Formation of a renewable amide, 3-acetamido-5-acetylfuran, via direct conversion of N-acetyl-D-glucosamine

被引:107
作者
Drover, Marcus W. [1 ]
Omari, Khaled W. [1 ]
Murphy, Jennifer N. [1 ]
Kerton, Francesca M. [1 ]
机构
[1] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
PROXIMICIN-A; ACETYLGLUCOSAMINE;
D O I
10.1039/c2ra20578e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An effective method for transforming an amino-sugar into an N-substituted furan in an ionic liquid is reported. B(OH)(3) significantly improves the yield (60%, 3 min MW heating).
引用
收藏
页码:4642 / 4644
页数:3
相关论文
共 19 条
[1]   Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals [J].
Binder, Joseph B. ;
Raines, Ronald T. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) :1979-1985
[2]   Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited [J].
Bozell, Joseph J. ;
Petersen, Gene R. .
GREEN CHEMISTRY, 2010, 12 (04) :539-554
[3]   Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone [J].
Buntara, Teddy ;
Noel, Sebastien ;
Phua, Pim Huat ;
Melian-Cabrera, Ignacio ;
de Vries, Johannes G. ;
Heeres, Hero J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) :7083-7087
[4]   Conversion of hexose into 5-hydroxymethylfurfural in imidazolium ionic liquids with and without a catalyst [J].
Cao, Quan ;
Guo, Xingcui ;
Yao, Shengxi ;
Guan, Jing ;
Wang, Xiaoyan ;
Mu, Xindong ;
Zhang, Dongke .
CARBOHYDRATE RESEARCH, 2011, 346 (07) :956-959
[5]  
Changzhi L., 2009, TETRAHEDRON LETT, V50, P5403
[6]  
Changzhi L., 2011, BIOMASS BIOENERG, V35, P2013
[7]   Volatile compounds generated from thermal degradation of N-acetylglucosamine [J].
Chen, JH ;
Wang, MF ;
Ho, CT .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (08) :3207-3209
[8]   ACETAMIDOFURANS, ACETAMIDOPYRONES, AND ACETAMIDOACETALDEHYDE FROM PYROLYSIS OF CHITIN AND N-ACETYLGLUCOSAMINE [J].
FRANICH, RA ;
GOODIN, SJ ;
WILKINS, AL .
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 1984, 7 (1-2) :91-100
[9]   Synergy of boric acid and added salts in the catalytic dehydration of hexoses to 5-hydroxymethylfurfural in water [J].
Hansen, Thomas S. ;
Mielby, Jerrik ;
Riisager, Anders .
GREEN CHEMISTRY, 2011, 13 (01) :109-114
[10]   Microwave-assisted asymmetric organocatalysis. A probe for nonthermal microwave effects and the concept of simultaneous cooling [J].
Hosseini, Masood ;
Stiasni, Nikola ;
Barbieri, Vera ;
Kappe, C. Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1417-1424