Solid-phase synthesis of N-acyl-N′-carbamoylguanidines

被引:27
作者
Lin, PS [1 ]
Ganesan, A [1 ]
机构
[1] Natl Univ Singapore, Inst Mol & Cell Biol, Singapore 117609, Singapore
关键词
combinatorial chemistry; solid-phase synthesis; thioformamidines; guanidines;
D O I
10.1016/S0040-4039(98)02174-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amino acids immobilized on polystyrene-Wang or Rink amide resin were reacted with p-nitrophenyl chloroformate to give an activated urethane that was displaced by S-methylisothiourea. Following N-acylation with an acid chloride, the thiomethyl group was displaced by primary or secondary amines with the aid of mercury (II) chloride to yield the unsymmetrically substituted title compounds after resin cleavage. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9789 / 9792
页数:4
相关论文
共 19 条
[1]   Natural guanidine derivatives [J].
Berlinck, RGS .
NATURAL PRODUCT REPORTS, 1996, 13 (05) :377-409
[2]  
BUNIN BA, 1998, COMBINATORIAL INDEX
[3]   An efficient procedure for the guanylation of amines using N,N'-bis(benzyloxycarbonyl)-S-methylisothiourea [J].
Chandrakumar, NS .
SYNTHETIC COMMUNICATIONS, 1996, 26 (14) :2613-2616
[4]  
de Deyn P.P., 1992, GUANIDINO COMPOUNDS
[5]  
DEDEYN P, 1997, GUANIDINO COMPOUNDS, V2
[6]   Solid-phase synthesis of N,N′ substituted guanidines [J].
Dodd, DS ;
Wallace, OB .
TETRAHEDRON LETTERS, 1998, 39 (32) :5701-5704
[7]   Solid-phase synthesis of trisubstituted guanidines [J].
Drewry, DH ;
Gerritz, SW ;
Linn, JA .
TETRAHEDRON LETTERS, 1997, 38 (19) :3377-3380
[8]  
Gomes de Souza Berlinck R, 1995, Fortschr Chem Org Naturst, V66, P119
[9]   Solid-phase organic reactions: A review of the recent literature [J].
Hermkens, PHH ;
Ottenheijm, HCJ ;
Rees, D .
TETRAHEDRON, 1996, 52 (13) :4527-4554
[10]   Solid-phase organic reactions .2. A review of the literature Nov 95 Nov 96. [J].
Hermkens, PHH ;
Ottenheijm, HCJ ;
Rees, DC .
TETRAHEDRON, 1997, 53 (16) :5643-5678