Mild and eco-friendly chemoselective acylation of amines in aqueous medium

被引:35
作者
Naik, S [1 ]
Bhattacharjya, G [1 ]
Kavala, VR [1 ]
Patel, BK [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, India
关键词
amines; amides; acylation; anhydrides; aqueous medium; chemoselective;
D O I
10.3998/ark.5550190.0005.104
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amines in the form of amine hydrochlorides are efficiently acylated with anhydrides in an aqueous medium on addition of NaHCO3. Both cyclic and acyclic anhydrides react with equal ease with an amine and amines of various stereo-electronic factors react with the same rates with an anhydride. No chromatographic separation is needed for isolation of the acylated product. Reactions in aqueous medium, innocuous by-products and chemoselective acylation of amines in the presence of phenols and thiols have been achieved with high selectivity.
引用
收藏
页码:55 / 63
页数:9
相关论文
共 44 条
[1]   Per-O-acetylation of sugars catalysed by montmorillonite K-10 [J].
Bhaskar, PM ;
Loganathan, D .
TETRAHEDRON LETTERS, 1998, 39 (15) :2215-2218
[2]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[3]  
Chauhan KK, 1999, SYNLETT, P1743
[4]   Catalytic acetylation of alcohols, phenols, thiols and amines with zeolite H-FER under solventless conditions [J].
Chavan, SP ;
Anand, R ;
Pasupathy, K ;
Rao, BS .
GREEN CHEMISTRY, 2001, 3 (06) :320-322
[5]   Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate [J].
Chen, CT ;
Kuo, JH ;
Li, CH ;
Barhate, NB ;
Hon, SW ;
Li, TW ;
Chao, SD ;
Liu, CC ;
Li, YC ;
Chang, IH ;
Lin, JS ;
Liu, CJ ;
Chou, YC .
ORGANIC LETTERS, 2001, 3 (23) :3729-3732
[6]   THE PREPARATION OF PURE N-ACETYL-L-LEUCINE AND L-LEUCINE [J].
DEWITT, HD ;
INGERSOLL, AW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (07) :3359-3360
[7]  
DSa BA, 1996, J ORG CHEM, V61, P2963
[8]  
Furniss B.S., 1989, VOGELS TXB PRACTICAL, V4th
[9]   Peroxovanadium-catalyzed oxidative esterification of aldehydes [J].
Gopinath, R ;
Barkakaty, B ;
Talukdar, B ;
Patel, BK .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2944-2947
[10]   Tetrabutylammonium tribromide (TBATB) as an efficient generator of HBr for an efficient chemoselective reagent for acetalization of carbonyl compounds [J].
Gopinath, R ;
Haque, SJ ;
Patel, BK .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5842-5845