Deprotection of N-tosylated indoles and related structures using cesium carbonate

被引:66
作者
Bajwa, Joginder S. [1 ]
Chen, Guang-Pei [1 ]
Prasad, Kapa [1 ]
Repic, Jan [1 ]
Blacklock, Thomas J. [1 ]
机构
[1] Nova Pharmaceut Corp, Proc R&D Chem & Analyt Dev, E Hanover, NJ 07936 USA
关键词
N-detosylation; azaindoles; indoles; imidazoles; cesium carbonate;
D O I
10.1016/j.tetlet.2006.06.132
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A very mild, efficient, and convenient method for deprotection of N-tosylated indoles and related structures by cesium carbonate in THF-MeOH is described. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6425 / 6427
页数:3
相关论文
共 15 条
[1]  
[Anonymous], 2003, PROTECTIVE GROUPS
[2]   EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].
BORDWELL, FG .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463
[3]   Cleavage of sulfonamides with phenyldimethylsilyllithium [J].
Fleming, I ;
Frackenpohl, J ;
Ila, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (07) :1229-1235
[4]   The first total synthesis of dragmacidin D [J].
Garg, NK ;
Sarpong, R ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13179-13184
[5]   Conformational control in the rebeccamycin class of indolocarbazole glycosides [J].
Gilbert, EJ ;
Chisholm, JD ;
Van Vranken, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5670-5676
[6]  
GREEN TW, 2005, PROTECTIVE GROUPS OR
[7]   Efficient indole N-detosylation using thioglycolate [J].
Haskins, CM ;
Knight, DW .
TETRAHEDRON LETTERS, 2004, 45 (03) :599-601
[8]   Synthesis and reactivity of azaindoles: Applications in the preparation of bioactive molecules [J].
Le Hyaric, M ;
de Almeida, MV ;
de Souza, MVN .
QUIMICA NOVA, 2002, 25 (6B) :1165-1171
[9]   Catalytic polymer-supported potassium thiophenolate in methanol as a method for the removal of ester, amide, and thioacetate protecting groups [J].
MacCoss, RN ;
Henry, DJ ;
Brain, CT ;
Ley, SV .
SYNLETT, 2004, (04) :675-678
[10]  
MURATAKE H, 1989, HETEROCYCLES, V29, P783