Thiazole formation via traceless cleavage of Rink resin

被引:22
作者
Pons, JF [1 ]
Mishir, Q [1 ]
Nouvet, A [1 ]
Brookfield, F [1 ]
机构
[1] Oxford Asymmetry Int, Oxford OX11 4RD, England
关键词
alpha-haloketones; Lawesson's reagent; Rink amide resin; thiazole; traceless;
D O I
10.1016/S0040-4039(00)00748-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The traceless cleavage of Rink amide resin to form thiazoles has been achieved using commercially available reagents. Conversion of Rink amide species to thioamides by use of Lawesson's reagent prepares the resin bound substrates for traceless cleavage. Cleavage using limiting amounts of alpha-haloketones provides thiazole bearing compounds of high purity. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4965 / 4968
页数:4
相关论文
共 13 条
[1]  
[Anonymous], ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANIE.199622881
[2]   Synthesis utilizing insoluble polymers: new reactions and small molecules [J].
Baxter, AD .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1997, 1 (01) :79-85
[3]   Development of a novel silyl ether linker for solid-phase organic synthesis [J].
Boehm, TL ;
Showalter, HDH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6498-6499
[4]  
BUNIN BA, 1998, DOMBINATORIAL INDEX
[5]  
CHENERA B, 1995, J AM CHEM SOC, V117, P11999
[6]   STUDIES ON AMINO-ACIDS AND PEPTIDES .1. SYNTHESIS OF N-BENZYLOXYCARBONYLENDOTHIODIPEPTIDE ESTERS [J].
CLAUSEN, K ;
THORSEN, M ;
LAWESSON, SO .
TETRAHEDRON, 1981, 37 (21) :3635-3639
[7]   The preparation of 2,4-disubstituted thiazoles on solid support [J].
Goff, D ;
Fernandez, J .
TETRAHEDRON LETTERS, 1999, 40 (03) :423-426
[8]  
Jones J.H., 1991, CHEM SYNTHESIS PEPTI
[9]   Solid-phase synthesis of 2-aminothiazoles [J].
Kearney, PC ;
Fernandez, M ;
Flygare, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (01) :196-200
[10]   The current status of heterocyclic combinatorial libraries [J].
Nefzi, A ;
Ostresh, JM ;
Houghten, RA .
CHEMICAL REVIEWS, 1997, 97 (02) :449-472