Synthesis of hydantoins via N,N′-ureas derived from polymer-bound amino acids

被引:5
作者
Bauser, M
Winter, M
Valenti, CA
Wiesmüller, KH
Jung, G
机构
[1] Univ Tubingen, Inst Organic Chem, D-72076 Tubingen, Germany
[2] NMI Reutlingen, D-72768 Reutlingen, Germany
关键词
automated synthesis; combinatorial chemistry; hydantoins; imidazolidinediones; solid phase synthesis;
D O I
10.1023/A:1009639804397
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Starting from carboxy-linked amino acids on trityl functionalized polystyrene resin a highly efficient solid-phase synthesis of hydantoins via N,N'-ureas was elaborated. The polymer-bound hydantoins can be used as scaffolds for further combinatorial transformations, such as alkylation. Cleavage from the resins yielded the corresponding hydantoins in good yields and purities as shown by ESI-MS and HPLC.
引用
收藏
页码:257 / 260
页数:4
相关论文
共 10 条
[1]  
Balkenhohl F., 1996, ANGEW CHEM, V108, P2436
[2]   DIVERSOMERS - AN APPROACH TO NONPEPTIDE, NONOLIGOMERIC CHEMICAL DIVERSITY [J].
DEWITT, SH ;
KIELY, JS ;
STANKOVIC, CJ ;
SCHROEDER, MC ;
CODY, DMR ;
PAVIA, MR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (15) :6909-6913
[3]   Organic chemistry on solid supports [J].
Fruchtel, JS ;
Jung, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42
[4]  
HENESSIAN S, 1996, TETRAHEDRON LETT, V37, P5835
[5]  
HOWIE C, 1990, J CHEM SOC PERK T, V1, P3129
[6]  
JUNG G, 1996, COMBINATORIAL PEPTID
[7]  
KWON KS, 1982, YAKHAK HOE CHI, V26, P111
[8]   Base-promoted solid-phase synthesis of substituted hydantoins and thiohydantoins [J].
Matthews, J ;
Rivero, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6090-6092
[9]   SOLID-PHASE SYNTHESIS OF STRUCTURALLY DIVERSE 1,4-BENZODIAZEPINE DERIVATIVES USING THE STILLE COUPLING REACTION [J].
PLUNKETT, MJ ;
ELLMAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :3306-3307
[10]   THE CHEMISTRY OF THE HYDANTOINS [J].
WARE, E .
CHEMICAL REVIEWS, 1950, 46 (03) :403-470