收藏
页码:13012 / 13017
页数:6
相关论文
共 26 条
[1]   ESTERS OF CARBAMIC ACID [J].
ADAMS, P ;
BARON, FA .
CHEMICAL REVIEWS, 1965, 65 (05) :567-&
[2]   An efficient new protocol for the formation of unsymmetrical tri- and tetrasubstituted ureas [J].
Batey, RA ;
Santhakumar, V ;
Yoshina-Ishii, C ;
Taylor, SD .
TETRAHEDRON LETTERS, 1998, 39 (35) :6267-6270
[3]   A new protocol for the formation of carbamates and thiocarbamates using carbamoyl imidazolium salts [J].
Batey, RA ;
Yoshina-Ishii, C ;
Taylor, SD ;
Santhakumar, V .
TETRAHEDRON LETTERS, 1999, 40 (14) :2669-2672
[4]  
BERNTSSON P, 1977, ACTA PHARM SUEC, V14, P229
[5]   A new simple one-pot regioselective preparation of mixed diesters of carbonic acid [J].
Bertolini, G ;
Pavich, G ;
Vergani, B .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :6031-6034
[6]   Solid phase synthesis of oxazolidinones via a novel cyclisation/cleavage reaction [J].
Buchstaller, HP .
TETRAHEDRON, 1998, 54 (14) :3465-3470
[7]  
Chaturvedi D., 2013, ROLE ORGANIC CARBAMA
[8]  
Chaturvedi D, 2007, CURR ORG SYNTH, V4, P310
[9]   Perspectives on the synthesis of organic carbamates [J].
Chaturvedi, Devdutt .
TETRAHEDRON, 2012, 68 (01) :15-45
[10]  
Cotarca L, 1996, SYNTHESIS-STUTTGART, P553